Taylor Swift‘s upcoming 52-date The Eras Tour, set to finally launch this Friday (March 17), is quite simply one of the most-anticipated (and most in-demand) tours in the history of American popular music.
There’s a number of reasons for that: For one, it comes at the very peak of Swift’s popularity, with the superstar singer-songwriter just experiencing the best first-week numbers of her career for last October’s Midnights album, and spawning her longest-running Billboard Hot 100 No. 1 hit to date in its lead single “Anti-Hero.” For another, it comes after the longest road layoff of Swift’s illustrious touring career, with nearly five years — as well as six (!!) Swift full-length releases, and one global pandemic — having transpired since the Reputation Stadium Tour kicked off in May 2018.
But perhaps the biggest reason is that Swift now has a 17-year song catalog that’s the rival of any artist this century — and maybe even further back — which she plans on revisiting at length in the career-spanning tour. Swift’s career has now taken her all the way from wide-eyed teenage fairytales to 30-something late-night anxiety attacks, from country-folk ditties to moody synth-pop soundscapes, from the commercial peak of iTunes to the apex of the streaming age, from a time when she was defined by her radio smashes to a moment when her albums don’t even need conventional hit singles to earn rave reviews, win Grammys, and generally dominate the culture. And throughout the ups and downs of her career, her signature strength has remained her songwriting — a peerless ability to make the personal universal and the intimate massive, which has now inspired multiple generations of future stars, changing the course of pop music in the process.
So this week, we here at Billboard wanted to take a moment to look back at our favorites from the now hundreds of songs that make up her singular discography. Below are our 100 favorites: the delicate, the enchanted, the borderline-treacherous, and everything in between. Check it out below, and (hopefully) see you at the Eras Tour: It’s been waiting for us, and we’re ready for it.
"Look What You Made Me Do" (Reputation, 2017)
Why It’s Era-Defining: Sure, “Look What You Made Me Do” is polarizing — there’s a reason it’s No. 100 on this list — but you can bet every fan who calls themself a Swiftie remembers where they were when the music video for the Reputation lead single dropped. With help from a perfectly campy Right Said Fred interpolation, the superstar came back from the #TaylorSwiftIsOverParty stronger than ever and expertly yanked back the narrative that had been taken from her.
Most Taylor Lyric: “But I got smarter/ I got harder in the knick of time/ Honey, I rose up from the dead/ I do it all the time/ I’ve got a list of names/ And yours is in red, underlined”
Fun Fact: In 2020, an ominous cover of the song appeared out of thin air in the opening credits of an episode of Killing Eve. Only when it was released on streaming platforms did Swifties discover the cover was by a mysterious new band called Jack Leopards and the Dolphin Club, and produced by Jack Antonoff and one Nils Sjöberg. — GLENN ROWLEY
"Forever and Always" (Fearless, 2008)
Why It’s Era-Defining: The scathing ode to teenage heartbreak came amid Swift’s string of famous heartthrob boyfriends, whom she’d later write songs about. Given the Jonas Brothers mania back in 2009, a breakup song potentially about Joe Jonas was the talk of the town.
Most Taylor Lyric: “I hold onto the night you looked me in the eye and told me you loved me / Were you just kidding?”
Taylor on Taylor: “I just figure if guys don’t want me to write bad songs about them, then they shouldn’t do bad things.” (Bonus note: Swift would play that Hoda Kotb interview clip back in her Fearless tour days before stepping onstage to perform this one.) — RANIA ANIFTOS
"Dress" (Reputation, 2017)
Why It’s Era-Defining: As confrontational as Reputation was in spots, the album’s real jaw-dropping moment came with “Dress,” the most explicitly seductive song to appear on a Taylor Swift LP to date. With a whispered and vulnerable ecstasy, Swift makes it clear to her Romeo that this time, her Yes can be assumed: “Only bought this dress so you could take it off.”
Most Taylor Lyric: “Say my name and everything just stops…” [music briefly but dramatically cuts out]
Ideal Live Guest: Bringing out FKA twigs for a medley of this one and twigs’ similarly electric “Two Weeks” could make for a secret moment in a crowded room that no one present would easily forget. — ANDREW UNTERBERGER
"Haunted" (Speak Now, 2010)
Why It’s Era-Defining: “Haunted” is one of Swift’s deep cuts that’s most fiercely loved by longtime fans. Mysterious and whimsical, it captures a darker strain of the magical themes the country-pop star perhaps unintentionally infused in the Speak Now era — and just as delightfully, it summarizes Bella Swan’s POV in New Moon of the Twilight saga with perfect accuracy. (Really.)
Most Taylor Lyric: “He will try to take away my pain/ And he just might make me smile/ But the whole time I’m wishing he was you instead”
Taylor’s Version Proposal: Hear us out: We want to hear this track mashed up with Laura Les’ hyperpop anthem of the same name (which surged in popularity after being featured in a 2022 episode of Euphoria). Taylor’s “Haunted” is already a banger bordering ever so slightly on the verge of pop punk, but infusing it with 100 Gecs’ apocalypticism would give it even more of a bite – something that would be as unexpected as it would be cool. — HANNAH DAILEY
"Safe & Sound" (feat. The Civil Wars) (2011)
Why It’s Era-Defining: Nearly a decade before Folklore, Taylor Swift embraced chilly folk (and character-inspired storytelling) for the first time via the spine-tingling Civil Wars collab “Safe & Sound.” The best of her several early-’10s soundtrack contributions, it showed that Swift’s musical reach was expanding as quickly as her songwriting maturity.
Most Taylor Lyric: The real Swift signature of this one is wordless, with her and the Civil Wars exchanging the eerie “ohh-ohhh‘s harmonies of the song’s spellbinding bridge.
Fun Fact: Though “Safe & Sound” wasn’t even nominated at the 2012 Oscars, it did win the 2013 Grammy for best song written for visual media — her only career win in that category, in four nominations to date. — A.U.
"I Wish You Would" (1989, 2014)
Why It’s Era-Defining: It’s pop, it’s fun, it’s dramatic, it’s romantic and yearning. With all that, “I Wish You Would” captures the overall feeling of 1989 perfectly.
Most Taylor Lyric: “We’re a crooked love/ In a straight line down/ Guess you wanna run and hide / But it made us turn right back around”
Ideal Live Guest: Haim! The retro synths and swelling chorus of “I Wish You Would” always reminded us of something that would fit into the sibling trio’s Days Are Gone era — and not only does Swift loves performing with them, but they’re opening her upcoming West Coast Eras Tour dates. So it’s all very possible. — R.A.
"You're on Your Own, Kid" (Midnights, 2022)
Why It’s Era-Defining: An eras tour in its own right, “You’re on Your Own, Kid” sees Taylor anxiously reflecting on phases of unrequited pining, mixed with career ambition and self-doubt verging on self-destruction — taking the occasional breather to caution herself: “You’re on your own, kid/ You always have been.” It’s a hard-earned happ(ier) ending though, as she ceases looking back in anger to conclude: “Everything you lose is a step you take… you’ve got no reason to be afraid.”
Most Taylor Lyric: “From sprinkler splashes to fireplace ashes/ I gave my blood, sweat, and tears for this/ I hosted parties and starved my body/ Like I’d be saved by a perfect kiss”
Taylor’s Version Proposal: Jack Antonoff’s pulsing synths provide an appropriately tense backdrop for Swift’s pacing recollections here, but we’d love to get a solo acoustic Taylor rendition here to give the song’s intricate storytelling a little more space to breathe. — A.U.
"Christmases When You Were Mine" (The Taylor Swift Holiday Collection, 2007)
Why It’s Era-Defining: While The Taylor Swift Holiday Collection was mostly an inessential set of covers and trifles, Taylor’s quality control level was already high enough at age 17 that she couldn’t let the seasonal EP go without offering at least one timeless gem: the acoustic tear-jerker “Christmases When You Were Mine,” perfectly capturing the sound of a heart too broken to be filled with Xmas spirit.
Most Taylor Lyric: “I’ll bet you got your mom another sweater/ Were your cousins late again?/ When you were putting up the lights this year/ Did you notice one less pair of hands?”
Screaming Color: The slow-burning red and black of a fireplace that just doesn’t quite provide the warmth you wish it would. — A.U.
"Daylight" (Lover, 2019)
Why It’s Era-Defining: The final track on Lover captures the album’s positivity and forward motion: the darkness of the Reputation era has given way to a gorgeous sunrise, which Swift and co-producer Jack Antonoff capture through warm synthesizer and echoing percussion. No song on Lover evokes the candy-colored clouds behind Swift’s head on the album cover quite like this one.
