Every Lana Del Rey Song, Ranked: Critic's List

Born to Die, her 2012 major-label debut, arrived with impossibly high levels of both hype and trepidation, to decidedly mixed initial reactions. Del Rey took the girl-group, Nancy Sinatra pop stylings of the ’60s, and fused it with modern cinematic production and a glamorous, Hollywood-inspired image, to create a kind of hyper-real 21st century Americana. “Lana Del Rey” became an instantly identifiable aesthetic, the same way the likes of David Lynch, Mad Men, Margaret Keane, or Amy Winehouse had before her. The Paradise EP and her epic “Ride” video soon followed, expanding on Born to Die’s themes of romantic fatalism, while galvanizing an emerging cult fanbase that hung on her every word.

In 2013, “Young and Beautiful,” her theme from Baz Luhrmann’s The Great Gatsby, and the Cedric Gervais remix of “Summertime Sadness” made Del Rey a reliable hitmaker, and a household name. And then, with her 2014 sophomore LP Ultraviolence, she burned it all down, trading the hip-hop beats for fiery psych-rock guitars, on songs where she had no interest in coming off as sympathetic. 2015’s Honeymoon indulged in jazz and soul, opening herself back up to the possibility of happiness. On 2017’s Lust For Life, Lana rebooted her image once again, adopting an optimistic, Woodstock-inspired outlook for our uncertain age. The critically beloved Norman Fucking Rockwell, from 2019, was her most complete reinvention yet, turning her into a folk-rock troubadour who’d never seemed more human.

March's Chemtrails Over the Country Club was the opposite of radical, but served a crucial purpose in reconnecting Del Rey with her roots as a singer-songwriter in the American tradition. Her most creatively unburdened album, Chemtrails felt instantly timeless -- cementing her place in the modern canon alongside her Laurel Canyon idols, the likes of Joan Baez and Joni Mitchell.

Through all the controversies, Lana’s artistry has endured. Born to Die has stayed on the Billboard 200 albums chart for almost a full decade, the second-longest charting album by a female solo artist in history. Without intending to, that album became one of the main catalysts for pop’s mid-2010s shift from brash EDM to a moodier, hip-hop-inflected palette. She’s influenced not just her peers, but the next generation of alternative-leaning pop stars: Lorde, Halsey, Billie Eilish, Banks, Sky Ferreira, Father John Misty, Sia, Miley Cyrus, Selena Gomez, Taylor Swift, and now Olivia Rodrigo -- but Lana Del Rey remains utterly inimitable. Now 34, she’s matured into a generational balladeer; yet she’s become more down-to-earth, no longer defined by the tragic figures who once inhabited her songs. She’s often seemed like a figure out of her own time: a ’60s hippie, a jazz singer, an old-Hollywood icon. But the last decade of popular music wouldn’t be the same without her.

Lana’s told so many different stories within and outside of her music, that ranking her individual songs allows a valuable opportunity to take a critical look at her entire body of work. Here, Billboard tries to examine every facet of her identity with equal consideration -- the pop star, singer-songwriter, visual artist, icon. This list includes every commercially available Lana Del Rey song, excluding remixes, YouTube uploads, unreleased tracks, and several Great Gatsby soundtrack cuts that merely sample her voice.

We’ve decided to omit her original indie debut album, 2010’s Lana Del Ray a.k.a. Lizzy Grant, where she wasn’t fully formed -- even down to the spelling of her name. Though the album was briefly issued on iTunes, it was taken down two months later at Lana’s own request, and has never been officially available since. While it’s worth a listen for hardcore fans, it ultimately feels like more of a prologue than a part of the Del Rey songbook. We’ve also excluded her 2020 spoken-word poetry audiobook Violet Bent Backwards over the Grass -- a singular, sprawling work in her catalogue, but not directly comparable to her musical compositions.

That leaves us with 113 fascinating songs, almost all of which are good, and at least 50 of which are absolutely exceptional. See our ranking of all of them below.

113. “Guns and Roses” (Ultraviolence deluxe edition bonus track, 2014)

Many of Lana’s songs have used rock ‘n’ roll imagery to great effect, but “Guns and Roses” does nothing with it. “He loved guns and roses,” she sings repeatedly in the chorus, reminding you of better songs, by her and Guns N’ Roses. Rick Nowels’ production conjures a thick atmosphere, like Tricky with John Bonham drums, but the songwriting is unusually lazy by her standards -- a vague recollection of an unfinished demo. To be fair, Ultraviolence’s bonus tracks may only have been released due to iTunes’ demand for a deluxe edition.

112. “Lolita” (Born to Die deluxe edition bonus track, 2012) 

“Lolita” is cut from the same cloth as “National Anthem” or “Off to the Races,” but its hooks feel tuneless, and its hip-hop beats gaudy and cluttered. The lyrics reference Vladimir Nabokov’s Lolita, but evoke no emotion -- they’re just Lana at her brattiest, referencing icons with little purpose except as cheap signifiers of her taste. At best, “Lolita” is an failed experiment, at worst, a creative dead end. But listening to the far better demo version, you can hear what she had in mind -- it originally sounded like the theme to a ’60s spy film.

111. “Florida Kilos” (Ultraviolence deluxe edition bonus track, 2014)

Co-written by director Harmony Korine for his unproduced film The Trap, “Florida Kilos” -- the least subtle Lana Del Rey song of all time -- romanticizes the drug trade in Florida. Though the song never uses the word “cocaine,” it crams in seemingly every other term for it. With a jauntier guitar-pop feel than the rest of the album, “Florida Kilos” plays like the soundtrack to a group of line-dancing cokeheads with nothing but themselves on their minds.

110. “Lucky Ones” (Born to Die deluxe edition bonus track, 2012)

“Lucky Ones” paraphrases three iconic Bruce Springsteen lyrics in its opening lines: “Let's get out of this town, baby we're on fire/ Everyone around here seems to be going down, down, down.” Unlike those classics, “Lucky Ones” is too thinly sketched to make its written-in-the-stars love story believable.

109. “Is This Happiness” (Ultraviolence deluxe edition bonus track, 2014)

A portrait of two unfulfilled artists trapped in an equally dead-end relationship. “You think you’re Hunter S. Thompson/ I think you’re fucking crazy as the day’s long,” sings Lana, with as little romance as she can muster. With her restrained vocals, and a plain piano accompaniment, “Is This Happiness” just manages to pull at your heartstrings -- even if the song intentionally goes nowhere.

108. “Wait For Life” (Emile Haynie feat. Lana Del Rey, We Fall, 2015)

Lana provides lead vocals on the debut single from Emile Haynie, the main producer behind Born to Die’s cinematic hip-hop sound. The chorus pairs a beautiful melody with grim lyrics: “I wait for life to end/ But it never comes around.” Surprisingly for Haynie, “Wait For Life” has little in the way of drums -- it’s mostly strings and bluesy piano. The production may be lush, but the song’s sadness is one-dimensional. By 2015, Lana was regularly exploring far more nuanced artistic territory.

107. “Burning Desire” (Paradise iTunes bonus track, 2012)

The lowest moments on Paradise felt like a retread of Born to Die, with the same musical elements shuffled around. The closing track on some editions of the EP, “Burning Desire” is the most illustrative example of a mediocre Lana Del Rey song. Her deep alto in the chorus is alluring, but the lyrics are a series of car cliches with little narrative or emotional depth: “I’m driving fast, flash!/ Everyone knows it/ I’m trying to get to you, baby.” The song found its match in its music video, a beautifully empty Jaguar ad.

106. “Season of the Witch” (non-album single, 2019)

Donovan’s 1966 original has become an unlikely standard, evoking the looming cultural paranoia of the mid-’60s. Lana’s interpretation, recorded for the Scary Stories to Tell in the Dark film, is nowhere near as obvious as most slowed-down movie trailer cover songs, but it still feels a bit neutered. At a slower tempo, with less drums, it’s less propulsive; and where Donovan’s voice is sly, charismatic, Lana’s is smooth and ethereal. She makes it more literally witchy, which perhaps misses the song’s metaphor. It’s still a worthy cover, but there’s not much she can subvert about the already-so-subversive original, which has lost none of its potency.

105. “White Mustang” (Lust For Life, 2017)

“White Mustang” isn’t a bad song, but it doesn’t feel notable enough to warrant its own video treatment. Lana describes her jealousy while dating a musician, feeling like a secondary concern to his art. “The day I saw your white Mustang,” repeats the chorus, which treats the car as a stand-in for the man, but never elaborates on that central metaphor. The production is business as usual -- piano, trap drums -- as is the Rich Lee-directed video, even with its admittedly beautiful digital shots of the L.A. skyline.

104. “Don’t Call Me Angel” (Ariana Grande with Miley Cyrus & Lana Del Rey, Charlie’s Angels: Original Motion Picture Soundtrack, 2019)

This bouncy, much-hyped Max Martin-produced single allows all three of its stars to be themselves -- yet they never meet in the middle. Miley’s her usual defiant self, while Ariana’s in femme fatale mode, but it’s Lana who elevates the song into a strange level of camp. As the song abruptly shifts gears into a narcotic halftime bridge, she drops more cliches than in any song since the Paradise era: “I drop it down, I pick it up, I back it off the county line/ I fell from heaven, now I’m living like a devil...” She sticks to her sonic comfort zone, but that only makes her sound even more out of place, both within the song and her own discography -- as “Don’t Call Me Angel” was released just two weeks after Norman Fucking Rockwell. At best, it’s a reminder of how Lana’s successes have come on her own terms, without capitulating to more conventional mainstream pop trends.

103. “Hallucinogenics” (Matt Maeson feat. Lana Del Rey, non-album single, 2020)

A shouty acoustic indie-blues song in the vein of Mumford & Sons, the original solo version of “Hallucinogenics” was a big hit on alternative and rock radio. Maeson’s lyrics conjure up dramatic images (“Pushing past the limit, trippin’ on hallucinogenics/ My cigarette burnt my finger ’cause I forgot I lit it”), but his bombastic delivery crowds out any sense of intimate emotional connection. Lana’s not an obvious choice for a duet partner, but she does bring some warmth to the song, introducing it with a soft verse, and adding prominent backing vocals throughout. She arguably improves the song by tempering its more macho qualities -- yet it doesn’t exactly need her presence, either. A softer version could have made for a good cover, but as it is, “Hallucinogenics” doesn’t play to Lana’s strengths.

102. “God Save Our Young Blood” (Børns feat. Lana Del Rey, Blue Madonna, 2018)

Børns, like Lana, can also seem like a figure out of his time -- as if he emerged from a time machine from the ’70s, with his impossibly high tenor and bell-bottom jeans. The two have real vocal chemistry, but the music feels too off-kilter to be the anthemic pop single it wants to be. Each chorus brings an unnecessary key change, each more disorienting than the last.

101. “Big Eyes” (Big Eyes: Original Motion Picture Soundtrack, 2014)

Its chorus may be nursery-rhyme simple -- “With your big eyes/ And your big lies” -- but “Big Eyes” made the perfect theme for an emotional turning point in Tim Burton’s 2014 film of the same name. Big Eyes was inspired by the life of the artist Margaret Keane, whose signature paintings of big-eyed children became an American phenomenon, all while her husband spent years taking credit for her work. Over brooding minor-key piano and strings, Lana sings as if she’s the voice inside Keane’s head. Her suspicions of her husband’s emotional manipulation come true, culminating in a lyric that sums up Lana’s own career -- “It’s amazing what women in love will do.” Still, “Big Eyes” doesn’t particularly stand out in Lana’s discography -- it’s ultimately too tied to its usage in the film.

100. “Religion” (Honeymoon, 2015)

A tender, minor-key ballad about finding true love after some troubled times. Genuinely moving, but neither Lana’s narrative -- “It never was about the money or the drugs/ For you, there’s only love” -- nor the spaghetti-western guitars build to the climax the song deserves.

99. “Bel Air” (Paradise, 2012)

Written around a delicate piano motif reminiscent of “Walking in the Air,” Howard Blake’s theme from the 1982 animated short The Snowman, Lana tells a fairytale of a woman waiting to meet her lover in heaven. “Bel Air” is unusual for a Lana composition, in that it’s major-key and haunting, but the song doesn’t develop as much as it should -- it just travels in circles for most of its four minutes.

