The 100 Best Songs of 1969: Staff Picks

But as you'll see, there's still an embarrassment of riches to be had: pop classics, singer-songwriter standards, FM rock perennials, intergalactic side-long jazz odysseys and only-in-'69 oddities all among them. Read on, and get ready to be taken higher. 

100. Zager & Evans, "In the Year 2525 (Exordium & Terminus)" (No. 1, Hot 100)

When Aldrin and Armstrong stepped onto the moon - the signature engineering achievement of the century -- the No. 1 song on Earth was a doomy folk-rocker about planetary death by technology. Rick Evans wrote “2525” in the mid-’60s, but shelved it until he and Denny Zager needed to pad a regular lounge gig. Audiences flipped for the verse-free jeremiad, and the Nebraskan duo released the tune on their own label before it got picked up by RCA. Though they released a few LPs before splitting, Zager & Evans remained the ultimate one-hit wonder: only “2525” reached the chart. But this driving, droning fluke smash still feels like an AM broadcast from a distant world. -- BRAD SHOUP

99. Friends of Distinction, "Grazing in the Grass" (No. 3, Hot 100)

It hadn't even been a year since Hugh Masekela's sauntering jazz instrumental "Grass" had topped the Hot 100 when The Friends of Distinction -- an L.A. vocal quartet discovered by NFL legend Jim Brown -- threw on some rapid-fire lyrics and a whole lot of even-quicker horns, and mowed all the way back to the top five. Not hard to see why: The flower power hits you right smack in the chest on this one, an irresistible soul-pop blast that asks "Can you dig it?" and very much refuses to take no for an answer. -- ANDREW UNTERBERGER

98. Wendy and Bonnie, "Let Yourself Go Another Time" (Did not chart)

Kicking off in medias res with a wild organ solo hurtling toward the stratosphere, "Let Yourself Go Another Time" is an undeservedly obscure folk-pop gem from teenage sister duo Wendy & Bonnie. The San Fran siblings specialized in haunting harmonies with psychedelic flourishes -- and with "Flower" being Wendy and Bonnie's honest-to-God last name, what else could they have done with their lives in the late '60s Bay Area? -- JOE LYNCH

97. Chicago, "Questions 67 and 68" (No. 24, Hot 100)

The title suggests persistent mysticism; the structure implies proggy ambition. But the production was pure pop, and the lyric -- a flirtatious monologue -- predicted the hippie slide down the Maslow Hierarchy. “Questions” was the first single from the band’s debut album; while the former initially scraped to No. 71, the latter was, at one point, the longest-running rock album in Top 200 history. Immaculately recorded by longtime Chicago associate Jim Guercio (who cut his horn-rock teeth producing the Buckinghams and Blood, Sweat & Tears), “Questions” was brassy and optimistic, without a shred of psychedelia. It just needed the right decade: re-released in 1971, it hit the top 30. -- B.S.

96. Mongo Santamaría, "Cloud Nine" (No. 32, Hot 100)

Cuban percussionist Mongo Santamaría was enlisted to play congas on the Temptations' "Cloud Nine" -- one of the best of the string of Whitfield-Strong psychedelic soul firecrackers the group would record around the turn of the decade -- so it was only right that his own band would get to take a crack at the song on his '69 LP Stone Soul. Upping the tempo and layering the bass and percussion until the whirling groove kicks up a Tasmanian Devil level of dust, Santamaría's take on the struggle anthem is even more intoxicating and unnerving than the original, with the two-word shout of the faux-ecstatic title proving the only lyrics necessary. -- A.U.

95. Candi Staton, "I'd Rather Be an Old Man's Sweetheart (Than a Young Man's Fool)" (No. 46, Hot 100)

It’s pretty hard to go wrong with anything coming out of Muscle Shoals in the late 1960s, and soul great Candi Staton’s pragmatic breakout hit is no exception. The FAME studio’s iconic rough-and-tumble sound lays the perfect groundwork for brash lyrics like “You may think I’m silly to love a man twice my age/ But I know from experience girls, sometimes it pays” -- a convincing argument, then and now, shared via the brightest, sassiest soul. -- NATALIE WEINER