Most Taylor Lyric: “I once believed love would be burning red / But it’s golden”
Fun Fact: The spoken-word outro here, which starts with the line “I wanna be defined by the things that I love!” and is delivered through what sounds like a phone-call filter, has been interpreted by some fans as a more optimistic rejoinder of the answering-machine message that makes up the bridge of “Look What You Made Me Do” — “I’m sorry, the old Taylor can’t come to the phone right now…” — one album earlier. — JASON LIPSHUTZ
"I Know Places" (1989, 2014)
Why It’s Era-Defining: 1989 was the era of Harry Styles, as many fans believe that some tracks from the album were inspired by the One Direction superstar – “I Know Places” included. Its haunted synths and theme of urgency to hide feel appropriate in response to the media frenzy surrounding their short-lived relationship.
Most Taylor Lyric: “They are the hunters, we are the foxes/ And we run/ Just grab my hand and don’t ever drop it/ My love”
Ideal Live Guest: As much as we want to say Harry, he’d be better suited for an onstage “Style” moment. How about Selena Gomez instead? She and Swift have helped lift each other up through countless very public relationships and spotlighted drama, so it feels fitting for them to find that shelter Taylor sings of in each other. — R.A.
"Hey Stephen" (Fearless, 2008)
Why It’s Era-Defining: Though Taylor would become famous in her early career for thinly veiled missives about real-life exes who’d done her wrong, she could go the complete other way with it, too — like this grinningly giddy head-nodder about a real-life crush that’s having so much fun being in its feelings, it doesn’t majorly concern itself with whether they’re reciprocated or not.
Most Taylor Lyric: “All those other girls, well, they’re beautiful/ But would they write a song for you?”
Fun Fact: Yes, there is an actual Stephen: Stephen Barker Liles of country duo Love and Theft, who Taylor told about the song before its release. “I was very relieved when it turned out to be a nice song,” he recalled in 2009. — A.U.
"Question...?" (Midnights, 2022)
Why It’s Era-Defining: Some Midnights highlights serve as a great callback to Taylor’s Reputation era, where she isn’t afraid to hold back. She shakes off a bit of that sweetheart image yet again by sprinkling in more than a few expletive-filled tracks here, “Question….” being one of best.
Most Taylor Lyric: “One thing after another/ F–kin’ situations, circumstances/ Miscommunications, and I/ Have to say, by the way/ I just may like some explanations”
Ideal Live Guest: Let’s run back Taylor Swift x The 1975! It would be fun to hear Matty Healy take on that synthy bridge into the outro of the track. — B.K.
"Ronan" (Non-Album Single, 2012)
Why It’s Era-Defining: A gut-sledgehammering acoustic ballad about “a beautiful boy that died” — the titular three-year-old son of blogger Maya Thompson (credited as a co-writer, and sung by Swift from her perspective) — “Ronan” provided the devastating flipside to Swift’s more rose-colored early songs about childhood innocence. Though it hit the Hot 100’s top 20 and was eventually re-recorded for Red (Taylor’s Version), Swift has revisited “Ronan” very sparingly since its 2012 recording, careful not to dilute it with overexposure: The original was just too raw, too important.
Most Taylor Lyric: “What if I really thought some miracle would see us through?/ What if the miracle was even getting one moment with you?”
Screaming Color: Pitch black, as appropriately illustrated by the horror movie poster-looking single art. — A.U.
"Betty" (Folklore, 2020)
Why It’s Era-Defining: Taylor proves she really is capable of anything as a songwriter — including writing from the mind of a 17-year-old boy. The final addition to Folklore’s fictional love triangle (between Betty, James and a third unnamed protagonist) is certainly the lightest of the bunch, fusing teenage musings with good ol’ country music storytelling.
Most Taylor Lyric: “If you kiss me, will it be just like I dreamed it?/ Will it patch your broken wings?”
Taylor on Taylor: Taylor confirmed the outcome of the album’s love triangle in Folklore: The Long Pond Sessions: “In my head, I think Betty and James ended up together … but he really put her through it.” — DANIELLE PASCUAL
"Tis the Damn Season" (Evermore, 2020)
Why It’s Era-Defining: Sexy, sentimental, bittersweet and brutal, songs like this one (which is a narrative companion to “Dorothea”) demonstrated that Evermore wasn’t just Folklore Side B: Swift was in the midst of a musical rebirth and imperial songwriting phase that demanded an immediate follow-up LP.
Most Taylor Lyric: “I parkеd my car right between the Methodist/ And thе school that used to be ours/ The holidays linger like bad perfume.”
Taylor on Taylor: “[It’s about] Dorothea, the girl who left her small town to chase down Hollywood dreams – and what happens when she comes back for the holidays and rediscovers an old flame.” — JOE LYNCH
"Last Kiss" (Speak Now, 2010)
Why It’s Era-Defining: There are so many lyrical themes in this song that have become consistent Taylor motifs over the years, from the late-night timing (“Lit through the darkness at 1:58”) to the relationship mementos (“I’ll go sit on the floor wearing your clothes”) to beyond-specific details that allow listeners to play detective (“I ran off the plane that July ninth”). But what might be most affecting is how the dragging pace of the chorus seems to mimic the helpless feeling of a breakup, like you’re just trying to keep your head above water for one more breath. It really feels like you can draw a straight line from “Last Kiss” to Swift’s ultimate heartbreak masterpiece “All Too Well” two years later.
Most Taylor Lyric: “All that I know is I don’t know/ How to be something you miss”
Fun Fact: This is more of a fun coincidence, but — as many fans have pointed out — the lyric “Your name, forever the name on my lips” turned out to be pretty prescient: This song was allegedly written about Swift’s breakup with Jonas Brothers frontman Joe Jonas, and her current boyfriend of seven years Joe Alwyn also happens to be named Joe. (But are there any coincidences in Taylor’s world?) — KATIE ATKINSON
"Picture to Burn" (Taylor Swift, 2006)
Why It’s Era-Defining: Taylor takes that pent-up teenage angst and runs with it. Just the beginning of years of highly singable pop bangers, this upbeat track off her debut album showed that not all breakup songs have to be “Teardrops on My Guitar” — they can be fun and petty, too.
Most Taylor Lyric: “So watch me strike a match on all my wasted time”
Fun Fact: The version of this song first released in 2006 is not available on streaming. Why? Taylor removed a controversial lyric that threatened to spread false rumors about her ex’s sexuality. Will she bring it back for Taylor’s Version? Some Swifties are on board, but only time will tell. — D.P.
"Treacherous" (Red, 2012)
Why It’s Era-Defining: “Treacherous” is one of the best kinds of Taylor Swift songs: quiet and overlooked by the general masses, but filled line-to-line with some of her most gorgeous poetry. As Swift started officially knocking down pop music’s doors with the dancier, more radio-oriented tracks on Red, this song was a glowing reassurance to fans that she could still always be counted on to write the acoustic, lyric-focused ballads we fell in love with her for, too.
Most Taylor Lyric: “And all we are is skin and bone, trained to get along / Forever going with the flow, but you’re friction”
Screaming color: If songs like “State of Grace,” “I Knew You Were Trouble” and, of course, “Red” are burning red, then “Treacherous” is a softer, rosier shade: an understated, dusty pink. — H.D.
"Nothing New" (feat. Phoebe Bridgers) (Red (Taylor's Version), 2021)
Why It’s Era-Defining: Staring down her mid-20s, not even Taylor Swift was immune from a bit of a quarter-life crisis, as evidenced by this Red-era ballad facing sadly relatable questions of growing older but never wiser: “How can a person know everything at 18/ But nothing at 22?” Finally recorded for the Taylor’s Version series nearly a decade later, Swift brought along acolyte Phoebe Bridgers — an up-and-comer who maybe once made Taylor feel her years, but who’s perhaps since started looking over her shoulder herself — as if to tell her that, scary as these feelings may be, they too are nothing new.
Most Taylor Lyric: “She’ll know the way, and then she’ll say she got the map from me/ I’ll say I’m happy for her, then I’ll cry myself to sleep”
Fun Fact: According to a 2012 journal entry (included with special-edition CD packages of 2019’s Lover), Swift wrote “Nothing New” on an Appalachian dulcimer, a purchase inspired by Joni Mitchell’s classic Blue album. “I’ve been thinking a lot about getting older and irrelevancy and how all my heroes ended up alone,” she wrote — themes that would also inform’s Red similarly Joni-prompted “The Lucky One.” — A.U.
"My Tears Ricochet" (Folklore, 2020)
Why It’s Era-Defining: Is it a funeral dirge, written from the perspective of a murder victim haunting her own funeral? Maybe — but given the reference to her “stolen lullabies,” is the murder at hand the scorching end to her business relationship with Scott Borchetta? Whatever all the layers of this intricate song mean, the way it builds from somber to anthemic back to eerily quiet in the powerful production tells a story all its own.