98. “Blue Velvet” (Paradise, 2012)

Recorded to promote her H&M Fall 2012 campaign, Lana’s reedy lower register is perfect for the traditional jazz-pop of “Blue Velvet.” Apart from the programmed drums, it’s a straightforward cover of Bobby Vinton’s definitive reading of the song. The music video is suitably eerie, but it’s even stranger to see the titular scene from David Lynch’s Blue Velvet repurposed for an advertisement, even if it’s one as memorable as this.

97. “American” (Paradise, 2012)

A love song whose lyrics might read as silly -- “Elvis is the best, hell yes/ Honey, put on that party dress” -- if not for the tenderness of Lana’s delivery, and the gentle string arrangement behind her. “Be young, be dope, be proud/ Like an American,” goes the chorus -- dreamlike, alluring enough that you might buy into her fantasy… but ultimately, the sentiment is one-dimensional. Unlike in some of her later, more powerfully optimistic tracks, her flag-waving nostalgia isn’t grounded by any sense of reality. Lana would distance herself from such overt displays of patriotism just a few years later.

96. “Without You” (Born to Die deluxe edition bonus track, 2012)

Lana plays a starlet who has it all -- “money, notoriety, and rivieras” -- but none of that matters when she’s with her true love. “Without You” feels a tad too light to belong on Born to Die proper, but the chorus does have one of her prettiest melodies: “I’ve nothing without you…” Interestingly, it’s her first song to explicitly value love over fame.

95. “In My Feelings” (Lust For Life, 2017)

It’s unlike Lana to openly admit that she “fell for another loser,” but “In My Feelings” is her shadiest song -- an almost alt-R&B track allegedly inspired by her brief dalliance with G-Eazy. In fact, she’s never depicted a lover with so few redeeming qualities: “Get that cigarette smoke out of my face/ You’ve been wastin’ my time while you’re takin’ what’s mine.” In the chorus, she finally regains her sanity: “Who’s doper than this bitch?/ Who’s freer than me?.../ I’m feelin’ all my fuckin’ feelings!”

94. “Art Deco” (Honeymoon, 2015)

Honeymoon is an excellent album, but starting with "Art Deco" at track seven, it can get too laid-back for its own good. An ode to young women and nightlife, “Deco” is more sleepy than invigorating, though that’s partly by design -- it’s a song for comedowns, not parties themselves. Rick Nowels and Kieron Menzies’ lush orchestral soundscapes can occasionally overwhelm Lana’s thinner compositions.

93. “Salvatore” (Honeymoon, 2015)

Is “Salvatore” supposed to be ridiculous? Even four years later, it’s hard to tell. A dour, yet campy ballad about a affair with a classically handsome Italian man, “Salvatore” has an unforgettable chorus where Lana babbles semi-Italian phrases out of context: “Ahhhhh, ahhhh, cacciatore.../ Limousines.../ Ciao amore.../ Soft ice cream.” You could interpret the song as a bourgeois woman distracting herself from her distant lover by indulging in hedonistic pleasures… I guess. When Lana later called Honeymoon “like a vanity project, just for me,” “Salvatore” must have been what she had in mind.

92. “Let Me Love You Like a Woman” (Chemtrails Over the Country Club, 2020)

A decidedly underwhelming choice for a lead single, “Let Me Love You Like a Woman” signaled that Chemtrails would not be a particularly pop-leaning era. A sleepy piano ballad, it’s not even a standout on the album itself. It’s best appreciated on its own terms, as a song where Lana pledges a tender, lasting love over sweet -- some would say rote -- melodies. Unusually for Lana, it’s a song that conjures little intrigue or imagination beyond its brief three minutes. Unlike the studio version, her live Tonight Show performance features backing vocalists, and simply feels fuller and more alive.

91. “24” (Honeymoon, 2015)

“There’s only 24 hours in a day/ And half of those, you lay awake with thoughts of murder and carnage,” sings Lana -- about a man she supposedly loves! “24” plays as a brooding, Bond-like orchestral warning to herself and the listener: “If you lie down with dogs, then you’ll get fleas/ Be careful of the company you keep.” The song’s most memorable for its ending, where Lana wails, “You’re hard to reach!” -- and the music drops out dramatically, for one thrilling measure.

90. “Prisoner” (The Weeknd feat. Lana Del Rey, Beauty Behind the Madness, 2015)

Lana Del Rey and The Weeknd’s careers have many parallels. Their music’s defined by stories of tortured romance, they both made the unlikely leap from viral success to the pop charts… and they’re two of the only singer-songwriters in 2010s pop who tell complete stories through their lyrics. As Abel Tesfaye said in 2015, “Me and Lana have been friends for a long time. I’ve inspired her, she’s inspired me... She is the girl in my music, and I am the guy in her music.” “Prisoner” is an arena-sized alt-R&B track that’s suitably exciting, but could have aimed much higher. Though Lana was Abel’s first female guest vocalist, she feels too much like an extension of him, rather than a much-needed feminine counterpoint to his usual tales of debauchery. They’d have more meaningful collaborations in the years to come.

89. “Carmen” (Born to Die, 2012)

The rare Lana song that’s written in third-person, “Carmen” tells of a teenage girl who’s driven to sex work by her alcoholism. Lana plays mournful verses against bittersweet choruses: “Her mind’s like a diamond.../ She’s still shining/ Like lightning.” But musically, it’s one of the more one-dimensional tracks on Born to Die, and the collage-style video makes “Carmen” feel even more claustrophobic… until it ends with a coda of a woman dancing to a gentle Erik Satie piano waltz -- perhaps, a moment of hope?

88. “Summertime (The Gershwin Version)” (non-album single, 2020)

After covering “Doin’ Time,” it was only a matter of time before Lana found her way to the original song Sublime were referencing. Her interpretation of “Summertime,” one of George Gershwin’s most iconic works in the Great American Songbook, is suitably lush and indulgent, with a touch of New Orleans swing. Though the chords and ghostly backing harmonies feel melancholy, there’s an undeniable joy to Lana’s drawn-out vocal delivery. It’s not a major release for her, nor an all-time great reading of the song, but she breathes just enough new life into an old classic -- and in doing so, draws a connection from Gershwin to Sublime to herself, further evidence of her being one of the few modern musicians who’s in dialogue with the full last century of popular song.

87. “Bartender” (Norman Fucking Rockwell, 2019)

Over baroque piano reminiscent of “Bel Air,” “Bartender” finds Lana dreaming of escape from onlookers’ prying eyes: “I bought me a truck in the middle of the night.../ Photo-free exits from baby’s bedside/ ’Cause they don't yet know what car I drive…” This version of Lana’s in love with a bartender, but older and wiser, resists temptation: “Baby, remember, I’m not drinking wine/ But that Cherry Coke you serve is fine...” "Bartender” is dreamy and inscrutable, like a parable with no moral to its story. In a 2018 interview with Pitchfork, Lana called it “this weird track... that doesn’t belong to a record yet.” “Bartender” does feel out of place near the tail end of Norman Fucking Rockwell, but on its own, it’s a peculiar little ditty that defies categorization.

86. “The Next Best American Record” (Norman Fucking Rockwell, 2019)

“The Next Best American Record” is another of Lana’s portraits of an artistic and romantic relationship, where she describes a lover who sounds like Eddie Vedder or Jackson Maine: “He was ’70s in spirit, ’90s in his frame of mind...” She sings fondly of their collaborations -- “We were so obsessed with with writing the next best American record/ ’Cause we were just that good” -- but the chorus instead shifts to a banal Lana-ism, almost like her protagonist’s distracted by her love: “Whatever’s on tonight, I just wanna party with you!” The song culminates in a bridge lyric that pays tribute to him -- “I see you for who you really are/ Why the thousands of girls love/ The way Bill plays guitar” -- but ends with the sinister sound of glass shattering.

85. “The Blackest Day” (Honeymoon, 2015)

Honeymoon’s back half can feel like a series of distant, beautiful dirges -- not always for the better -- but “The Blackest Day” embodies that coldness with graceful melodies and production. The song finds Lana going through the five stages of grief, as she attempts to process a breakup. Though she pens two intriguing turns of phrase, “I’m not simple, it’s trigonometry,” and “All I hear is Billie Holiday,” she shies away from exploring either -- choosing instead to immerse herself completely in her heartbreak.

84. “Once Upon a Dream” (Maleficent: Original Motion Picture Soundtrack, 2014)

In Disney’s 1959 film Sleeping Beauty, “Once Upon a Dream” soundtracks a chirpy courtship scene between Aurora and the prince, as performed by Mary Costa and Bill Shirley. As the theme from Maleficent, a reimagining of the fairytale starring Angelina Jolie, Lana’s take is darker and slower -- yet more hopeful than much of her early discography. She imbues those familiar words -- “I know you, I walked with you once upon a dream” -- with a vivid sense of memory, retelling a old story the way she chooses to remember it.

83. “God Bless America – And All the Beautiful Women in It” (Lust For Life, 2017)

A ’60s hippie sentiment with drums by trap producer Metro Boomin, this is a different kind of anthem to 2012’s “American” -- one that acknowledges the political turmoil of the moment, that treats its title as a demand for peace. “God bless America,” croons Lana in the chorus, before two “Paper Planes”-style gunshots ring out, just in case you missed her point. But on another level, the song is a loving tribute to all the women whose strength inspires her: “I feel your arms all around me/ In the air or the streets of the city/ Feels like I am free…”

82. “Black Beauty” (Ultraviolence deluxe edition bonus track, 2014)

A gentle rejoinder to a lover who’s too goth to live: “You said if you could have your way/ You’d make it night time all today/ So it’d suit the mood of your soul.” He won’t return Lana’s affections, and she can’t change him, but she remains enthralled by his beauty anyway. “Black Beauty” has similar themes to “Shades of Cool,” but it’s more plainspoken, wistful. Curiously, this bonus track is Lana’s only collaboration with Paul Epworth, the producer and songwriter behind many of Adele and Florence + the Machine’s biggest songs, but who doesn’t leave his usual maximalist stamp here.

81. “I Can Fly” (Big Eyes: Original Motion Picture Soundtrack, 2014)

“I Can Fly” plays over the end credits to Big Eyes, a melancholy yet triumphant coda to Margaret Keane’s story. In the verses, Lana’s vocals are still muted and hesitant, but she soars in the chorus -- as if she’s reliving a traumatic memory, before realizing she’s already survived it. Lana clearly sees much of herself in Margaret Keane, who by the end of the film, is finally free to make art that’s not just about sadness, that embodies the full expression of the human spirit. “I had a dream that I was fine/ I wasn’t crazy, I was divine...”

80. “Woman” (Cat Power feat. Lana Del Rey, Wanderer, 2018)

Cat Power might be Lana’s closest immediate predecessor -- a sometimes uncomfortably raw songwriter and performer, who reinvented herself as a soulful troubadour in the second half of her career. “Woman” starts as a sparse cowboy blues song, but accelerates into its choruses, building in urgency each time. Lana only sings a few lines, mostly backup, but her presence lends crucial moral support. Though it’s not quite an anthem, it is a defiant, yet warm feminist declaration that plays on both artists’ histories in the public eye: “I’m a woman of my word, now haven't you heard?/ My word's the only thing I’ve ever needed.”

79. “Groupie Love” (feat. A$AP Rocky, Lust For Life, 2017)

This Lust For Life promo single might be the least critical ode to the groupie since the heyday of glam metal. Still, Lana so vividly realizes the emotions of a starry-eyed young fan that you can’t help but buy into her fantasy. The lush production, and the slow, almost chopped-and-screwed “groupie looooove” chorus are stunning. Lana’s had a few previous encounters with A$AP Rocky, her “National Anthem” video co-star and unlikely kindred spirit, but Lust For Life marks their first official set of musical collaborations. In his second feature on the album in a row, Rocky plays a Prince Charming who may or may not have a dark side: “Love girls, you and I, so who do we trust?/ You and I ’til the day we die.”