Most Taylor Lyric: “And if I’m dead to you, why are you at the wake?”
Taylor on Taylor: “I wrote ‘My Tears Ricochet’ and I was using a lot of imagery that I had conjured up while comparing a relationship ending to when people end an actual marriage,” Swift told Entertainment Weekly in 2020. “All of a sudden, this person that you trusted more than anyone in the world is the person that can hurt you the worst … I think I wrote some of the first lyrics to that song after watching Marriage Story and hearing about when marriages go wrong and end in such a catastrophic way.” — KATIE ATKINSON
"Karma" (Midnights, 2022)
Why It’s Era-Defining: Revenge and calling out her haters is an omnipresent theme in Taylor’s latter few albums. In the Midnights era, it’s all about taking the high road — a lesson she learned the hard way via various public feuds. On this track, Taylor taps into the concept of karma, particularly her own good karma, to help shape her new narrative.
Most Taylor Lyric: “Sweet like honey, karma is a cat/ Purring in my lap ’cause it loves me.”
Fun Fact: In an April 2016 interview, Taylor Swift was asked, “What do you think is the most important life lesson for someone to learn?” Her response? “That karma’s real.” — B.K.
"Cornelia Street" (Live From Paris, 2019)
Why It’s Era-Defining: Carefully constructed with some of Lover’s most vulnerable lyrics, the studio version of “Cornelia Street” is already among Taylor’s best love songs. But her stripped-down rendition at 2019’s City of Lover concert in Paris to an intimate audience of her biggest fans — who already know all the words, just a couple weeks after the album was released — makes it all the more emotional.
Most Taylor Lyric: “We were a fresh page on the desk/ Filling in the blanks as we go”
Fun Fact: The rental that inspired the song was revealed as 23 Cornelia St. in Manhattan’s Greenwich Village neighborhood. The 5,400 square foot townhouse, complete with an indoor swimming pool, reportedly went up for rent once again in Nov. 2022 for a cool $45,000 a month. — D.P.
"Never Grow Up" (Speak Now, 2010)
Why It’s Era-Defining: A sort of childhood trilogy closer, following her self-titled album’s “Mary’s Song” and Fearless‘ “The Best Day” — a sweet lullaby to a little sister-type advising her to “stay this little … it could stay this simple.” The song is given unexpected gravity by its final verse, in which Taylor changes the perspective to her own, now scared and alone in the big city, swearing, “Wish I’d never grown up.”
Most Taylor Lyric: “To you, everything’s funny/ You got nothing to regret/ I’d give all I have honey/ If you could stay like that.”
Taylor on Taylor: “I look out into a crowd every night and I see a lot of girls that are my age and going through exactly the same things as I’m going through. Every once in a while I look down and I see a little girl who is seven or eight, and I wish I could tell her all of this.” — A.U.
"All You Had to Do Was Stay" (1989, 2014)
Why It’s Era-Defining: Possibly the most single-ready of 1989‘s deep cuts, “All You Had to Do Was Stay” was a crushingly direct, immediately enthralling you had one job kiss-off to an ex who saw the light a little too late. He had his chance, he blew it — and even if Taylor doesn’t sound too thrilled about movin’ on, it’s still outta sight, outta mind for her.
Most Taylor Lyric: “People like you always want back the love they gave away/ And people like me wanna believe you when you say you’ve changed”
Screaming Color: A blinding white, something both crystal clear and impossible to view in proper perspective. — A.U.
"Ivy" (Folklore, 2020)
Why It’s Era-Defining: On an album full of rustic folk anthems, “Ivy” is the woodsiest — quite literally, as Swift sings to the man who isn’t her husband, “Oh, I can’t/ Stop you putting roots in my dreamland” — and one of the more affecting, ornately produced portrayals of infidelity in her catalog.
Most Taylor Lyric: “So yeah, it’s a war/ It’s the goddamn fight of my life/ And you started it”
Fun Fact: Across the Folklore and Evermore track lists, “Ivy” is the only song that both Jack Antonoff and Aaron Dessner co-wrote along with Swift. All hands on deck for this folk jamboree! — J. Lipshutz
"I Forgot That You Existed" (Lover, 2019)
Why It’s Era-Defining: After embracing vitriol on Reputation, Swift opens Lover with a quick, cute announcement: her bitterness has morphed into “indifference” and obsessive brooding has been supplanted by forgetfulness. In this new era, she’s feeling more blessed than pressed and ready to move on.
Most Taylor Lyric: “I forgot that you existed/ I thought that it would kill me but it didn’t.”
Screaming Color: A blue-leaning periwinkle. — J. Lynch
"Death by a Thousand Cuts" (Lover, 2019)
Why It’s Era-Defining: Even at her happiest and most lovestruck, the superstar proved that she’s still more than capable of writing the perfect kind of breakup song that breaks (err, cuts) your heart into a million (or a thousand) pieces. And placing it immediately after “Cornelia Street” on the Lover tracklist? Talk about a one-two punch to the gut.
Most Taylor Lyric: “I look through the windows of this love/ Even though we boarded them up.”
Fun Fact: Swift revealed in a 2019 interview with Elvis Duran that she was inspired to write the song after watching the Neflix rom-com Someone Great — while director Jennifer Kaytin Robinson later reached out to reveal that she had come up with the idea for that film while driving cross-country after a breakup, listening to 1989 closer “Clean.” “I just wrote a song based on something she made, which she made while listening to something I made — which is the most meta thing that’s ever happened to me,” Tay gushed after learning of the mind-blowing coincidence. — G.R.
"Ours" (Speak Now Deluxe Edition, 2011)
Why It’s Era-Defining: “Ours” is the people’s princess of Taylor Swift songs. It started out as merely a bonus track on the deluxe edition of Speak Now, but ended up being championed so hard by fans, it later got the single/music video treatment and peaked at No. 13 on the Hot 100.
Most Taylor Lyric: “And any snide remarks from my father about your tattoos will be ignored / ‘Cause my heart is yours”
Taylor on Taylor: “I put this song on a bonus album,” Swift said in a behind-the-scenes clip from the “Ours” video shoot. “Fans found it, played it over and over again, requested it, and now it’s my single. That’s what I love so much about my fans, is they always let the best song win.” — H.D.
"Seven" (Folklore, 2020)
Why It’s Era-Defining: Within an album conceived as an experiment, “Seven” let Swift tinker with her songwriting and vocal style — the lyrics swim in bittersweet nostalgia, the singing floats around before becoming earthbound, all within an elliptical composition — while trying to unpack a friend’s domestic issues through memories. It’s all achingly beautiful on the surface, and quietly heartbreaking beneath it.
Most Taylor Lyric: “Sweet tea in the summer/ Cross your heart, won’t tell no other”
Screaming Color: Sepia, like a photograph taken during a long-ago afternoon and faded over time. — J. Lipshutz
"Soon You'll Get Better" (feat. The Chicks) (Lover, 2019)
Why It’s Era-Defining: Like “Ronan,” a song of unique difficulty within Taylor’s catalog for its bracing of the unbraceable: in this case, her mother’s ongoing struggle with cancer, and the potentially fatal implications. It’s a big enough ask that she calls in country legends the Chicks for backing vocals and emotional support, as they help urge Mama Swift to “get better soon” — because, as her daughter heartbreakingly insists to her, “you have to.”
Most Taylor Lyric: “And I hate to make this all about me/ But who am I supposed to talk to?/ What am I supposed to do/ If there’s no you?”
Taylor on Taylor: “It was a family decision to even put [“Better”] on the album, and I think songs like that that are really hard for you to write emotionally, maybe they’re hard to write and hard to sing because they’re really true… It’s something I’m so proud of. I can’t sing it.” — A.U.
"It's Nice to Have a Friend" (Lover, 2019)
Why It’s Era-Defining: Running a clipped 2:30, the crystalline “It’s Nice to Have a Friend” is both one of Taylor’s shortest songs and one her most fascinatingly enigmatic: an elliptical childhood-to-adulthood relationship saga that feels quintessentially Swiftian, but with just enough missing info and just enough sonic mystery to make you wonder if what she isn’t telling you is actually more important to the story. Coming second-to-last in the Lover tracklist, it’s a hell of a late-game curveball.
Most Taylor Lyric: “Something gave you the nerve/ To touch my hand/ It’s nice to have a friend.”
Taylor’s Version Proposal: Not saying we need a full 10 minutes or anything, but if ever there was a Taylor song that could use a more extensive revisiting to satisfy fan curiosity… — A.U.
"Speak Now" (Speak Now, 2010)
Why It’s Era-Defining: Daydreaming is perhaps Taylor Swift’s most fond pastime, if her songwriting is any indication. In the title track for her third studio album, Swift fantasizes about stopping her crush’s wedding with a different woman, as one does. The track fused two themes we often see in her early work – playing out scenarios in her head from beginning to end, and trying to stop her muse from ending up with the “wrong” girl.
Most Taylor Lyric: “I am not the kind of girl/ Who should be rudely barging in on a white veil occasion / But you are not the kind of boy/ Who should be marrying the wrong girl”
Taylor’s Version Proposal: We’d love to hear a male collaborator or influence jump in for the last chorus, where the POV changes from Swift’s to the groom’s. Perhaps one of the new wave of ronky tonk fellas, like Bailey Zimmerman. — B.K.
"Breathe" (feat. Colbie Caillat) (Fearless, 2008)
Why It’s Era-Defining: On the deep bench of Fearless, “Breathe” was never released as a single, but the Colbie Caillat collab was nominated for a Grammy (best pop collaboration with vocals) and also bucked Swift’s typical romantic subject matter by addressing the painful loss of a friend instead.
Most Taylor Lyric: “Never wanted this, never wanna see you hurt/ Every little bump in the road I tried to swerve”
Taylor on Taylor: “It’s a song about having to say goodbye to somebody, but it never blames anybody,” Swift wrote in the album notes. “Sometimes that’s the most difficult part: When it’s nobody’s fault.” — K.A.
"Jump Then Fall" (Fearless Platinum Edition, 2009)
Why It’s Era-Defining: It feels like a diary entry highlighting the joys of being a teenager in love, a theme that encompasses much of Fearless.
Most Taylor Lyric: “I like the way you sound in the morning/ We’re on the phone and without a warning/ I realize your laugh is the best sound I have ever heard”
Screaming Color: A sweet, strawberry-toned pink. “Jump Then Fall” is the innocent, idyllic little sister of Midnights’ “Maroon.” — R.A.
"Long Story Short" (Evermore, 2020)
Why It’s Era-Defining: Within the folk exercises of the Evermore track list, “Long Story Short” stands out as a light, self-aware synth-pop workout, with Swift reflecting on the backlashes she’s faced over the course of her career and how finding the right partner helped her forget about them. She sounds at ease throughout, and the production around her is intricate yet effortlessly conceived.
Most Taylor Lyric: “Fatefully/ I tried to pick my battles, ’til the battle picked me”
Taylor’s Version Proposal: Let’s speed this baby up and lean into the pristinely drawn hooks! There have been some sped-up remixes that have floated around TikTok since the release of Evermore, but an official version with a quicker tempo would make the chorus hit even harder, and potentially become a crossover smash. — J. Lipshutz
"No Body No Crime" (feat. Haim) (Evermore, 2020)
Why It’s Era-Defining: Swift consummated her years-long friendship with the Sisters Haim on record in the oddest possible way: a noir-y murder ballad about a woman killed by her husband and the vigilante detective who tries to get to the bottom of it that’s a stylistic and lyrical outlier in her catalog.
Most Taylor Lyric: “I think he did it, but I just can’t prove it.”
Taylor on Taylor: The victim in “No Body, No Crime” shares her name, Este, with one of the Haim sisters – and Swift imbued the character with details straight from the real-life Este. As Taylor told EW, “I had finished the song and was nailing down some lyric details and texted [Este], ‘You’re not going to understand this text for a few days but… which chain restaurant do you like best?’ and I named a few. She chose Olive Garden, and a few days later I sent her the song and asked if they would sing on it.” — ERIC RENNER BROWN
"Call It What You Want" (Reputation, 2017)
Why It’s Era-Defining: Reputation was an album whose truest pleasures mostly belied its larger messaging, including this sweet and simple number about finding love in the eye of the public s–tstorm. The title is a message of defiant acquiescence, Taylor acknowledging that she can’t always control a situation’s narrative, but finally liking her situation enough to be OK with that.
Most Taylor Lyric: “I want to wear his initial on a chain round my neck/ Not because he owns me/ But ’cause he really knows me”
Ideal Live Guest: Still impossible to hear that chain-initial lyric without thinking Ursher, baby. — A.U.
"Fifteen" (Fearless, 2008)
Why It’s Era-Defining: The way Taylor cut to the very core of being a teenage girl in this song while still being a teenage girl is nothing short of extraordinary. And beyond the romantic disappointments of high school, she pinpointed the dilemma of not knowing what “you’re supposed to be” when you’re younger – and making it clear that there’s plenty of time to figure it all out. Whether you’re listening to this as a teen or when you’re a bit older, its universal truths hit hard.
Most Taylor Lyric: “And when you’re fifteen/ Don’t forget to look before you fall”
Ideal Live Guest: After teaming up on the acoustic ballad for a duet at the 2009 Grammys, it would be incredible for the then-16-year-old Miley Cyrus and the then-19-year-old Taylor to revisit the song nearly, well, 15 years later. — K.A.
"End Game" (feat. Future & Ed Sheeran) (Reputation, 2017)
Why It’s Era-Defining: When Taylor dropped her sixth studio album, “End Game” was the first song on the tracklist that sounded like an immediate hit. Enlisting Ed Sheeran and Future for a genre-melding party of pop, hip-hop and wistful R&B, the single remains the Reputation era track besides “Look What You Made Me Do” that most feasibly could’ve also been a Hot 100 No. 1.
Most Taylor Lyric: “I swear I don’t love the drama, it loves me” — but also have to give an honorable mention to the genius that is “I bury hatchets, but I keep maps of where I put ‘em.”
Ideal Live Guest: In a perfect world, it would be quite the moment to see both Future and Sheeran join Swift on stage to perform “End Game,” but in a clinch, we’ll take one or the other. — G.R.
"Gold Rush" (Evermore, 2020)
Why It’s Era-Defining: Taylor works with Jack Antonoff here to depict jealousy in the dreamiest way possible. Perfectly pinpointing those frustrating feelings of falling for someone who’s conventionally swoon-worthy, the Evermore track is simultaneously a serotonin boost and reality check for hopeless romantics everywhere.
Most Taylor Lyric: “I don’t like slow motion, double vision in rose blush”
Ideal Live Guest: Hear us out: Selena Gomez. She’s never gone this folky in her music, but as both she and Taylor once dated two of America’s biggest heartthrobs, it would be pretty iconic. — D.P.
"The Man" (Lover, 2019)
Why It’s Era-Defining: “The Man” was a pointed response to the sexism Taylor Swift had faced up until that point. Arriving after the 2017 boom of the #MeToo era and on her most political album to date, the song cemented itself as a female empowerment anthem, as Swift cemented herself as an ally to women, the LGBTQIA community and more while taking a direct shot at her male counterparts, even calling out one by name.
Most Taylor Lyric: “Let the players play/ I’d be just like Leo/ In Saint-Tropez”
Fun Fact: Like any TS project, Easter Eggs are abundant in the music video, which served as her solo directorial debut, but the biggest surprise and delight of them all was Swift’s prosthetic transformation to star as The Man in the video. — B.K.
"Sparks Fly" (Fearless, 2008)
Why It’s Era-Defining: It’s got cheesy romance scenes involving rain. It’s got a reference to a guy’s eye color (green). It’s got plenty of big drum hits, perfect for hair flip moments. Basically, it’s got all the hallmarks of a great early Taylor song, marking something of a final victory lap using the songwriting tools she mastered in her first three albums, before going on to release more experimental singles on Red.
Most Taylor Lyric: “Drop everything now, meet me in the pouring rain/ Kiss me on the sidewalk, take away the pain”
Screaming color: Maybe this is a tad obvious, but just like Fourth of July sparklers, this track is 100% gold. — H.D.
"The Archer" (Lover, 2019)
Why It’s Era-Defining: A fan favorite whose synth-pop splits the difference between the bright maximalism of 1989 and the lush tension of Midnights — connected with one of Taylor’s most vivid lyrics of the period — “The Archer” was one of Lover‘s truest bullseyes.
Most Taylor Lyric: “All the king’s horses, all the king’s men/ Couldn’t put me together again/ ‘Cause all of my enemies started out friends”
Taylor’s Version Proposal: With those gorgeous keys and nervously pulsing drums, there’s some serious 12″ remix potential here — maybe from Stuart Price if he isn’t too busy? — A.U.