78. “You’ll Never Walk Alone” (The End of the Storm [Official Soundtrack], 2020)

“You’ll Never Walk Alone” is a song with a long, unbroken history. Written by Rodgers and Hammerstein for the 1945 musical Carousel, the 1963 cover by Gerry and the Pacemakers was adopted as the Liverpool Football Club’s official anthem -- and has remained an iconic crowd singalong ever since. A Liverpool fan herself, Lana contributed a version for the club’s documentary The End of the Storm. She sings largely a cappella, in an exposed, wavering vibrato, before she’s overtaken by strings, piano, and a baritone choir. When her voice returns at the climax almost two minutes later, she hits a stunningly beautiful high G. Though there’ve been hundreds of recorded covers, Lana’s might be the most ethereal interpretation since the operatic original -- even if she’s not present for half of her own recording.

77. “I’ll Be Home for Christmas” (Kacey Musgraves feat. Lana Del Rey, The Kacey Musgraves Christmas Show, 2019)

Recorded for Musgraves’ Amazon Prime Christmas special, Lana joins Kacey for a stripped-down cover of this Bing Crosby standard. The two typically take very different approaches to melancholy -- Lana’s is grand and existential, Kacey’s small and intricate -- but here, Lana matches Kacey’s energy, singing at barely above a whisper. They manage to make one of the saddest Christmas songs even sadder, and the results are magical. 

76. “Stargirl Interlude” (The Weeknd feat. Lana Del Rey, Starboy, 2016)

Halfway through The Weeknd’s third official album, Lana Del Rey takes the reins. “I shouldn’t cry, but I love it, starboy,” she sings, higher than she ever has on record. “Stargirl Interlude” is more overtly sexual than much of her work, but more spiritual than almost any of The Weeknd’s; a perfect union, if only it were longer than two minutes.

75. “Burnt Norton (Interlude)” (Honeymoon, 2015)

Over a crackling, ambient loop, Lana reads the opening lines of “Burnt Norton,” a T.S. Eliot poem about the fleeting, circular nature of time. Rather than co-opting the poem for her own artistic narrative, she presents herself as a vessel for Eliot’s words. Though it’s too short to rank any higher, “Burnt Norton” is a complete recording in and of itself, one that perfectly embodies Honeymoon’s sense of serene stillness.

74. “When the World Was at War We Kept Dancing" (Lust For Life, 2017)

“Is it the end of an era?/ Is it the end of America?” Lana implores the listener to look to history: “No, it's only the beginnin’/ If we hold on to hope, we’ll have our happy ending...” The lyrics may not add up to a definitive political statement -- Lana’s rarely do -- but the music cannily embodies the uncertainty of the modern age. The titular chorus is mesmerizing, as Del Rey coos in a high falsetto while trap hi-hats twirl around her.

73. “Summer Bummer” (feat. A$AP Rocky and Playboi Carti, Lust For Life, 2017)

A return to hip-hop stylings not heard since Born to Die, this Lust For Life promo single opens with Lana’s optimistic vocals over dour, muted piano -- “It’s never too late to be who you wanna be/ To say what you wanna say” -- until the song transitions to a buzzy trap beat co-produced by Boi-1da. It’s equally novel to hear A$AP Rocky rap with far more energy than we’re used to on a Lana album, as it is to hear her drawling in a triplet flow in the third verse. Over ad-libs by Playboi Carti, Rocky teases a flirtation that might, but probably won’t outlast the season: “She just might become my lover for real/ I might fuck with her all summer for real...” It evokes a kind of summertime sadness she’s never documented before -- sweaty, uncomfortable, delirious.

72. “Happiness is a butterfly" (Norman Fucking Rockwell, 2019)

Each stanza of “Happiness is a butterfly” contradicts the last, like its opening lines: “Do you want me or do you not?/ I heard one thing, now I'm hearing another…” Over Jack Antonoff’s dour piano chords, Lana waxes philosophical about life’s uncertainties: “Happiness is a butterfly/ Try to catch it, like, every night/ It escapes from my hands into moonlight…” Will she find true love with the man of this particular song?

She responds with a classically Lana Del Rey turn of phrase: “If he’s a serial killer, than what’s the worst/ That can happen to a girl who’s already hurt?” Her mindset calls back to Ultraviolence -- she’s so fatalistic that death might be an improvement… but does it even matter? She keeps coming back to one phrase: “Baby, I just wanna dance with you.” Music and dance may not fix anything, but it’s all Lana has in the moment, forever chasing that butterfly.

71. “Swan Song” (Honeymoon, 2015)

As early as 2012, Lana Del Rey was dramatically teasing her retirement: “I don’t think I’ll write another record… I feel like everything I wanted to say, I’ve said already.” “Swan Song” almost makes good on that threat: “And I will never sing again/ And you won’t work another day.../ It will be our swan song...” And yet, “Swan Song” is nothing more than a fantasy, more minor-key than hopeful. Sometimes you need to visualize a future before you choose not to go down that path.

70. “Looking for America” (non-album single, 2019)

Released in the wake of the El Paso and Dayton mass shootings, “Looking for America” is Lana’s immediate response to the country’s epidemic of gun violence. Over Jack Antonoff’s minimal fingerpicked guitar, she sings about the nostalgic America we so often depict in art, that lives in our memories: “One without the gun, where the flag can freely fly/ No bombs in the sky, only fireworks when you and I collide.” With great sadness and empathy, Lana shows us how violence affects everyone, down to our most intimate personal emotions. The sad punchline -- “it’s just a dream I had in mind...”

69. “Beautiful People Beautiful Problems” (feat. Stevie Nicks, Lust For Life, 2017)

Stevie Nicks has always been one of Lana’s biggest influences in both music and spirit, two self-proclaimed “witchy sisters” who’ve carved their own paths through popular music. So it’s thrilling to hear the two sing together as peers, on a composition that’s worthy of Stevie’s one-of-a-kind presence. Much like The Beatles’ “Getting Better,” “Beautiful People Beautiful Problems” sets dark verse lyrics to much brighter music -- “Green is the planet from the eyes of a turtle dove/ ’Til it runs red, runs red with blood…” But the chorus is more uplifting, and a little self-deprecating: “We’re just beautiful people with beautiful problems.../ But we gotta try/ Every day and night.” Even musical icons can’t pretend to have all the answers, but they’ll keep searching.

68. “Don’t Let Me Be Misunderstood” (Honeymoon, 2015)

“Don’t Let Me Be Misunderstood” was a canny nod to Lana’s reputation, and her second album in a row to end with a Nina Simone cover. Just three years after Born to Die, she was already working on rehabilitating her controversial image: “Don’t you know, no one alive can always be an angel?/ When everything goes wrong, you see some bad…” The Lana of old might have elevated this into melodrama to rival Nina’s original, but instead, she delivers a surprisingly breezy interpretation. It doesn’t feel like some weighty artistic statement -- she just wants to set the record straight, while putting her stamp on a timeless song.

67. “Flipside” (Ultraviolence deluxe edition bonus track, 2014)

“Are you gonna hurt me now?/ Or are you gonna hurt me later?” With just her voice and Blake Stranathan’s fuzzed-out guitar, “Flipside” tells a sad narrative with a gentle, empathetic touch. Lana sings about letting go of an unreliable lover, at least for now: “You caught me once/ Maybe on the flipside you could catch me again.” He may have dominated their relationship, but she gets the last word. With its grungy feel, “Flipside” is also the rare Lana song that references the recent past -- the ’90s -- and spiritual predecessors like Hole and PJ Harvey.

66. “Diet Mountain Dew” (Born to Die, 2012)

Like a ’60s girl-group song with hip-hop drums, “Diet Mountain Dew” resembles a more polished version of Lana’s indie debut album, Lana Del Ray a.k.a. Lizzy Grant. Though she’s still singing about a not-so-great relationship, the song’s playfully wistful -- “Never was there ever a girl so pretty/ Do you think we’ll be in love forever?” “Diet Mountain Dew” was an early fan favorite, including the original trip-hop version Lana uploaded to YouTube in 2011. But she’s rarely played the song live, and it feels like she’s outgrown it in the years since.

65. “Million Dollar Man” (Born to Die, 2012)

“I don't know how you get over, get over/ Someone as dangerous, tainted, and flawed as you,” sings Lana, in an bluesy ballad that’s garnered comparisons to Fiona Apple. Like many of her early songs, “Million Dollar Man” is about being seduced by beautiful surfaces, oblivious to the harm that men can do because they’re charming. “You’re screwed up and brilliant/ You look like a million dollar man/ So why is my heart broke?” She asks, but she’d yet to find the answer.

64. “California” (Norman Fucking Rockwell, 2019)

Norman Fucking Rockwell’s fourth song in a row about unconditional love, “California” is the most ’70s rock-styled track Lana’s ever recorded, with its fuzzed-out guitars and leisurely double-tracked vocals. In the verses, she addresses a lover in the present tense: “You don’t ever have to be stronger than you really are/ When you’re lying in my arms.” But then she reveals that they’re long gone: “You said to a friend that you wish you were doing better/ I wanted to reach out, but I never said a thing…”

In the chorus, drums and guitars build on a melancholy chord progression, as if she’s on a jet plane flying away from her loved one: “If you come back to America, just hit me up/ We’ll do whatever you want, travel wherever how far.../ I’ll pick up all of your Vogues and all of your Rolling Stones.” “California” connects the dots between two of Lana’s most powerful depictions of regret: the personal nostalgia of “Old Money,” where she dreams of rekindling an old relationship; and the cultural nostalgia of “The greatest,” where she laments the decline of American rock ‘n’ roll and popular culture. “California” isn’t quite as vivid as either of those songs, but there’s still comfort to be found in its familiar melodies.

63. “Gods and Monsters” (Paradise, 2012)

Over slow, insistent drums, Lana tells a Los Angeles tale worthy of Mulholland Drive or The Neon Demon. Playing both omniscient narrator and doomed ingenue, she trades her soul for success in the music industry: “Like a groupie incognito, posing as a real singer/ Life imitates art!” Lana’s protagonist finds her idea of heaven, yet she’s also lucid enough to see that it’s “innocence lost,” a beautiful tragedy. Though it wasn’t a single, “Gods and Monsters” received quite the music video tribute when Jessica Lange covered it in American Horror Story: Freak Show.

62. “Lust For Life” (feat. The Weeknd, Lust For Life, 2017)

“Lust For Life” is Lana’s first title track that doesn’t feel like a grand statement, but it is one of her most positive depictions of sexuality, the “lust for life [that] keeps us alive.” And it is a thrill to hear Lana and The Weeknd sing such sweet melodies, channeling ’60s girl groups like the Shangri-Las and the Angels over booming modern pop production -- one of her two collaborations with Max Martin. Like “Love,” “Lust For Life” is a bubblegum pop song at heart. But while “Love” feels perfect in its simplicity, “Lust For Life” hints at hidden depths that go unexplored: The song interpolates "Invictus," the poem by William Ernest Henley -- “We’re the masters of our own fate/ We’re the captains of our own souls” -- but the lyrics don’t elaborate upon those existential themes, making it the rare Lana Del Rey song that isn’t dark enough.

61. “Cherry” (Lust For Life, 2017)

“Cherry” is unusually sour and cynical by Lust for Life’s standards. Lana describes a strange relationship, built on her own sacrifice, that constantly ruins her: “Love, is it real love?/ It’s like smilin’ when the firin’ squad’s against you/ And you just stay lined up.” “Cherry” transposes a ’60s-style folk song onto dramatic synth bass and sampled drums -- a terse combination that just works.

60. “Radio” (Born to Die, 2012)

“Radio” opens with the sound of strings and crackling vinyl, as Lana drawls a melody reminiscent of the 1940s: “Not even they can stop us now…/ Boy, I’ve been raised from the dead.” She celebrates her newfound success, and she leaves her troubles in the rear-view mirror -- “Baby, love me ’cause I’m playing on the radio!” But even Born to Die’s sweetest song has a little venom. She cusses, and ends each chorus with a shoutout to her doubters: “How do you like me now?”

59. “Breaking Up Slowly” (Chemtrails Over the Country Club, 2021)

“Breaking Up Slowly” opens not with Lana’s voice, but that of her co-writer Nikki Lane, sounding remarkably like Stevie Nicks’ reedy contralto. With its country-blues style, it’s as much Lane’s song as Del Rey’s; a plea to let go of doomed relationships, not prolong the agony. “I don’t wanna live with a life of regret/ I don’t wanna end up like Tammy Wynette,” croons Lane, alluding to Wynette’s tumultuous private relationship with fellow country icon George Jones. Although the song sounds traditional, it’s revisionist in spirit -- acting as a direct rejoinder to Wynette’s most (in)famous song, “Stand by Your Man.” The Lana Del Rey of Ultraviolence would have indulged in the painful fantasy of love at any cost; but on Chemtrails, she’s committed to the reality of the situation. Unlike the rest of the album, there’s no musical uplift to be found, even if the lyrics are ultimately optimistic: “It's hard to be lonely, but it's the right thing to do.”

58. “Dark Paradise” (Born to Die, 2012)

At first, “Dark Paradise” seems to be about an ex -- until Lana reveals that the song is a literal lament: “Your soul is haunting me.../ But I wish I was dead/ Dead like you.” Though the music’s thumping and cinematic, she delivers those lines so casually that it’s shocking. For years, listeners debated -- was Lana glamorizing feminine suffering? Or was she simply expressing her honest, morbid thoughts? When she made a similarly infamous statement in a Guardian interview -- “I wish I was dead already” -- none other than Frances Bean Cobain criticized her for romanticizing suicide. Many of Lana’s songs thrive on such uncomfortable tension, even ones as poppy and melodic as this one.

57.  “Yosemite” (Chemtrails Over the Country Club, 2021)

A Lust For Life-era recording that finally found its way onto Chemtrails, “Yosemite” sees Lana looking upon a relationship with no regrets. Echoing “Venice Bitch,” she looks forward and back at the same time: “Seasons may change/ But we won’t change/ Isn’t it sweet how we know that already?” She’s often sounded like an old soul, but she’s never sung from the perspective of a much older woman before. Alongside Rick Nowels’ fingerpicked steel-string, her vocals were recorded in a single take. “Yosemite” is one of her most haunting pieces of music, yet aside from a reference to “television static,” there’s little darkness to be found in the lyrics. In the chorus, she sums up the defining theme of Chemtrails, her philosophy of unconditional love and artistic expression: “We did it for fun, we did it for free/ I did it for you, you did it for me/ We did it for the right reasons.”

56. “Heroin” (Lust For Life, 2017)

Lana’s own favorite song from Lust For Life finds her musing on an old ex’s fatal overdose. She ruminates on the dark side of California -- the air thick with organs, mellotrons and muted drums -- and what drives people to self destruction: “Topanga’s hot today, Manson’s in the air/ And all my friends have gone, ’cause they still feel him here…” But this Lana, in 2017, is no longer living in the torment of “Yayo” and “Cruel World.” She’s older and wiser, but the past still pulls her back in: “The facts of life can sometimes make it hard to dream.” “Heroin” offers no resolution, but it leads directly into “Change” and “Get Free,” the album’s ending suite: “Makes me feel like I can change/ All of my evil ways and shit/ I’d be lying, if I said I wasn’t sick of it.”

55. “Tomorrow Never Came” (feat. Sean Ono Lennon, Lust For Life, 2017)

“Tomorrow Never Came” might be Lana’s most overtly nostalgic song, a pastoral folk-rock dream that’s utterly transporting. But as she recalls the most idyllic moments of a relationship, she also remembers that it ended. “You said you’d love me like no tomorrow/ I guess tomorrow never came...”

Ironically, Lana’s present reality is a kind of utopia: “Lennon and Yoko, we would play all day long/ ‘Isn’t life crazy?,’ I said now that I’m singin’ with Sean!” Sean Ono Lennon, who also played the majority of the song’s instruments, sounds almost exactly like his father -- bringing an indefinable magic that you rarely hear on “retro” songs. Nostalgia has its limits, but the past lives on through them, and us, to rewrite the future.

54. “Cola” (Paradise, 2012)

“My pussy tastes like Pepsi cola,” drawls Lana, in an opening line that left many shook. “Cola” depicts a world that’s glamorous, tempting, and utterly amoral -- where you can have any pleasure you like, if you can drive fast enough to escape the consequences. “Come on baby, let’s ride.../ I know your wife and she wouldn't mind/ We made it out to the other side...” It’s one of the more thrilling tracks in her discography, culminating in the the horror-film shriek she deploys in the bridge.

In those early years, Lana made you believe she was living out her Hollywood fantasies, whether you liked her or not. But recently, reality has brought “Cola” back down to earth: The song’s once-cheeky nod to Harvey Weinstein, who she’d been photographed with at the time -- “Harvey’s in the sky with diamonds and he’s making me crazy” -- feels uncomfortable, ever since the specifics of his sexual abuse allegations have gone public. Lana’s since committed to retiring “Cola” from her live shows, explaining, “That would be the only right thing to do.”

53. “Body Electric” (Paradise, 2012)

Of the many origin stories Lana’s told, “Body Electric” is the most melodramatic. Heartbroken over an ex-boyfriend, she discovers herself through dance and music. Over thundering drums and Western guitars, she’s reborn as an artist: “I sing the body electric.../ I’m on fire!” Borrowing its manifesto from a famous Walt Whitman poem, “Body Electric” lays out Lana’s creation myth, her earliest inspirations: “Elvis is my daddy/ Marilyn’s my mother/ Jesus is my bestest friend.”

All three icons appear in Tropico, the 2013 short film directed by Anthony Mandler, where Lana portrays a modern Eve, cast out of the garden of Eden. In the real world, she becomes a stripper who liberates herself by robbing her rich older clients, and is then readmitted to heaven. Set to “Body Electric,” “Gods and Monsters,” and “Bel Air,” Tropico is overloaded with heavy-handed symbolism, pushing her early obsession with Hollywood doom-and-gloom to its breaking point. “Body Electric” is particularly compelling, but she couldn’t possibly make songs that were even more fever-pitched and theatrical. She’d soon outgrow this version of the Lana Del Rey persona.

52. “Fuck it I love you” (Norman Fucking Rockwell, 2019)

A weird, offbeat surf-pop ditty that opens with a confession: “I like to see everything in neon/ Drink lime green, stay up ’til dawn/ Maybe the way that I’m living is killing me…” Lana can’t outrun her past, but in the chorus, she throws her cares to the wind: “Dream a little dream of me/ Make me into something sweet/ Turn the radio on, dancing to a pop song/ Fuck it I love you!” It’s as if she’s not just singing to a lover, but the state of California itself.

Though the song’s mostly minor-key, it’s full of playful little oddities: those rising and falling synths in the chorus, and Lana’s almost mumbled pre-chorus, with its dissonant vocal harmonies. Curiously, the CD master -- likely an older version -- replaces the ’60s pop drums with half-time trip-hop beats; a more somber, but less compelling interpretation. The music video, the first half of a double feature with “The greatest,” depicts Lana singing and surfing in slow-motion -- a spiritual experience that ends under the comforting sound of crashing waves.

51. “Dance Till We Die” (Chemtrails Over the Country Club, 2021)

Inspired by a night spent dancing with Joan Baez, Lana’s first verse acknowledges her personal relationships with four of her idols: Baez, Joni Mitchell, Stevie Nicks and Courtney Love. Like Lana herself, these four women are cultural symbols, yet real, ordinary human beings too. She’s equally inspired by both sides of them, and how they never rest on their laurels: “We won’t say when, we won’t ask why/ We won’t stop dancin’ ’til we die.” Most of the song is a ballad, backed by Jack Antonoff’s warm, understated instruments -- so when the bridge suddenly slips into a New Orleans blues groove, it’s as if you’ve drunkenly stumbled into a club on Bourbon Street too. That raucous, celebratory moment -- and Lana’s spectacular vocal -- lasts just 30 seconds before returning to the original instrumental. The glitz and glamour will fade, yet Lana Del Rey remains, the eternal troubadour.

50. "How to disappear" (Norman Fucking Rockwell, 2019)

When Lana and Jack Antonoff premiered “How to disappear” live in late 2018 with just piano and vocals, it was utterly disarming. The studio version is a ’60s soul song with subtle, disorienting electronic production that amplifies the strangeness of the lyrics. “How to disappear” is driven by a oddly figurative Lana narrative -- like a moral parable without a clear answer. In the verses, she describes men from a distance, as if they’re figures from Bruce Springsteen’s Nebraska. To John, she sings, “All of the guys tell me lies, but you don’t/ You just crack another beer/ And pretend that you’re still here” -- like he’s the man from “Video Games,” from another perspective. To Joe, she pledges, “I love that man like nobody can/ He moves mountains and pounds them to ground again…”

In each chorus, the instruments drop out as she sings “This is how to disappear,” mourning how they’ve vanished from her life. The third verse jumps ahead to her now-idyllic life: “Now it’s been years since I left New York/ I’ve got a kid and two cats in the yard…” Lana makes a promise -- “I’m always going to be right here/ No one’s going anywhere” -- but the song ends abruptly, with barely any time to process its resolution. “How to disappear” finds Lana swimming against the currents of time to deliver her message: she’ll be here for you, even if you’re not.

49. “Music to Watch Boys To” (Honeymoon, 2015)

“I see you’re going/ So I play my music, watch you leave...” On Honeymoon’s second single, Lana bids farewell to a lover by shutting out the world, “singing soft grunge just to soak up the noise.” It’s extraordinarily difficult to make compelling music about passivity, but Honeymoon’s best songs manage to be dramatic and meditative in nature.

“Music to Watch Boys To” casts Lana as a detached observer of her own fate, as if she’s witnessing her emotions secondhand. “I press record and watch you leave,” she sings, already prepared to document her experience through art. Though producers Rick Nowels and Kieron Menzies conjure a vague, hazy atmosphere, like Beach House’s dream pop with shades of ’60s exotica, the song is never more alluring than in its extended a cappella intro -- pure, undistilled Lana Del Rey.

48. “Fucked My Way Up to the Top” (Ultraviolence, 2014)

Ultraviolence’s most sardonic, morbidly funny song, “Fucked My Way Up to the Top” garnered immediate attention for its cutting lyrics. When asked about the song by Grazia magazine, Lana stated: “It’s about a singer who first sneered about my allegedly not authentic style, but later she stole and copied it.” Though never confirmed, fans have speculated about its subject being Lady Gaga, Lorde, or even her own past relationship with a label executive.

Diss tracks -- if you even call this one -- rarely contain this much self-loathing. Lana spends most of the song taking shots at her protagonist, a singer with more vanity than talent. But even as she’s being shady -- “Mimicking me’s a fucking bore” -- she finds points of empathy. “Need you baby, like I breathe you baby,” she repeats in the bridge, as her desperation blurs the lines between the character she’s playing, and the “real” Lana.

In 2014, people still genuinely thought of Lana Del Rey as an “industry plant,” a faux-sad-girl flash in the pan with no sense of irony. She’d eventually prove them wrong -- in part by making an album that absorbed those criticisms, and showed us how it felt to endure them. Isn’t every artist a narcissist, on some level?

47. “Coachella – Woodstock in My Mind” (Lust For Life, 2017)

This Lust For Life promotional single was inspired by Lana’s experience at that year’s Coachella. In her words, “I had complex feelings about spending the weekend dancing whilst watching tensions [with] North Korea mount.” “Coachella – Woodstock in My Mind” sounds like the music of today’s youth, mixed with that of their parents; hippie folk-rock sentiments set to melodic alt-R&B. Watching the kids celebrate at Coachella, Lana wonders what their future will look like. Searching for answers, she looks upward, in a chorus filled with wonder: “I’d trade it all for a stairway to heaven.../ I’d trade the fame and the fortune and the legend/ I’d give it all away if you give me just one day to ask him one question...”

The truth is, reality isn’t always so rose-tinted. Modern music festivals are as much about the social climbing as the music, and the original Woodstock, though epochal, wasn’t exactly heaven. Call her naive, but Lana Del Rey chooses positivity; she believes in the power of art and symbols. “Coachella” ends with a beautiful fade-out, ushering in Lust For Life’s shift from the personal to the political.