"I Did Something Bad" (Reputation, 2017)
Why It’s Era-Defining: Taylor kicked off her Reputation era with the divisive hiss of “Look What You Made Me Do,” but she just as easily made much the same statement with “I Did Something Bad” if she’d felt like it. Though not released as a single, the good-girl-gone-bad anthem was a euphoric high point on the Reputation Stadium Tour, with Swifties in every stadium feeling the (literal) fire of their queen’s wrath as she burned her carefully curated image to the ground with a smile on her face.
Most Taylor Lyric: “They’re burning all the witches, even if you aren’t one.”
In Screaming Color: How would you describe the color of fire? Whatever the blaze is after scorching its way well past burning red and golden daylight, that’s what “I Did Something Bad” looks like. — G.R.
"This Is Me Trying" (Folklore, 2020)
Why It’s Era-Defining: As a person who once seemed to approach situations like report cards waiting to be filled with straight As, Swift acknowledges that you can get “so ahead of the curve, the curve became a sphere / Fell behind on my classmates.” Exemplifying the enormous personal and artistic growth that Folklore speaks to, “This Is Me Trying” makes the case that the runner steadfastly huffing and wheezing to cross the finish line dead-last is as valid as the winner.
Most Taylor Lyric: “Pouring out my heart to a stranger / But I didn’t pour the whiskey”
Fun Fact: When Simone Biles returned to the Tokyo Summer Olympics after a brief mental health break, Swift recorded a video salute to the gold-medal champion set to this song, saying: “When you have the attention of the world, everything you do takes on a bigger meaning. It can be a heavy burden. It can be a chance to change everything.” — J. Lynch
"New Romantics" (1989 Deluxe Edition, 2014)
Why It’s Era-Defining: The little bonus track that could stood out so much that it was released as the seventh and final single of the 1989 Era, alongside a tour-recap video thanking her millions of concertgoers. To this day, it’s still shocking that this song wasn’t included on the standard album, since it so comfortably fits with the project’s ’80s-inspired, synth-forward theme — but the heartbreak national anthem found its audience anyway.
Most Taylor Lyric: “Baby, I could build a castle/ Out of all the bricks they threw at me”
Taylor’s Version Proposal: Perhaps to finally give it the shine it deserves, Taylor could release the re-recorded “Romantics” as the lead single from 1989 (Taylor’s Version), along with a proper music video. #JusticeForNewRomantics — K.A.
"Mary's Song (Oh My, My My)" (Taylor Swift, 2006)
Why It’s Era-Defining: Taylor Swift’s first album didn’t have the deepest bench past the singles, but “Mary’s Song” was her first truly essential deep cut: a lilting lifelong love story told economically in three verses and change, inspired by Taylor’s real-life neighbors and every bit as heartwarming as you’d expect.
Most Taylor Lyric: “I’ll be eighty-seven; you’ll be eighty-nine/ I’ll still look at you like the stars that shine”
Taylor on Taylor: “I wrote this song about a couple who lived next door to us. They’d been married forever and they came over one night for dinner, and were just so cute … it was really comforting to know that all I had to do was go home and look next door to see a perfect example of forever.” — A.U.
"Better Man" (Red (Taylor's Version), 2021)
Why It’s Era-Defining: Though by 2016, Swift’s own recordings had long since moved on from country and focused on chart domination in the pop music sphere, she proved she could still have a solid grip on the country music charts, through writing this piercing heartbreak ballad that country group Little Big Town released in October of that year. “Better Man” became a two-week No. 1 on Billboard‘s Country Airplay chart. In 2021, Swift released her own sighing version of the song as part of her re-recorded album Red (Taylor’s Version).
Most Taylor Lyric: “You push my love away like it’s some kind of loaded gun”
Ideal Live Guest: The obvious pick here would be welcoming Little Big Town to offer the group’s illustrious harmonies, but another contender could be Swift’s longtime friend and fellow country artist Kelsea Ballerini, whose softly conversational vocals would also fit well with this track. — J.N.
"The 1" (Folklore, 2020)
Why It’s Era-Defining: As the ice-breaking opening track on Folklore, “The 1” sets the stage for an album that strips away a lot of Swift’s production bells and whistles but doesn’t sacrifice the witty wordplay or hopeless romanticism she does best. It’s one of the woodsy album’s most upbeat songs, though it’s full of lyrical longing.
Most Taylor Lyric: “In my defense, I have none/ For never leaving well enough alone”
Screaming Color: Hyacinth. The purple flower apparently represents “sorrow, regret and forgiveness” — a perfect trio for this reflective song. — K.A.
"The Other Side of the Door" (Fearless Platinum Edition, 2009)
Why It’s Era-Defining: In spite of being a deluxe bonus track from Fearless, “The Other Side of the Door” is an absolute banger nearly rivaling the likes of “You Belong With Me” and “Love Story.” Swift has you dancing so hard straight from the very first chorus, you’re practically levitating by the time she gets to her peak teen-Taylor outro.
Most Taylor Lyric: Honestly, the whole outro. “With your face and the beautiful eyes/ And the conversation with the little white lies/ And the faded picture of a beautiful night/ You carried me from your car up the stairs…”
Screaming color: It’s giving burnt orange. Intense and pleading, the color of the sun setting on a pastoral country house where doors slam and young lovers make up within hours. — H.D.
"Teardrops on My Guitar" (Taylor Swift, 2006)
Why It’s Era-Defining: Taylor’s first real crossover hit, “Teardrops” was one of the most effective country singles of the late ’00s — with a weeping melody, a relatably pining lyric, some immaculate chorus harmonies, and a title phrase that cleverly ensured that you knew the teen phenom behind it was playing and writing as well as singing.
Most Taylor Lyric: “I drive home alone, as I turn out the light/ I’ll put his picture down and maybe get some sleep tonight”
Ideal Live Guest: Kacey Musgraves sure would sound great on those harmonies — and/or on tear-stained acoustic support. — A.U.
"Right Where You Left Me" (Evermore Deluxe Edition, 2020)
Why It’s Era-Defining: The Evermore bonus track is another instance of New Taylor really showing off her range, both musically and vocally. With Aaron Dessner on banjo, it’s almost reminiscent of her Speak Now era — but a bit more grown up (and slightly more depressing).
Most Taylor Lyric: “She’s still 23 inside her fantasy”
Screaming Color: A muted yellow. People can see that the spotlight is on you, but it’s not bright enough to catch the attention of those you care about most. — D.P.
"Willow" (Evermore, 2020)
Why It’s Era-Defining: “Willow” may have blasted to the top of the Hot 100 chart upon the December 2020 release of Evermore thanks to fan excitement over the unexpected Folklore follow-up — but its beguiling harmonies, soothing guitar picking, chamber-folk production and lyrics of romantic devotion turned it into the most enduring hit of that Taylor era, climbing to No. 1 on the Adult Pop Airplay chart four months after its release.
Most Taylor Lyric: “They count me out time and time again … But I come back stronger than a ‘90s trend”
Ideal Live Guest: Picture it: you’re at a Taylor Swift show, and your ear recognizes the finger-picked guitar line that opens “Willow”… but it’s being played by an electric guitar with a quicker tempo and a lot more crunch. The rip-roaring production kicks in, and somehow, Swift has re-imagined “Willow” as a pop-punk love song. And then, to take on the second verse and duet on the chorus, out walks WILLOW. — J. Lipshutz
"The Story of Us" (Speak Now, 2010)
Why It’s Era-Defining: As she grew into young adulthood, Taylor’s understanding of all the facets of love and heartache evolved — which she demonstrates on “The Story of Us,” one of the closest things we have in her catalog this side of “Paper Rings” to a pop-punk anthem. Sometimes breakups aren’t just sad: they’re awkward and confusing and all kinds of messy. As the set’s only radio single to peak outside the top 40 on the Hot 100, the song remains the most underrated single of the Speak Now era. The end.
Most Taylor Lyric: “Oh, I’m scared to see the ending/ Why are we pretending this is nothing/ I’d tell you I miss you but I don’t know how/ I’ve never heard silence quite this loud.”
Taylor’s Version Proposal: Considering Taylor confirmed back in a 2010 USA Today interview that the subject at the song’s core is the same musician she ripped to shreds on “Dear John,” perhaps it would be a safer gamble for a particular tattooed rocker to offer his signature guitar to this one than duet on the latter. — G.R.
"We Are Never Ever Getting Back Together" (Red, 2012)
Why It’s Era-Defining: As Swift’s first collaboration with Swedish pop savants Max Martin and Shellback, and the first of her four Hot 100 No. 1s with the duo, “We Are Never Ever Getting Back Together” marked the beginning of a new era for the musician. But it also was a euphoric exclamation at the end of another era — marking the pinnacle of Swift’s pop-country mastery before she pivoted further into the pop world.