46. “Money Power Glory” (Ultraviolence, 2014)

On Born to Die, Lana sang about the fame and fortune she was on the verge of attaining. “Money Power Glory” takes that character and her ambitions to the extreme. In her sole collaboration with writer and producer Greg Kurstin, who provides the song’s heavy, dubby drums, Lana mourns the death of the old order, and proposes a new one: greed. “I want money, and all your power, all your glory/ Hallelujah, I wanna take you for all that you got,” goes the chorus -- high, spectacular, yet anything but triumphant.

“Dope and diamonds/ That’s all I am,” she repeats in the bridge, sounding utterly dejected. Lana’s past odes to materialism, like “National Anthem,” were usually sung with a knowing wink. “Money Power Glory” makes fame and wealth sound like an incurable hallucination.

45. “Dayglo Reflection” (Bobby Womack feat. Lana Del Rey, The Bravest Man in the Universe, 2012)

On legendary soul singer Bobby Womack’s final album, produced by Damon Albarn, Womack and Lana Del Rey trade musings about the infinite beauty within existence. Over stunning jazz piano chords, and offbeat drums sampled from a Captain Beefheart record, his weathered voice gives way to her smooth, silky tone, becoming as much her song as his. Lana’s first big collaboration with an established artist, “Dayglo Reflection” proved the depth of her musicianship, that she was far more than a flash in the pan. The trio’s only live performance, on French TV show Le Grand Journal, is riveting. Womack and Del Rey hold hands tightly throughout, willing the experience not to end.

44. “Pretty When You Cry” (Ultraviolence, 2014)

The most ragged gutter ballad on a raw album, “Pretty When You Cry” was written and improvised on the spot. Lana’s first take, her voice cracking and wounded, remains the core of the final recording. Blake Stranathan’s scuzzy, hypnotic guitars drag the song even further down, like Cat Power or the Velvet Underground at their lowest. “All those special times I spent with you, my love/ They don't mean shit compared to all your drugs/ But I don't really mind...” Lana knows her character’s fate is hopeless. All she can do is sing a paean to her own demise: “I’m pretty when I cry...”

43. “Sad Girl” (Ultraviolence, 2014)

On much of Ultraviolence, Lana plays a tragic, almost villainous figure. “Being a mistress on the side/ Might not appeal to fools like you,” she coos on “Sad Girl,” over fingerpicked blues guitar. Not mincing words, she you in on her secret -- she’s in denial. “His money on the side.../ Makes me a sad girl.../ I’m a bad girl,” she sings over and over. With its lush pianos and mellotrons, self-destruction has rarely sounded so beautiful.

42. “Get Free” (Lust For Life, 2017)

Lust For Life found Lana reassessing the role of her music, and what it means to the culture. On the album’s final track, she looks to the past. She quotes “Ride” directly, refuting the mindset she was once in: “Sometimes it feels like I’ve got a war in my mind/ I want to get off, but I keep ridin’ the ride.” She looks to the present, articulating her motivations behind the journey that started with “Love”: “This is my commitment/ My modern manifesto/ I’m doin’ it for all of us/ Who never got the chance.” And she opens another door for the future: “I wanna move/ Out of the black/ Into the blue…”

The song’s guitar chords (which do bear a passing resemblance to Radiohead’s “Creep”) are neither happy or sad, but open, undetermined. For that reason, “Get Free” is almost an anticlimactic track to end on. It’s not as buoyant as “Love,” as moving as “Change”... but as the song ends on sounds of crashing waves, you feel like you’re right there with Lana, ready to take the next step on a lifelong journey towards nirvana.

41. "Love song" (Norman Fucking Rockwell, 2019)

In its sonic palette -- muted piano chords, fluttering strings, subtle bass drops -- “Love song” might be the closest Lana’s come to replicating the sound of “Video Games,” with the entirely opposite emotional effect. “Love song” breaks no new lyrical ground for Lana, with its references to fast cars and party dresses, but she assembles those images into one of her most tender displays of romance. Time stands still as she sings, “Is it safe to just be who we are?/ Oh, be my once in a lifetime,” over an Antonoff production that feels like the summer sun through a car window.

Free from darkness, without a care in the world, it’s the kind of observational, low-stakes song she couldn’t have written on records past. Lana’s always aspired to turn her life into art, but she’s rarely found beauty in such ordinary moments, the way Norman Rockwell is remembered for painting America. “The taste, the touch, the way we love/ It all comes down to make the sound of our love song…”

40. “Not All Who Wander Are Lost” (Chemtrails Over the Country Club, 2021)

Named after a phrase borrowed from Tolkien, this is one of Lana’s sparsest songs -- somewhere between the whisper-close intimacy of Elliott Smith and the genteel country strains of Patsy Cline in the ’60s. Portraying a singer who lives on the road, she sings to a fellow wanderer who claims he’ll commit: “The thing about men like you is you got a lot to say/ But will you stay?” Though the verses feel modern, the titular chorus, sung with gorgeous countermelodies, has the feel of a folk spiritual passed down through the generations. Lana’s written the inverse of “Ride” -- a song where she stays on the move, yet just maybe, she’s already found peace inside herself.

39. “Dark But Just a Game” (Chemtrails Over the Country Club, 2021)

Written around a phrase Jack Antonoff said to her, “Dark But Just a Game” captures the duality of Lana Del Rey better than any song since “West Coast.” It feels like two songs in one: the minor-key, dubby verses where she muses on “the price of fame” -- how every tragic icon is eventually swallowed by their public image. By contrast, the choruses are major-key and folky, as she sings about herself: “The best ones lose their minds/ So I’m not gonna change/ I’ll stay the same.” She’s never before sung about Hollywood tragedy with such a light touch. The song is a little moral parable: whether or not you choose to gamble with fame, the artist that stays true to herself survives.

38. “Honeymoon” (Honeymoon, 2015)

In 2019, Honeymoon marks the midpoint of Lana Del Rey’s career; the calm after the storm of Born to Die and Ultraviolence. With its Bernard Herrmann-inspired film noir strings, “Honeymoon” sounds much darker than its title suggests, yet it's far more languorous than any of her previous work. This new Lana is no longer tormented by love, content to simply indulge her music in the concept of romance.

“Honeymoon” betrays little sense of desire -- over its six minutes, the song floats luxuriously in the air, gently building to a climax that never arrives. Though she invites us to join her -- “Our honeymoon/ Say you want me too” -- she’s never written a more mysterious, inscrutable song. Like a lounge jazz singer in purgatory, she sings on and on: “Dreaming away your life...”

37. “Doin’ Time” (Norman Fucking Rockwell, 2019)

It’s always been easy to dismiss Sublime as ’90s bros, but behind their Cali ska-punk image lay a confluence of dub, jazz, even rap-inflected songwriting. Lana makes just the slightest of changes to the '96 original -- she lowers the tempo, and her production is more atmospheric -- but she breathes a dizzying amount of new life into the song. It’s surreal to hear her sing lines like “Bradley’s on the microphone with Ras M.G.,” as if she’s channeling his ghost through her own artistic vision. “Doin’ Time” isn’t just a tribute to Sublime; with the benefit of hindsight, Lana’s able to be more generous with the song than the band were in their original lifetime.

36. “This Is What Makes Us Girls” (Born to Die, 2012)

Born to Die’s finale frames the album as a coming-of-age narrative. In the verses, Lana sings about getting into trouble as an adventurous teenager. But the chorus zooms out, like the ending montage of a film: “This is what makes us girls/ We don’t stick together ’cause we put love first/ Don’t cry about him.../ It’s all gonna happen!”

Where “Born to Die” opened the album with a romantic sense of doom, “This Is What Makes Us Girls” ends it with desperate hope, a plea for women to love themselves -- even if Lana’s narrator doesn’t know if she’ll ever really grow up. Born to Die wasn’t about wallowing in sadness, it was a generational statement -- a call for the listener to cry on Lana’s glamorous shoulder, and when the tears stop, to pick themselves back up and see how much they’ve grown.

35. “You Must Love Me” (Unmasked: The Platinum Collection, 2018)

In one recording, Lana covers two inspirations -- Andrew Lloyd Webber and Madonna -- in one fell swoop. “You Must Love Me” was written not for the original version of Evita, but its 1996 film adaptation. Madonna sings her version near the end of Eva Perón’s life; her voice is raw, desperate to be loved and remembered as an icon. In Lana’s version, recorded to commemorate Lloyd Webber’s 70th birthday, her vocal performance is smooth, unvarnished, yet no less affecting. Instead of demanding love, she gives unconditionally, with boundless emotional generosity. “You Must Love Me” is as pure an expression of romance as she’s ever recorded.

34. “Blue Jeans” (Born to Die, 2011)

As the much-anticipated follow-up to “Video Games,” “Blue Jeans” condensed a similar vein of melodrama into a more concise, yet equally strange pop song. The first track Lana recorded with Emile Haynie, who’d go on to define Born to Die’s sound, “Blue Jeans” combines a hodgepodge of classical strings, Twin Peaks guitar twang, stop-start hip-hop drums, and almost jarring vocal samples. Lana gives one of her most unhinged vocal performances, spitting the verses in her lower register; desperately pleading as the choruses escalate into a heart-pounding double-time bridge. “I will love you till the end of time/ I would wait a million years,” she sings, promising devotion to a lover even as a life of crime takes him away from her.

We’d never heard anything else quite like it in 2011, before Lana’s neo-noir visuals and hip-hop stylings trickled down to mainstream pop. Though she’s outgrown her early, regrettably named “gangster Nancy Sinatra” persona, she’s written few songs since that are as brazenly thrilling as “Blue Jeans.”

33. “High by the Beach” (Honeymoon, 2015)

Honeymoon’s first official single found Lana looking for an escape from the public’s prying eyes. She sounds terse, tired, yet relaxed all at once, as she sings about a peace she’s yet to find. “High by the Beach” slyly reinvents Born to Die’s sonic palette, but with none of the sturm und drang. Beneath jazzy, ambiguous organs and blippy synths lies a circular, muted trap beat -- a hip-hop facsimile of playing a drum kit with jazz brushes.

In one of her most recognizable videos, directed by Jake Nava, Lana finds refuge in a lavish beachside house, until a paparazzi helicopter intrudes… so she pulls a grenade launcher out of a guitar case, and shoots them out of the sky. It culminates in one of her definitive images, a still shot of her holding a gun: defiant, glamorous, remorseless. Don’t call her a celebrity -- she’s an artist.

32.  “Chemtrails Over the Country Club” (Chemtrails Over the Country Club, 2021)

The title track of Lana’s sixth album is an enigma wrapped in a mystery. On the surface, Lana’s protagonist sings sweetly about her everyday life in America: “We laugh about nothing as the summer gets cool/ It’s beautiful how this deep normality settles down over me.” Yet the song keeps coming back to its titular phrase -- those chemtrails an ever-present omen. Jack Antonoff’s waltz arrangement grows subtly darker with time, but there’s no payoff -- instead, the song drags on and on, slowly fading into a nearly minute-long drum outro. Much like “Video Games,” the song’s beauty feels unreal -- as if it’s all a distraction from some slow, inevitable, indefinable doom.

31. "Cinnamon Girl" (Norman Fucking Rockwell, 2019)

A sonic return to Honeymoon’s serene orchestral trap, this time with Antonoff at the helm. “Cinnamon Girl” is less a story than a sketch of a lover who causes Lana pain, but who she pledges to uplift: “All the pills that you take/ Violet, blue, green, red to keep me at arm’s length don’t work/ You try to push me out, but I just find my way back in…”

The song builds to a devastating, confessional chorus: “There’s things I wanna say to you, but I’ll just let you live/ Like if you hold me without hurting me/ You’ll be the first who ever did.” The more she repeats those words, the more affecting they become. Just as fascinating is a 90-second instrumental outro that plays out in several movements -- from strings to twinking piano to trap drums -- that dwells on the song’s beautiful, unresolved tension.