Most Taylor Lyric: “You would hide away and find your peace of mind/ With some indie record that’s much cooler than mine”
Ideal Live Guest: Jenny Lewis. Lean into the decade-old drama, Taylor! (Plus, wouldn’t the indie-rocker sound great on this one?) – E.R.B.
"New Year's Day" (Reputation, 2017)
Why It’s Era-Defining: Long after Swift had transitioned from country to pop with her album 1989 in 2014, this introspective piano ballad (and perfect Reputation closer) was released to country radio in late 2017 — marking a homecoming of sorts, as Swift’s first entry on Billboard’s Country Airplay chart since 2014’s “Shake It Off” reached No. 58.
Most Taylor Lyric: “Please don’t ever become a stranger whose laugh I could recognize anywhere.”
Screaming Color: The stark blue of a late morning after a raucous party. — J.N.
"Long Live" (Speak Now, 2010)
Why It’s Era-Defining: The longest-by-runtime album of Taylor Swift’s career demanded an epic capper, and it got one in the sweeping, senior yearbook-worthy “Long Live” — a dragon-slaying, name-saying, confetti-soaked anthem of triumph with one goal in mind above all else: “We will be remembered.” Got that.
Most Taylor Lyric: “And the cynics were outraged/ Screaming, “This is absurd”/ ‘Cause for a moment, a band of thieves in ripped-up jeans/ Got to rule the world”
Taylor’s Version Proposal: Could we coax Mutt Lange back to the decks to give this the full ’80s power ballad treatment it’s so desperately calling out for? — A.U.
"Illicit Affairs" (Folklore, 2020)
Why It’s Era-Defining: “Illicit Affairs” is among the most criminally underrated tracks of Swift’s career. If “My Tears Ricochet” didn’t exist, it could have easily been given the honor of Track 5 placement — always the most devastating song on any TS album — on Folklore.
Most Taylor Lyric: “Don’t call me kid/ Don’t call me baby/ Look at this idiotic fool that you made me/ You taught me a secret language I can’t speak with anyone else”
Ideal Live Guest: Can’t you just already hear Phoebe Bridgers singing this song? The treachery, the melancholia, the whispered melody that pierces straight to the heart – everything about “Illicit Affairs” is calling the indie-rock star’s name. And frankly, “Nothing New” simply wasn’t enough Swift/Bridgers content; we need more. — H.D.
"22" (Red, 2012)
Why It’s Era-Defining: After each warm, playful acoustic verse, “22” explodes into a synth-y sunburst on the Max Martin & Shellback-produced chorus. A perfect counterpoint to the maximalist intensity of previous Red single “I Knew You Were Trouble,” this cheery sing-along demonstrated that Swift was ready to have fun in the pop arena, too.
Most Taylor Lyric: “We’re happy, free, confused and lonely in the best way”
Fun Fact: When Taylor Swift began a lucrative, long-term partnership with Diet Coke in 2013, “22” soundtracked the first TV commercial she starred in for the soda, which premiered during American Idol. — J. Lynch
"Mastermind" (Midnights, 2022)
Why It’s Era-Defining: Relatively low-key for a Taylor Swift LP’s final track, but no less arresting for it: atop OMD-worthy synth arpeggios and a racing heartbeat, Taylor plays with her career-long reputation for calculatedness to winkingly inform her lover that he was a helpless victim of her fiendish plot all along: “What if I told you I’m a mastermind?/ And now you’re mine/ It was all by design.” A little clever-clever for sure, but also just pretty damn clever.
Most Taylor Lyric: “And I swear/ I’m only cryptic and Machiavellian ’cause I care”
Ideal Live Guest: Truly, the only male pop mastermind worthy of playing Taylor’s other half in this one would have to be her old fail-to-plan, plan-to-fail collaborator Max Martin. Can’t vouch for his singing voice, though, so might also need to give him some bleeps to bloop on-stage just in case. — A.U.
"Our Song" (Taylor Swift, 2006)
Why It’s Era-Defining: Oh, the sugary sweet lyrics of teenage love! Taylor Swift’s debut album was saturated with references to that “butterflies in your stomach” feeling. With mentions of slamming screen doors, her mama and praying to God, it was the perfect country-pop tune to help introduce Swift to the larger world, and that it did – it became her first Hot Country Songs No. 1, and reached the Hot 100’s top 20.
Most Taylor Lyric: “I was ridin’ shotgun with my hair undone/ In the front seat of his car…”
Fun Fact: Swift wrote “Our Song” for her ninth grade talent show, and pushed to include it on the album after seeing how popular it was with her classmates. — B.K.
"The Way I Loved You" (Fearless, 2008)
Why It’s Era-Defining: Full of angst, yearning and a sprinkle of naiveté, this song finds a teenaged Swift at her most delightfully dramatic – which, in many ways, is the whole point of Fearless.
Most Taylor Lyric: “I miss screaming and fighting and kissing in the rain/ And it’s 2:00 a.m. and I’m cursing your name”
Fun fact: “The Way I Loved You” is one of at least seven Taylor Swift songs to include mention of either “2 a.m.” or a time within 30 minutes of 2 a.m. — H.D.
"Red" (Red, 2012)
Why It’s Era-Defining: Opening with a wistful, yearning banjo, “Red” deftly and almost imperceptibly switches into higher gears until you feel like you’re launching that Maserati onto an open highway with that pummeling pop-rock chorus – and wait, how is this thing already over the speed limit?! As the title track to her soft launch into the pop realm, “Red” had a lot of heavy lifting to do, but Swift seems like she’s doing bench presses with her fingertips on this exhilarating zero-to-90-and-right-back-to-zero ride.
Most Taylor Lyric: “Fighting with him was like trying to solve a crossword/ And realizing there’s no right answer.”
Screaming Color: Puce. Yeah, puce. That makes sense. — J. Lynch
"Shake It Off" (1989, 2014)
Why It’s Era-Defining: With its thumping drums, brassy stabs, and infectious – for some, maybe too infectious – vocal hook, 1989‘s lead single heralded the true arrival of Taylor the Pop Star. The song’s bridge hasn’t necessarily withstood the test of time, but Swift’s vocal runs coming out of it have.
Most Taylor Lyric: “While you’ve been gettin’ down and out about the liars and the dirty, dirty cheats of the world / You could’ve been gettin’ down to this sick beat”
Fun Fact: Which of her songs did Swift choose to perform with Paul McCartney and Jimmy Fallon at the afterparty for Saturday Night Live‘s 40th anniversary special in February 2015? None other than “Shake It Off.” — E.R.B.
"Midnight Rain" (Midnights, 2022)
Why It’s Era-Defining: The more time we get to spend with Midnights, the more haunting “Midnight Rain” becomes: from the call-and-response effect between Swift’s voice and her own pitched-down hook, to the bleary production that makes room for lonely handclaps, to the pensive outro that never circles back around the chorus, the song crystallizes the late-night vibe of its host album.
Most Taylor Lyric: “And I never think of him/ Except on midnights like this”
Taylor’s Version Proposal: Give us an effects swap — let’s hear the pitched-down parts sung in Swift’s natural voice and the verses turned inside out. The product would sound jarring, but probably pretty effective! — J. Lipshutz
"Lover" (Lover, 2019)
Why It’s Era-Defining: This hazy waltz feels like Taylor Swift’s more mature but equally satisfying return to some of the whimsical, romantic tracks that populated earlier albums like Fearless.
Most Taylor Lyric: “With every guitar string scar in my hand, I take this magnetic force of a man to be my lover”
Surprise Guest: Given that guitar ace Keith Urban covered this song in concert shortly after it released, another full-on collaboration between these two would be magic. Swift previously welcomed Urban during her 1989 World Tour stop in Toronto in 2015. — J.N.
"White Horse" (Fearless, 2008)
Why It’s Era-Defining: Is there a more heartbreaking song in Swift’s early oeuvre than “White Horse”? The country-pop ballad plays as the polar opposite of Fearless lead single “Love Story”: Rather than saying yes to a small-town Romeo’s romantic proposal, the song ends with Taylor putting the two-timer and her old life in the rearview, bound for greener pastures in a bittersweet happy ending all her own.
Most Taylor Lyric: “‘This is a big world, that was a small town/ There in my rearview mirror disappearing now/ And it’s too late for you and your white horse to catch me now.”
Fun Fact: The original music video starred Laguna Beach heartthrob Stephen Colletti as Taylor’s love interest. Coincidentally, many a millennial Swiftie is sure to think of the One Tree Hill alum anytime they listen to “Hey Stephen,” the lovestruck ditty that comes right before “White Horse” on the album’s tracklist. — G.R.