Songwriting isn’t just about what an artist says, but what they leave to the imagination. With so few words, Lana conjures an entire, unfulfilled romantic history in the listener’s mind, and shows how one gesture can begin to heal the future.

30. “God Knows I Tried” (Honeymoon, 2015)

One of a handful of waltzes in her catalogue, “God Knows I Tried” finds Lana retreating from public view. “I feel free when I see no one/ And nobody knows my name.../ I've got nothing much to live for/ Ever since I found my fame... ” After all she’s endured, she sounds weary, yet calm, knowing that little can faze her.

In her 2015 Billboard feature, novelist Bruce Wagner describes “God Knows I Tried” as “somewhere between The Beach Boys’ ‘God Only Knows’ and Leonard Cohen’s ‘Hallelujah’” -- lofty comparisons that her song truly earns. A timeless piece of religious, existential poetry, Lana leaves her ultimate fate to God. By 2015, the year she turned 30, she had little to prove as an artist except to herself. Whatever her reputation, she knows she did her best.

29. “Tulsa Jesus Freak” (Chemtrails over the Country Club, 2021)

On “Tulsa Jesus Freak,” Lana’s narrator dreams of leaving her lifestyle behind and returning to the Midwest with her man. Her love’s unreliable (“Keep that bottle at your hand, my man”) and they’ll be in the middle of nowhere (“Down in Arkansas the stores are all closed”), but Lana’s a desperate believer: “We’re white-hot forever/ And only God knows!” In the verses, there’s a subtle, eerie layer of Auto-Tune on her voice; in the choruses, tiny bits of Ultraviolence-style fuzz creep in over Antonoff’s muted trip-hop production. Nearly every other track on Chemtrails is a positive depiction of settling down -- so of course, Lana had to get in just one song that makes domesticity sound like being trapped in a dusty attic.

28. “The Other Woman” (Ultraviolence, 2014)

First recorded by Sarah Vaughan, but made iconic by Nina Simone, both singers delivered “The Other Woman” with a certain distance. They sang as an impartial observer, or perhaps the wife, telling a sad morality play of a beautiful, loveless mistress. But Lana steps into the other woman’s shoes, embracing the beauty of the melody, the lushness of her lounge jazz arrangement. There’s zero separation between herself and the character she’s playing. Her voice quivers as she sings the closing lines -- “And as the years go by/ The other woman will spend her life aloooone” -- as if they’re the last notes she’ll ever sing.

This is the same downtrodden figure of “Ride,” “Ultraviolence,” “Shades of Cool,” who devotes herself to older men who’ll never really love her back. She’s so trapped by two ideals, young and beautiful, that there’s nothing else to her. On Ultraviolence, love is the ultimate drug, true believers are addicts, and Lana Del Rey is their prophet. “The Other Woman” isn’t just the final track on the album; it essentially exorcises Lana’s mistress character for good. She’d never sing about herself in the same way again.

27. “Yayo” (Paradise, 2012)

On Paradise, “Yayo” feels distant, drenched in reverb, as Lana warbles over piano like a lounge singer. But the original acoustic guitar-led version, the most significant track on 2010’s Lana Del Ray a.k.a. Lizzy Grant, is so intimate that it’s almost too sad to listen to. “Yayo” paints a stark portrait of a toxic submissive relationship: “I need you like a baby when I hold you/ Like a druggie, like I told you.” Her situation feels completely hopeless, but she persists with the charade: “Let me put on a show for you, daddy...” As the song ends, it feels like a beautiful death rattle. In either version, “Yayo” could be the most tragic song Lana’s ever written.

26. “Summertime Sadness” (Born to Die, 2012)

“Summertime Sadness” isn’t the most grand or moving song on Born to Die, but it is the most accessible. Lana’s lyrics are fueled by desire, but unlike many of her early songs, there’s no literal sense of tragedy: “Got my bad baby by my heavenly side/ I know if I go, I'll die happy tonight!” The phrase “summertime sadness” is seasonal -- it suggests a fever, a temporary affliction, a young love that knows it’s fleeting. Glamorous, romantic, but not overwhelmingly sad, the music video was a perfect realization of early Instagram culture -- think girls in flower crowns at music festivals, shot through nostalgic, analog-style camera filters.

Initially Born to Die’s fourth single, it wasn’t until 2013 that the Cedric Gervais remix made Lana the unlikeliest of mainstream pop stars. His version is hardly subtle, though it’s not as hammer-blunt as much of pop or EDM at the time. Even in a different sonic landscape, over electro-house synths and 4/4 kick drums, Lana’s distinct vocals don’t lose their personality. Though Gervais’ version was a bigger crossover hit at the time, it ultimately feels like it exists in an alternate universe -- Lana hadn’t heard the remix until it was on the radio, and has never shown any affection for it in interviews. The original remains the definitive version. It’s far more representative of Lana’s musical sensibilities, and in one of the first signs of her reach within popular culture, even inspired a Bangerz-era Miley Cyrus cover.

Either way, “Summertime Sadness” wasn’t all that provocative, and didn’t inspire furious debates about Lana’s authenticity -- it was just a great pop song. Between the original and the remix, it’s still her highest-performing single to date, reaching No. 6 on the Billboard Hot 100 in September 2013.

25. “Freak” (Honeymoon, 2015)

Is it ironic that one of our greatest modern California mythologizers is an east coast native? But that’s exactly it -- the Californian dream, from the Wild West to Coachella, has always been a dream of escape and rebirth. Whether or not that’s attainable is anyone’s guess -- including Lana’s. “Looking back, my past/ It all seems stranger than a stranger,” she sings, before inviting you to leave it all behind, and cleanse yourself with her in the Pacific Ocean. The song’s production is an odd, alluring mix of trap 808s, 1940s noir brass, and layers of disembodied backing vocals, voices inside her head. It’s as if Lana’s seduced herself into believing, too -- she’s rarely gotten so high on her own mythology.

The video, the first since 2012 to be directed by Lana herself, casts Father John Misty as a guru-like figure surrounded by young women who take acid and literally drink Kool-Aid. We see no death, but there is an afterlife -- a five-minute extended coda of blissfully slow footage of Lana and friends frolicking underwater, set to Claude Debussy’s “Clair de Lune.” It may be the purest image of beauty she’s ever created.

24. “Change” (Lust For Life, 2017)

“Change” carries the weight of Lana’s personal growth, after all she’d been through. Rick Nowels’ muted, flowing piano arpeggios embody her thoughts, as the specter of war hangs over her. “There’s somethin’ in the wind, I can feel it blowin’ in/ It’s comin’ in softly on the wings of a bomb…” Her voice wounded, hesitant, Lana wonders if anything she does matters. “Lately, I’ve been thinkin’ it's just someone else's job to care/ Who am I to sympathize when no one gave a damn?”

But as the song progresses, modulating to a major key, she becomes more resolute, as if she’s emerging from a fog. In the pre-chorus, she names a new mantra, four words she aspires to: “honest, capable.../ beautiful, stable.” There’ll always be sadness in Lana’s music, and in life, but by 2017, she was past romanticizing her feelings of self-destruction. The song’s ultimate message is that uncertainty is okay -- it’s a fact of life. In a serendipitous moment, “Change” was recorded the night before Lust For Life was to be submitted to the label. The album wouldn’t feel complete without it.

23. “Love” (Lust For Life, 2017)

Amidst the turmoil of early 2017, Lana Del Rey did the unthinkable: she wrote a song with no darkness, no contradictions, just love. Somehow, she conjured her album’s unlikely first single from familiar elements: ’60s girl group melodies, booming Phil Spector-style drums, and the most common chord progression in pop music. She wasn’t just singing for herself, or for the sake of nostalgia -- she was singing for the next generation. “Look at you, kids, you know you're the coolest/ The world is yours and you can’t refuse it.../ It’s enough, to be young and in love...” In the most shocking move of all, in the music video and the album cover, Lana actually smiles. She’s not totally unburdened -- “It’s enough just to make you feel crazy, crazy, crazy...” but it’s a start. It would be so, so easy to call “Love” naive, but after so long, it felt just right.

22.  “For Free” (feat. Zella Day & Weyes Blood, Chemtrails Over the Country Club, 2021)

Chemtrails is Lana’s third album to end with a cover -- this time of Joni Mitchell, from her foundational 1970 album Ladies of the Canyon. Where Joni’s original recording is just solo piano and voice, youthful and uncertain, Lana’s cover is more indulgent, sung with more tenderness to herself. Alongside her peers and tourmates, the indie pop-turned-folk singer Zella Day and the baroque-pop prodigy Natalie Mering, a.k.a. Weyes Blood, Lana uses Joni’s words to muse on their own lives. They acknowledge their success -- “I play for fortunes/ And those velvet curtain calls” -- but watching a man on the street, playing his clarinet for free, they can’t help but feel a twinge of envy. In the 51 years since Joni wrote “For Free,” so much has changed -- yet the core human questions we grapple with, in life and art, are the same. All Lana Del Rey can wish for is a career like Joni’s -- successful, beloved, entirely her own person… to dance till she dies, and look back with no regrets.

21. “Old Money” (Ultraviolence, 2014)

On Ultraviolence’s penultimate track, the druggy haze fades away. Soundtracked by lush piano and strings, Lana sounds clear-eyed, lucid, as she recalls a time when her world seemed idyllic. “Old Money” is the most grounded version of Lana’s creation myth, one where she has loving parents and a stable upbringing, but still has to leave her Eden in search of fulfilment. “My father’s love was always strong/ My mother’s glamour lives on and on/ Yet still inside, I felt alone/ For reasons unknown to me...”

We’re all shaped by our experiences, but sometimes nothing can explain what compels our direction in life. Much of Ultraviolence is about the unavoidable call of addiction, how our brain chemistry determines our fate. But with “Old Money,” Lana shows us that there is love in our past; that we can always go home, at least in our memories. “And if you call for me, you know I’ll run/ I’ll run to you…”

20. “Terrence Loves You” (Honeymoon, 2015)

The crown jewel of Honeymoon, and Lana’s own favorite song from the album. As she mourns a lover -- dead or gone, it feels the same -- she finds solace in her art: “I lost myself when I lost you/ But I still got jazz when I’ve got those blues...” With its glimpses of fluttering strings and saxophone, “Terrence Loves You” is her jazziest song, and perhaps her most timeless -- it feels like it could have been recorded in the 1930s. “Terrence” epitomizes Honeymoon: an album where Lana allows herself to feel her sadness, but is never overwhelmed by it; where there’s a distant light at the end of the tunnel, if you allow yourself the resilience to get there.

19. “Wild at Heart” (Chemtrails over the Country Club, 2021)

Lana Del Rey has always fantasized about two things: unconditional love, and leaving her stardom behind. Combine the two, and you get an instant classic. She’s never sounded half as carefree as she does on “Wild at Heart,” singing over the warmest, most ’70s soft-rock instrumental of her career. The words are familiar, but the beauty’s in the details: the cute, knowingly silly lyrics like “I love you lots like polka dots/ You’re killing me more/ Than coffee pots and Insta-thots.” It’s the way her voice flutters in the pre-chorus, the rare downward key change into the chorus with her leisurely double-tracked vocals, and the bridge -- stacked with more vocal harmonies than we’ve ever heard on a Lana song. “Wild at Heart” is simple and life-affirming, a song it's impossible to imagine her writing even four years prior.

18. “Off to the Races” (Born to Die, 2011)

When it premiered on the iTunes Store in late December 2011, “Off to the Races” came as quite the curveball. Whatever “Video Games” and “Blue Jeans” seemed to presage, it wasn’t a song as wordy and offbeat and campy as this. On first listen, Lana’s lyrics seem like a mishmash of conflicting images: “God, I’m so crazy, baby/ I’m sorry that I’m misbehaving/ I’m your little harlot, starlet/ Queen of Coney Island...”

To add to the stylistic disorientation, she delivers her vocal with a jazz singer’s intonation, a rapper’s cadence, and even slips into a Betty Boop-like squeak, all over clattering beats. “Off to the Races” floods you with unapologetically feminine cliches, so overwhelming that it feels hyper-real. Lana could have made a career out of aggressively weird songs like this, but there’s only one “Off to the Races,” and that’s perfect.

17. “13 Beaches” (Lust For Life, 2017)

Critics have often described Lana’s songs as trip-hop, a label that usually comes off as reductive. But “13 Beaches” finally takes Lana to full Massive Attack territory, with wind-swept strings, and sampled drums straight out of “Teardrop,” and the results are glorious. The song was inspired by a real-life experience, where Lana spent a day trawling through the California coastline to find one beach without paparazzi or onlookers.

The lyrics echo “High by the Beach,” but this version of Lana is more mature. She knows that she’s looking for an escape, and that she can’t outrun her memories. Each line of the chorus brings a new confession: “It hurts to love you, but I still love you/ It’s just the way I feel.../ And that I’ve been dyin’/ For something real.” She acknowledges her pain, but more than that, she sounds determined to survive. The beach grants her the serenity to confront her demons: “Can I let go, and let your memory dance/ In the ballroom of my mind?”

16. “Ultraviolence” (Ultraviolence, 2014)

It can be hard to tell how literally we should take a Lana Del Rey song, but “Ultraviolence” seems to be chillingly autobiographical. A somber ballad, Lana sings from the perspective of a woman who’s rationalizing the domestic abuse she’s going through. She croons with an unnerving tenderness, reliving her emotional turnoil in the moment. “I’m your jazz singer and you’re my cult leader/ I love you forever,” she speaks in the bridge, alluding to a real experience she had in an “underground sect.” These are themes that most would consider too heavy for a pop song -- but this was the title track and third single of an album that debuted atop the Billboard 200.

But “Ultraviolence” is far from the first to explore such territory. The lyrics reference two equally disturbing pop-art predecessors: “He Hit Me (It Felt Like a Kiss),” the 1962 Crystals single co-written by the now-infamous Phil Spector; and A Clockwork Orange, the disturbing, satirical book and film that coined the term “ultraviolence.” Violence in art is rarely mundane; it’s brutal and spectacular -- because what’s the point in enduring pain if it can’t be turned into something meaningful? Ultraviolence depicts beauty and tragedy in equal measure -- each deepening the other’s grip on us, the listener.

15. “Norman fucking Rockwell” (Norman Fucking Rockwell, 2019)

Lana’s fifth album opens with lush brass, strings, and Randy Newman-like piano. And then, an all-time opening line: “Goddamn man-child/ You fucked me so good that I almost said, ‘I love you!’” Once upon a time, we thought of Lana as an eternal sad-girl, a Morrissey-esque moper. But here, she turns her sweet venom on those who would box her in -- “Your head in your hands/ As you color me blue.”

The man in this song is her mirror image; a mediocre artist defined by his self-loathing masculinity, who refuses to evolve with the times -- “Your poetry’s bad and you blame the news/ But I can’t change that, and I can’t change your mood.” “Norman fucking Rockwell” interrogates the concept of sadness, but Lana herself is far from blue -- she’s made it out to the other side, triumphant. The song ends on the oceanic sounds of brass, as if beckoning you to sail away on a great voyage…

14. “Cruel World” (Ultraviolence, 2014)

“Cruel World” opens Ultraviolence by pulling us into a completely different sonic world. Over nearly seven minutes, Lana sifts through the wreckage of a relationship. “Shared my body and my mind with you/ That’s all over now.../ I’m finally happy now that you’re gone.” Dan Auerbach’s guitars chime beneath her, until the chorus erupts into distortion, pulling her violently back to a past that still haunts her: “You dance in circles around me/ You’re fucking crazy.../ You’re crazy for me.”

While Born to Die and Paradise expanded the scope of mainstream pop, Ultraviolence could be the most aggressively uncommercial “pop” album of its decade. Gone are the Hollywood references, the cinematic hip-hop production -- this is the blues, spiritual and guttural and painfully honest. As the song ends with her wails, Lana Del Rey is ready to burn down everything you thought you knew about her. Things would never be the same.

13. “National Anthem” (Born to Die, 2012)

“Money is the reason we exist/ Everybody knows it, it's a fact/ Kiss kiss!” The fifth and final single from Born to Die is a playful take on love as materialism, with a dark underbelly. In the verses, Lana plays fast and loose with syllables and rhymes: “I sing the national anthem/ While I’m standing over your body, hold you like a python.” Some thought it was creative, others irritating, but she’d found a way to internalize hip-hop’s rhythms and attitude like few white female pop stars before her. The chorus finds Lana at her most celebratory, but the bridge is more sinister: “It’s a love story for the new age… Overdose and dying/ On our drugs, and our love, and our dreams, and our rage/ Blurring the lines between real and the fake.” What if all this glamor and wealth only masks a deeper emptiness? Lana knows, but she doesn’t care -- she’ll buy in anyway.

It’s impossible to hear the song without thinking of the epic music video, which cast Lana as both Marilyn Monroe and Jackie Kennedy, and A$AP Rocky as JFK. More than simple ’60s cosplay, it was a star-making performance for both artists. “National Anthem” presented itself as not just an alternate vision of American history, but an alternative to the brash mainstream pop of the early 2010s. With virtually no radio airplay, Lana played the role of usurper, fashioning herself as an icon through YouTube and the press -- and it worked. “National Anthem” was her first song that people had to dissect as an event, that was too big to be dismissed outright. Though she’d steer away from such pop grandeur in the years to come, “National Anthem” helped enthrone her as a pop star for life.

12. “West Coast” (Ultraviolence, 2014)

The first glimpse of Lana Del Rey’s sophomore album, “West Coast” radically reimagined what a Lana Del Rey song could sound like -- not once, not twice, but three times over. First, those verses -- her voice unusually hushed, driven by gentle guitar brushstrokes and restless, skittering drums. Her voice rises, “your love, your love, your looove,” as the verse grinds to a halt. A guitar twangs, and the chorus crawls into a deeper state of consciousness, twisting the song into an entirely new configuration: Lana’s vocal harmonies float above Dan Auerbach’s shuffling “narco-swing” instrumentation.

“West Coast” is an astonishing pop record because it breaks the rules of mainstream pop, going to territory only Lana could walk. Even with little radio promotion, it remains her second highest-charting single, debuting in the top 20 of the Hot 100 -- which shows just how central a figure she was to mid-’10s pop. It’s her contribution to a century of California mythology, channeling everything from Chinatown to The Doors to even Dr. Dre, as a high G-funk synth infiltrates the song’s final chorus. “Down on the west coast, they got their icons,” she sings, willing herself to become one too.

“West Coast” feels less like a song that someone wrote than a recording that materialized from the hazy Pacific air with a mind of its own. But what about the song’s third reimagination? Its radio mix turns it into a jaunty ’70s soft rock jam worthy of Fleetwood Mac. Even stripped of all its darkness, “West Coast” is mesmerizing.

11. “Young and Beautiful” (Music from Baz Luhrmann’s Film The Great Gatsby, 2013) 

“Young and Beautiful” is not simply about youth or beauty. It’s a desperate, existential plea by someone who doesn’t want to burn out, but is terrified of fading away. “I’ve seen the world, done it all/ Had my cake now…” In the chorus, she asks over and over, “Will you still love me when I’m no longer young and beautiful?” She can only answer herself -- “I know you will, I know you will, I know that you will…” “Young and Beautiful” remains the height of Lana’s work with melodic pop songsmith Rick Nowels, who’s since become her longest-tenured collaborator. His production, with its cavernous, chamber pop strings, is breathtaking -- and the arguably superior Dan Heath orchestral version, used in the music video, is even more immersive.

There’s just one exception -- a bridge that awkwardly takes the song out of its classic Hollywood setting. “All that face makes me wanna party!” Even so, that made it a perfect theme for Baz Luhrmann’s gaudy, yet subversive The Great Gatsby. Both the film and F. Scott Fitzgerald’s novel are about glittery surfaces that mask desperate, empty cores. There’s the faintest hint of knowing narcissism in “Young and Beautiful,” a buried irony that most pop singers would run from. Fittingly, Lana performed it at Kim and Kanye’s Versailles wedding -- an iconic pop culture moment that none of the general public have actually seen.

The music video, directed by Chris Sweeney and Sophie Muller, lets you imagine. Lana’s never looked more glamorous, made up like Rita Hayworth in Gilda; singing to an orchestra in silhouette, evoking Fantasia. It’s her “Vogue,” the moment she ascended to the level of movie-star icon in the popular consciousness. “Young and Beautiful” remains one of Lana’s biggest pop crossover hits, and one of her most timeless songs. Youth and beauty are fleeting, but the fear of loneliness is eternal.

10. “Shades of Cool” (Ultraviolence, 2014)

Ultraviolence’s second single is a soulful, slow-burning waltz that pays tribute to two of Lana’s muses: music and men. In the moody verses, she idolizes her lover -- “My baby lives in shades of blue/ Blue eyes and jazz and attitude.” In the chorus, her voice soars instead, but her words mourn his unfixable, “unbreakable” heart. His cool, stoic nature draws her to him, yet it keeps them distant, trapped in an illusion of love, without intimacy. Lana’s voice flutters and weaves around Dan Auerbach’s guitars; she’s never given a more expressive vocal performance about a more unknowable man. Art, like love, is supposed to illuminate human nature, but some things are impossible to define. As she vamps over the outro, she ends the song with a drawn-out moan -- a wordless sigh, resigned to her fate.

9. “White Dress” (Chemtrails over the Country Club, 2021)

Lana Del Rey opens her sixth LP by walking us through her formative memories. Over an ambiguous piano melody, she sings, quiet and airy, “Thinking of a simpler time…” In each chorus, her voice jumps into a loud, breathy whisper, recalling, “I was a waitress working the night shift.../ Down at the men in music business conference/ Down in Orlando, I was only nineteen!” She sounds awed, as if even now, she can’t believe how she felt at the time: “I only mention it ’cause it was such a scene/ And I felt seen.../ Look how I got this!”

“White Dress” feels like a stream of air, a current pulling you back into the past. Jack Antonoff plays every instrument -- piano, guitar, brushes on drums -- with a flowing, impressionistic touch, as if channeling Miles Davis’ band on Kind of Blue. It’s jazz -- it’s open-ended. 

As the song builds to a climax, Lana confesses, “It made me feel, made me feel like a god/ It kinda makes me feel, like maybe I was better off…” She can’t exactly explain that spark of inspiration -- only that there was magic in the ordinary that night. She doesn’t even tell us the complete story; like a dream, the song barely begins or ends.

“White Dress” is the forever quandary of Lana Del Rey, the eternal contrarian. When she was Lizzy Grant, she dreamed of being famous. As soon as she became Lana Del Rey, she dreamed of losing it and becoming an underdog again. Like a Mobius strip, she’ll never stop questioning that core impulse -- yet every version she’s written of this narrative is the same. She never changes her mind.

8. “Mariners Apartment Complex” (Norman Fucking Rockwell, 2018)

“You took my sadness out of context/ At the Mariners Apartment Complex/ I ain’t no candle in the wind…” Her voice quavers as she looks back on her life, who she’s become, and what she stands for. Co-written and produced by Jack Antonoff, our first glimpse of Norman Fucking Rockwell has a sonic palette unlike either of their past work: dry, intimate Laurel Canyon folk, almost completely free of reverb.

But the chorus blossoms, stacking strings on mellotrons on piano: “You’re lost at sea, then I’ll command your boat to me again…” Until the instruments suddenly subside, like a retreating wave: “Right where you are, that’s where I am/ I’m your man.” Invoking the great Leonard Cohen, Lana Del Rey reboots her image once again -- this time as a generational balladeer; a beacon of strength in any weather. Weep on her shoulder, and her embrace will be gentle.

7. “Born to Die” (Born to Die, 2011)

When “Video Games” went viral, Lana Del Rey was pegged as the next big female indie singer-songwriter, someone who wrote poetic character studies about women and love. But no, Lana wanted to be a new kind of pop star, one who wrote songs for swaying American flags, chapel ceilings, queens on their throne. “Video Games” made her, but “Born to Die” declared her ambitions. The song is a morbid, anthemic death pact, the kind that could only be written by a 26-year-old with a self-proclaimed old soul. Over Emile Haynie’s grandest production lies Lana’s vocal -- unusually intimate, as if she’s singing directly to you.