"...Ready For It?" (Reputation, 2017)
Why It’s Era-Defining: The pop world might not have been ready to embrace the bass-bombing drops of Taylor Swift’s Reputation kickoff — and the gaudy sci-fi of the video did it no favors. But the ear-splitting bombast of “…Ready for It?” cloaked one of her craftiest pop songs of the decade, a punch-drunk love song in MCU trappings, Swift playing the baddie but also openly admitting “I’m so very tame name now.”
Most Taylor Lyric: “He can be my jailer, Burton to this Taylor/ Every lover known in comparison is a failure.”
Taylor on Taylor: “‘..Ready For It’ is basically [presented as] finding your partner in crime, and it’s like, ‘Oh my god we’re the same, we’re the same, oh my god! Let’s rob banks together, this is great!'” — A.U.
"Back to December" (Speak Now, 2010)
Why It’s Era-Defining: As soon as that chiming guitar kicks in and is washed over by orchestral strings, we’re transported back to a time when Swift’s focus was on towering country-pop power ballads like this one. “Back to December” is a gut-punch of a mea culpa to a jilted ex, and it grows more refined with age.
Most Taylor Lyric: “You gave me roses, and I left them there to die”
Fun Fact: After years of hints and rumors, Taylor Lautner confirmed in 2016 that the line “I miss your tan skin, your sweet smile,” and the entirety of “Back To December” was indeed about his short-lived romance with Swift. — J. Lipshutz
"Begin Again" (Red, 2012)
Why It’s Era-Defining: Red mostly represented Taylor’s pivot away from the world of country towards the wider realm of top 40 pop — but she still couldn’t resist closing the set with this pitch-perfect twangy ballad about a faith-restoring new relationship, as if to remind Nashville what they’d be missing in the years to come.
Most Taylor Lyric: “You said you never met one girl who/ Had as many James Taylor records as you/ But I do”
Ideal Live Guest: Sweet Baby James would be the obvious answer, but we feel like Paramore frontwoman Hayley Williams — who has her own Music City roots, and her own heartbursting early-2010s love song along similar lines — could provide some absolutely knee-buckling harmonies on this one. — A.U.
"Wildest Dreams" (1989, 2014)
Why It’s Era-Defining: “Wildest Dreams” is, from a songwriting perspective, one of Swift’s best pieces of work ever. It’s catchy, poetic, cinematic, and beautifully structured – even those who may have gotten sick of its near-constant radio play in 2015 could surely admit that it was a damn good song. Combined with fellow 1989 singles like “Blank Space” and “Style,” it proved that she had finished what she started with Red, officially becoming a queen of pop hooks.
Most Taylor Lyric: “You’ll see me in hindsight/ Tangled up with you all night/ Burning it down”
Taylor’s Version Proposal: Gather up all of the young female artists who’ve cited Tay as an inspiration – Olivia Rodrigo, Sabrina Carpenter, Maisie Peters, Rachel Zegler, the list goes on – and make their “wildest dreams” come true by getting all of them to sing harmonies on a lush, layered bonus version of the song on 1989 (Taylor’s Version). — H.D.
"Fearless" (Fearless, 2008)
Why It’s Era-Defining: As obvious as it sounds, “Fearless” is the song everyone thinks of when picturing the Fearless era. It’s the ultimate romanticizing of life, and a song that is meant to be sung at the top of your lungs — two things that Swift is uniquely good at creating.
Most Taylor Lyric: “And I don’t know how it gets better than this/ You take my hand and drag me head first/ Fearless”
Fun Fact: Speaking of romanticizing life, the concept of “Fearless” came from Swift’s imagination. She told That’s Country in the past that her 2008 album’s title track isn’t about anyone in particular, and describes “the best first date I haven’t had yet.” — R.A.
"Tim McGraw" (Taylor Swift, 2006)
Why It’s Era-Defining: This is the song that started it all. Her debut single. Her first Hot 100 chart entry. Her first top 10 country hit. And her first in a long line of wistful lost-love songs that paint a vivid picture through diary-entry lyrics and personal details (“Georgia stars,” “Chevy truck,” “that little black dress”). This set the blueprint for decades of autobiographical music to come.
Most Taylor Lyric: “He said the way my blue eyes shined put those Georgia stars to shame that night/ I said, ‘That’s a lie’”
Fun Fact: Taylor brought out Tim McGraw and his wife Faith Hill to perform the song with her during a 2018 Reputation Tour stop in Nashville. — K.A.
"Maroon" (Midnights, 2022)
Why It’s Era-Defining: Like the title track off Red, Taylor uses the color of love as the driving force of the narrative in “Maroon.” However, written nearly a decade later, the Midnights track digs deeper — recollecting memories and feelings much more complex than its younger sister.
Most Taylor Lyric: “And I wake with your memory over me/ That’s a real f–king legacy to leave”
Fun Fact: Taylor subtly includes nine different single-word references to deep shades of red in the lyrics. Have you caught them all? (Answers: rosé, wine, burgundy, blood, rust, scarlet, rose, ruby and of course, maroon.) — D.P.
"Getaway Car" (Reputation, 2017)
Why It’s Era-Defining: As with “Love Story,” Swift references another famous couple here. “Getaway Car” wields a cinematic quality as it compares a whirlwind, rebound romance to Bonnie and Clyde-esque heist, with similar sweep and pulse-racing excitement.
Most Taylor Lyric: “Don’t pretend it’s such a mystery/ Think about the place where you first met me ridin’ in a getaway car”
Ideal Live Guest: “Nonsense” singer Sabrina Carpenter would add an extra dose of verve and defiance. — J.N.
"Exile" (feat. Bon Iver) (Folklore, 2020)
Why It’s Era-Defining: The Folklore era wasn’t exactly primed for showstoppers, but this most theatrical ballad of Taylor Swift’s 2020s sees her trading yearning bars of desperation with Justin Vernon of Bon Iver like they’re co-starring in a home production of Once. That’s a good thing, btw: In a catalog hardly lacking for high drama, few Swift moments land as resoundingly as Vernon declaring “You never gave a warning sign!” over Journey-worthy piano, while she responds in counterpart, “I gave SO MANY signs.”
Most Taylor Lyric: “Second, third, and hundredth chances/ Balancin’ on breaking branches/ Those eyes add insult to injury”
Taylor’s Version Proposal: A switcheroo! We’re sure Taylor’s been dying to hear what her voice would sound like leading the way on that climactic refrain, howling “So step right out, there is no amount/ Of crying I can do for you” while her partner offers backing commentary. — A.U.
"Welcome to New York" (1989, 2014)
Why It’s Era-Defining: “Welcome to New York, it’s been waiting for you.” With a single sentence, Taylor gave small-city dreamers a mantra and a rallying cry as she opened 1989. Determined to show her critics she could write about more than her love life, the superstar penned a neon-lit love letter to the city that never sleeps, where everyone goes to reinvent themselves — complete with her first outright advocacy for the LGBTQ community with the line, “Everbody here was someone else before/ And you can want who you want/ Boys and boys and girls and girls.”
Most Taylor Lyric: “Everybody here wanted something more/ Searching for a sound we hadn’t heard before/ And it said, ‘Welcome to New York, it’s been waiting for you.’”
Taylor on Taylor: “I dreamt about moving to New York, I obsessed about moving to New York and then I did it. The inspiration that I found in that city is kind of hard to describe and hard to compare to any other force of inspiration I’ve ever experienced in my life,” Swift told Good Morning America ahead of revealing the track back in 2014. — G.R.
"Holy Ground" (Red, 2012)
Why It’s Era-Defining: Much like the rest of Red, the rock-tinged, Jeff Bhasker-produced “Holy Ground” represented a new step in Swift’s career in which she was openly experimenting with different genres.
Most Taylor Lyric: “Spinning like a girl in a brand new dress/ We had this big wide city all to ourselves/ We blocked the noise with the sound of ‘I need you’/ And for the first time I had something to lose.”
Fun Fact: The hidden message for this song in the Red liner notes was, “When you came to the show in SD” — which Swifties linked to Joe Jonas, who attended his ex-girlfriend’s Speak Now Tour stop in San Diego. — R.A.
"Lavender Haze" (Midnights, 2022)
Why It’s Era-Defining: After Folklore and Evermore‘s dual indie-folk excursions, “Lavender Haze” – as Midnights‘ quickly hooking opening track, the first sounds fans heard of Swift’s new era, following her decision not to release an advance single from the set – stylishly indicated the star’s return to a more mainstream pop aesthetic.
Most Taylor Lyric: “I’m damned if I do give a damn what people say”
Taylor’s Version Proposal: Maybe it’s just because a color in the purple family calls Future to mind or that “Lavender Haze” would be a top contender for a Swift-branded cannabis line but… given its narcotic, pulsating beat, would any of her songs be better chopped and screwed? — E.R.B.
"Gorgeous" (Reputation, 2017)
Why It’s Era-Defining: A younger, more sheltered Swift might’ve met the lyrics of “Gorgeous” with stern disapproval, but Reputation-era Swift wasn’t above the illicit thrill of flirting with someone who isn’t your partner. Heck, she’s not even ashamed of it, musing about cheating in a sing-song cadence while dropping lines about stumbling “home to my cats” and inserting cheeky triangle dings. Previously, Swift was wont to detail the pain of being cheated on; here, she explores the effervescent rush of being bad.
Most Taylor Lyric: “You make me so happy, it turns back to sad / There’s nothing I hate more than what I can’t have”
Fun Fact: The baby voice at the top of the song belongs to the daughter of Blake Lively and Ryan Reynolds, James Reynolds. — J. Lynch
"Mean" (Speak Now, 2010)
Why It’s Era-Defining: Whether it’s read as a universal rejection of schoolyard bullies or a specific score to settle with a music critic who doubted Swift’s singing voice, “Mean” deftly balances personal embarrassment, tongue-in-cheek humor and full-throated statements of overcoming the haters and naysayers. At the peak of her country-pop powers, Swift’s mix of bluegrass-adjacent production — banjo, fiddle, handclaps and mandolin — and big, juicy sing-along moments is otherworldly here.
Most Taylor Lyric: “Someday, I’ll be living in a big old city / And all you’re ever gonna be is mean”
Fun Fact: At the 2012 Grammys, where “Mean” won best country solo performance and best country song, Swift got one last shot in at its targeted doubters — performing the song on the telecast, she changed the final chorus to, “Someday, I’ll be singing this at the Grammys.” — J. Lipshutz
"Out of the Woods" (1989, 2014)
Why It’s Era-Defining: From its jarring intro to its stark close, “Out of the Woods” obliterates the idea that there’s any sort of formula for creating a great pop song. The 1989 single looks back at a past relationship with both anxiety and exhilaration, and its production fits those same emotions to a T.
Most Taylor Lyric: “The rest of the world was black and white/ But we were in screaming color”
Taylor on Taylor: Some critics argued that the chorus is too repetitive — but little did they know, that was the whole point. “This song sounds exactly like that frantic feeling of anxiety and questioning. But it stresses that even if a relationship is breakable and fragile and full of anxiety, it doesn’t mean that it isn’t worthwhile.” — D.P.
"Enchanted" (Speak Now, 2010)
Why It’s Era-Defining: The emotional climax to Speak Now — no small feat there — “Enchanted” also sorta served as the capper to Taylor Swift’s fairytale era, with the singer-songwriter then beginning her 20s and too aware of love’s realities to treat it so fantastically. Tellingly, it’s not some grand love story that leaves her wonderstruck this time out, but just a chance encounter at a party that has her up at 2:00 a.m. praying, “Please don’t be in love with someone else/ Please don’t have somebody waiting on you.”
Most Taylor Lyric: “Your eyes whispered, ‘Have we met?'”
Screaming Color: Lavender, in that early-signature way that Taylor’s music would never quite be again. — A.U.
"The Last Great American Dynasty" (Folklore, 2020)
Why It’s Era-Defining: Proof positive that Swift could spin a marvelous tale of historical fiction among the Folklore of her surprise 2020 album, “The Last Great American Dynasty” also gave fans a bit of insight into just how Swift might want to be remembered in the annals of history — as a fiercely independent, slightly mad and gleefully misunderstood woman cut from the same cloth as socialite Rebekah Harkness, the deed to Holiday House and all.
Most Taylor Lyric: “I had a marvelous time ruining everything.”
Fun Fact: While Swift sings of Harkness “winning on card game bets with Dalí” in the song’s second verse, the middle-class divorceé-turned-heiress actually had her remains interred in the Spanish Surrealist’s famed “Chalice of Life,” which she bought from him for a whopping $250,000. — G.R.
"Style" (1989, 2014)
Why It’s Era-Defining: From her sleek bob to her ripped-from-the-runway fashion, the 1989 Era saw Taylor at her most chic, and “Style,” with its driving synths and adult lyrics, is tailor-made to match her grown-up glow-up. While the chorus sounds triumphant, with its repeated “We never go out of style” refrain, the full song tells a more complicated story of an on-and-off couple that can’t stay faithful to (or away from) each other. It’s a messy affair, just like a lot of 20-something love stories.
Most Taylor Lyric: “You got that James Dean daydream look in your eye/ And I got that red lip classic thing that you like”
Taylor’s Version Proposal: What if Harry Styles – the alleged slicked-back-hair inspiration behind the top 10 Hot 100 hit – duetted on a 1989 (Taylor’s Version) bonus track? Fans’ heads would explode, yes, but also the dreamy pop vibe just fits Harry’s, well, style perfectly — and imagine a new verse written from his perspective. — K.A.
"Love Story" (Fearless, 2008)
Why It’s Era-Defining: “Love Story,” the first single from Fearless, was one of the earliest signals that Swift’s keen songwriting ability and pop sensibilities had a reach far beyond country music audiences. Released in 2008, “Love Story” spent two weeks atop Country Airplay, and also reached No. 4 on the Hot 100, and was certified 8x multi-platinum by the RIAA. Ultimately, “Love Story” came to define two separate eras in Swift’s career — as in 2021, “Love Story (Taylor’s Version)” served as the introduction to Swift’s process of re-recording her older albums.
Most Taylor Lyric: “This love is difficult, but it’s real/ Don’t be afraid, we’ll make it out of this mess”
Fun Fact: When “Love Story (Taylor’s Version)” reached the pinnacle of the Hot Country Songs chart, the feat put Swift in the company of Dolly Parton, as the second artist to reach No. 1 with original and re-recorded renditions of the same song. (Parton topped the chart with “I Will Always Love You” in 1974 and a second time with an updated recording of the song in 1982.) — J.N.
"August" (Folklore, 2020)
Why It’s Era-Defining: Though the enduring image of the Folklore era is the greyscale starkness of its cover, the album itself was stunningly polychromatic — as perhaps best evinced by the lush gauziness of “August.” With strings and reverb wrapped around one of her coziest melodies and most wistful (and rueful) lyrics, it almost sounds like Swift and Antonoff fantasizing about being an early ’90s shoegaze duo, a sweet dream indeed.
Most Taylor Lyric: “Cancel plans just in case you’d call/ And say, ‘Meet me behind the mall'”
Ideal Live Guest: Let’s go full alt ’90s with it and get Billy Corgan of the Smashing Pumpkins to provide backing vocals — and maybe even some mellotron over the swirling outro. — A.U.
"Clean" (1989, 2014)
Why It’s Era-Defining: A post-breakup palette cleanser akin to Red’s “Begin Again,” the Imogen Heap-featuring “Clean” finds Swift wrapping 1989 with a weary, hard-earned sense of release. The ethereal electronics ensure it fits the rest of the album, but this meditative, metaphoric mood piece also served to remind fans that Swift the singer-songwriter wasn’t going anywhere amidst her blockbuster-pop pivot.
Most Taylor Lyric: “Hung my head as I lost the war / And the sky turned black like a perfect storm”
Screaming Color: An ocherous yellow. — J. Lynch
"I Knew You Were Trouble" (Red, 2012)
Why It’s Era-Defining: For the curly-haired, sparkly dress-wearing Swift, “I Knew You Were Trouble” was a very edgy new twist. It’s mature and even sexy (and so was the music video), something we hadn’t seen from the star before. With this Hot 100 No. 2 hit, Swift proved that she was ready to be taken seriously as an adult, as she continued to excel in her career.
Most Taylor Lyric: “And the saddest fear/ Comes creepin’ in/ That you never loved me/ Or her/ Or anyone/ Or anything.”
Taylor on Taylor: “I think when it’s all over it comes back in flashes, you know? It’s like a kaleidoscope of memories, it just all comes back but he never does,” Swift says in the opening monologue of the single’s music video. “I think that the worst part of it all wasn’t losing him, it was losing me.” — R.A.
"Dear John" (Speak Now, 2010)
Why It’s Era-Defining: Eleven years before we had a 10-minute version of “All Too Well,” the nearly seven-minute “Dear John” stood as Swift’s loftiest post-breakup takedown — and make no mistake, this slow-burning evisceration still smarts all this time later. The way that Swift gives every emotional injustice room to breathe, and time to simmer, makes “Dear John” an almost pummeling listening experience… but her intensity makes the vitriol connect,