“Come and take a walk on the wild side/ Let me kiss you hard in the pouring rain,” she sang, inviting her true believers into a new world; a music video where Lana plays both conquering queen and biker girlfriend. As she suffers through a car wreck, flames, and a bloody, beautiful death, she creates a new persona: Lana Del Rey the martyr, an icon of feminine suffering, who would endure the most controversy-ridden press cycle of any new artist this decade, and emerge with her artistic reputation intact.

When it was released at the very end of 2011, the year we celebrated Born This Way and “apocalypse pop,” “Born” seemed jarringly depressive. To many, Lana Del Rey was edgy sad-girl provocation without substance. But “Born to Die” has endured because Lana dared to swing for the fences. She was years ahead of the game, giving voice to a sense of romantic fatalism we didn’t even know we had. The influence of both song and album can still be felt; now, in August 2019, the latter has spent over 300 weeks on the Billboard 200. But back when it first came out, the expectations seemed impossibly high. When you call your debut album Born to Die, where can you possibly go from there?

6. “The greatest” (Norman Fucking Rockwell, 2019)

“The greatest” opens with a piano and guitar chord progression that’s distinctly Elton John, as if it’s a comforting song you’ve heard a million times before. And yet, its lyrics are anything but -- referencing political anxieties, climate change, even nuclear war. What comfort can any artist offer in the face of such existential threats? “And I’m wasted.../ I’m facing the greatest/ The greatest loss of them all.” Lana can’t even seek refuge in her memories: “I miss New York and I miss the music/ Me and my friends, we miss rock ‘n’ roll/ I want shit to feel just like it used to.”

Even while singing some of the most delicate melodies she or Jack Antonoff have ever written, you can hear her voice fighting the urge to sink back into her old fatalism. “The greatest” name-checks two fallen American icons -- Dennis Wilson and Kanye West, an inspiration and a peer -- but more than that, the song’s about the fall of the concept of America the Beautiful itself. Was it always an illusion? Lana can offer no consolation, only a prolonged goodbye, concluding the song on a nearly two-minute outro, until she finally runs out of words to say.

Near the end of the video, where she sings and frolicks in docks and old bars, she symbolically puts her microphone back on its stand. “If this is it, I’m signing off...” Lana sings with such grace, like the musicians on the sinking Titanic, that you can’t help but feel grateful you were around to witness the end, if this is indeed it.

5. “Venice Bitch” (Norman Fucking Rockwell, 2018)

“Venice Bitch” feels like a lifetime in nine and a half minutes. It begins like many of Lana’s documents of a relationship, over soft guitar chords: “You write, I tour, we make it work/ You’re beautiful and I’m insane/ We’re American made…”

But after two choruses and a bridge, the point where most pop songs begin to look to the end, the song begins to unspool in time, as if it’s lost its own thread. Lana’s voice disappears for long stretches, as Jack Antonoff’s soundscapes grow more and more psychedelic, with analog synth noodling, “Maggot Brain” guitar feedback… “Venice Bitch” is like watching a garden grow in fast-forward, blooming and shedding its leaves with the seasons.

Lana’s once-idyllic relationship ebbs and flows forever, never settling, subject only to the sands of time. You expect a different outcome each time, but the song always plays out the same way. “If you weren’t mine, I’d be jealous of your love,” repeats Lana, concluding a song that might last nine minutes, or nine hours -- the more you listen to it, the more the moment slips through your fingers.

4. “Ride” (Paradise, 2012)

Far sooner than anyone expected, just eight months after Born to Die, Lana Del Rey returned with an entirely new single. Her only song produced by Rick Rubin, “Ride” was a mission statement, and an expansion on the themes of her still-fresh debut. Over even grander strings than usual, she sings in a warbling Roy Orbison vibrato: “I’ve been out on that open road.../ Singing blues has been getting old...”

“Ride” was a different kind of melodrama than she’d given us before -- it’s earthier, backed by live instruments, with a country-music soul. The song builds to a bridge where her voice -- nervy, desperate -- jumps up an octave: “I’m tired of feeling like I’m fucking crazy/ I’m tired of driving ’til I see stars in my eyes/ All I’ve got to keep myself sane, baby/ So I just ride, I just ride…” She has no choice but to accept her fate. The song’s five minutes feel like they could go on forever.

In the 10-minute video, directed by Anthony Mandler, Lana casts herself in her own Easy Rider fantasy. She plays a sex worker who moonlights as a singer, living a mundane existence, until she hooks up with a nomadic biker gang -- the only people in her world who seem truly free. Whether she’s seducing older men or pointing a gun to her head, her performance is so committed that it removes all doubt as to who Lana Del Rey truly is. She’s always blurred the lines between art and real life, but “Ride” obliterates them. This was her raison d’etre -- to make art, to be herself forever, whatever the cost.

In the epilogue, she speaks her truth: “Who are you? Are you in touch with all of your darkest fantasies? Have you created a life for yourself where you can experience them?... I have. I am fucking crazy... But I am free.”

3. “Brooklyn Baby” (Ultraviolence, 2014)

“Brooklyn Baby” has long been pegged as a satire of New York hipsters, but it’s always been so much more. Over gentle guitar strums and a booming, circular drum pattern, Lana paints a picture of her ideal partnership, one that’s founded upon art and romance alike: “Well, my boyfriend’s in a band/ He plays guitar while I sing Lou Reed/ I’ve got feathers in my hair/ I get down to Beat poetry…”

By 2014, Lana was already emerging as an artist in the countercultural tradition of Reed, Dylan, Joni Mitchell -- one who could sing faintly ridiculous lines like “I’m talkin’ ’bout my generation,” and “I’m churning out novels like/ Beat poetry on amphetamines,” and really mean them. If “Brooklyn Baby” is self-deprecating -- and with Lana, it’s often hard to tell -- it’s only done so with love. In a twist of cosmic irony, Lou Reed himself was supposed to contribute backing vocals on the song, but died the same day he was scheduled to record. As powerful as it would have been, the song loses nothing for it.

In the heart-stoppingly beautiful bridge, the drums drop out, and Lana pairs a divine melody with her most cutting lyrics: “You never liked the way I said it/ If you don’t get it, then forget it/ ’Cause I don’t have to fucking explain it.” It marks the first time that Lana liberated herself from her fraught public image. “Brooklyn Baby” is a shining light in the murky darkness of Ultraviolence; the first of her many devotionals to a life spent pursuing art and beauty.

2. “Video Games” (Born to Die, 2011)

“Video Games” is like being overwhelmed with feeling, and bored sick at the same time. It’s emotionally terrifying, yet irresistible -- and as improbable a breakthrough single as there’s ever been. On paper, Lana’s words make her relationship sound perfect, but her voice says otherwise.

“Video Games” builds slowly, with a disorienting mix of piano, synthetic strings and harps, and a snare drum that beats with the oncoming dread of a horror film. “It’s you, it’s you, it’s all for you/ Everything I do/ I tell you all the time/ Heaven is a place on earth with you,” she sings, pledging her devotion, with a barely detectable hint of knowing irony. Few have ever made domestic bliss sound so strange, yet uncomfortably familiar; trapped by the kind of love that we’re told should be “till death do us part.”

Lana’s self-directed video, first uploaded in July 2011, looked like the inside of her mind: a collage of idyllic home video footage, voyeuristic paparazzi shots, and Los Angeles landmarks, ending on a faded, distant shot of the Hollywood sign. It was as if Lana’s nostalgia for America past had been corrupted into a harsh, digital-camera reality, made all the more sinister by its soundtrack. "Video Games” was the product of a post-millennial pop culture that had recently lost its innocence all over again, after witnessing Britney Spears’ and Kanye West’s personal troubles, in the immediate wake of Amy Winehouse’s death… and yet, the video could only have been produced by someone who still wanted a slice of that Hollywood myth for herself. Lana cast herself as both auteur and lead actress, playing the part so well that many viewers couldn’t tell if she was self-aware. Either way, her fascinatingly blank expressions suggested she knew more than she was letting on.

When Lana Del Rey was a nobody, “Video Games” was so potent that its viral success felt like an act of fate. As it reached cultural consciousness, we tried to dissect, demystify, deny its hold upon us... yet an entire year of frenzied online debates, intense media scrutiny, and a contentious Saturday Night Live performance couldn’t dull the song’s power. Listening to it now, it’s become even more moving, ever since it’s been widely acknowledged as one of the best songs of the decade. “Video Games” feels lost in time, like a beautiful nightmare from which you might never want to wake.

1. “hope is a dangerous thing for a woman like me to have - but i have it” (Norman Fucking Rockwell, 2019)

How does it feel to be Lana Del Rey in 2019? To have lived your whole life under a different name, playing music to no one, then the next eight years in the public eye? She’s spent reinvention after reinvention clawing her way towards artistic and personal contentment -- so why is the closing track of Norman Fucking Rockwell so emotionally devastating?

In a room so empty you can hear the silence, she sits, almost alone, with her thoughts. As Jack Antonoff plays a muted piano waltz, echoing her every gesture, Lana looks back on her art: “I had fifteen-year dances/ Church basement romances, yeah I’ve cried/ Spilling my guts with the Bowery Bums is the only love I’ve ever known/ Except for the stage, which I also call home, when I’m not.” Even in this calm after the storm, the past still weighs on her, leaving her shaken in the present. She’s seen things in Hollywood, that maker of dreams, that silenced her from speaking up: “Hope is a dangerous thing for a woman with my past…” The future is uncertain, and her mind and body might still fail her: “There’s a new revolution, a loud evolution that I saw.../ A modern-day woman with a weak constitution, ’cause I’ve got/ Monsters still under my bed that I could never fight off.”

“I’ve been tearing around in my fucking nightgown/ 24/7 Sylvia Plath,” sings Lana, invoking the poet who wrote and died young by her self-destructive impulses. When trauma provides a well of inspiration, artists are forced to constantly relive their most intimate moments, commodifying themselves to make a living. “Shaking my ass is the only thing that’s got this black narcissist off my back…”

“Video Games” was so powerful that nearly a decade later, it still defines the way we see Lana Del Rey. For years, she was viewed as the queen of misery, both in song and public persona, even long after she thought she’d moved on from those early fixations: “Writing in blood on the walls/ ’Cause the ink in my pen don’t work in my notepad.” Perhaps in response, she gave combative, elusive interviews about wanting to throw it all away.

Many of her greatest works felt like her final proclamation, songs so dramatic and fatalistic she might never be able to top them: “Born to Die,” “Ride,” “Cruel World,” “The Other Woman,” “God Knows I Tried,” the “High by the Beach” video, “Swan Song." It was a form of control, the tantalizing prospect that Lana could culminate her career in a tragedy of her own making; the musical equivalent of the “Born to Die” video’s fiery car wreck. She even recorded an entire album, Ultraviolence, that probably should have killed her commercial prospects, but backfired miraculously. Like no other pop star this decade, Lana Del Rey wanted to define herself on her own terms, or not at all.

The truth is, sadness was never the purpose of her music. It was that beauty without suffering used to feel cheap, dishonest: “All of these debutantes/ Smiling for miles in pink dresses and high heels on white yachts/ But I’m not, baby I’m not...” Through Honeymoon, Lust For Life, and now Norman Fucking Rockwell, Lana Del Rey learned to write from a place of compassion for herself; to be a role model for her listeners, while allowing her past to amplify her newfound optimism. It was never about nostalgia, lovers, or breakups; she’s proven that she was her own muse all along. But still, the process of grieving, learning, and growing never ends, in life or art.

“Don’t ask if I’m happy, you know that I’m not/ But at best, I can say I’m not sad...” After eight years, for five and a half minutes, Lana drags you through heartbreak and back, all to earn one final stanza. Her voice quavers as she jumps up an octave -- whispering, gasping: “Hope is a dangerous thing for a woman like me to have – but I have it/ Yeah, I have it/ Yeah, I have it/ I have...” It’s the quietest, most vulnerable moment in Lana Del Rey’s discography, and the most truthful. Her future is unwritten, but she’ll write it with hope.