94. Joe Cocker, "Feelin' Alright" (No. 33, Hot 100)

Traffic’s 1968 original is great, but what Joe Cocker did -- what Joe Cocker seemed to do to virtually every cover he touched -- is sublime. There's Artie Butler’s groovy piano opening, those urgent backing vocals from no less than Merry Clayton and Brenda Holloway, and Cocker giving you his best raspy, throaty, gutsy performance. In the Traffic version, the song title was a question (“Feelin’ Alright?”), but after Joe Cocker sang it, no one had to ask anymore. -- STEREO WILLIAMS

93. David Axelrod, "The Human Abstract" (Did not chart)

A spacious exemplar of jazz producer, arranger and composer David Axelrod’s singular sound, “The Human Abstract” will be especially familiar to fans of DJ Shadow, who sampled it twice on his 1996 instrumental rap classic Endtroducing…. Undergirded by haunting piano and bass work, the longest track on Axelrod’s second album as an artist -- an esoteric tribute to the poet William Blake, just like his first album -- eventually blossoms into a lush orchestral work, conjuring an expansive, inscrutable kingdom in just five-and-a-half minutes. No surprise, then, that Shadow swiped it for “Midnight in a Perfect World.” -- ROSS SCARANO

92. Billie Jo Spears, "Mr. Walker, It's All Over" (No. 80, Hot 100)

Billie Jo Spears' version of the Tom T. Hall-written "Harper Valley PTA" was released the same week as Jeannie C. Riley's in 1968, but only Riley's version became a hit, eventually topping the Hot 100. Spears would have to wait until the next year for her debut on the chart, with the similarly straight-shooting "Mr. Walker, It's All Over," about a protagonist from Kansas with "a yen to see New York," but who finds her job there as a big-city secretary demeaning enough to send her right back to Garden City. The song's biting response to workplace harassment ("That's a lot of hands a-reachin' out to grab the things that I consider mine") feels just as sharp 50 years later, and the lyrical detail is evocative enough in its Manhattan scene-setting that it feels like an entire Mad Men episode in its three-minute runtime. -- A.U.

91. Three Dog Night, "Easy to Be Hard" (No. 4, Hot 100)

Practically an American standard at this point, covered many times over, “Easy to Be Hard” is a piercing lament for casual callousness from the landmark hippie musical Hair. L.A. rock band Three Dog Night recorded the best-known version for its sophomore release, Suitable for Framing; it peaked at No. 4 on the Hot 100 in September 1969. With a voice strengthened by experience in the Bronx doo-wop group the Rondells, vocalist Chuck Negron climbs from a gentle croon to full-throated belting, still managing to avoid the obvious theatrics of the song’s origin. -- R.S.

90. Nina Simone, "Just Like Tom Thumb's Blues" (Did not chart)

The 1969 album To Love Somebody, mostly consisting of '60s rock covers, was rushed out to capitalize on the success of Nina Simone's '68 live album 'Nuff Said -- but it was far from a thoughtless cash-in, as the singer-songwriter found fascinating new ways into standards from the likes of Leonard Cohen, The Bee Gees and The Beatles. Her rendition of Bob Dylan's Highway 61 Revisited cut "Just Like Tom Thumb's Blues" was a particular revelation, discovering a sympathy in its lyric and a tenderness in its melody -- via an intimate, stripped-down arrangement that almost sounds like it belongs on the third Velvet Underground album -- that makes the original feel brittle by comparison. -- A.U.

89. Cass Elliot, "Make Your Own Kind of Music" (No. 36, Hot 100)

Though just a modest hit, Elliot’s ode to striking out on your own was a crucial evolution in self-referential pop. The year before, Elliot had plain struck out: her debut album stiffed, and she made national news when her three-week Vegas residency closed after a single awful performance. In this light, the sunshine pop of “Make Your Own Kind of Music” (written by Cynthia Weil and Barry Mann) sparkled even more defiantly. In the 21st century, the song became a small-screen touchstone, soundtracking moments both iconic and inspirational. -- B.S.

88. Bob Dylan, "Tonight I'll Be Staying Here With You" (No. 50, Hot 100)

Few likely could've predicted Bob Dylan's reemergence amidst the societal tumult of 1969 as a country balladeer on the sun-soaked Nashville Skyline. But what the songs lacked in timeliness, they made up for in timelessness, none moreso than on the understated "Tonight I'll Be Staying Here With You." Dylan proves a natural fit for country's tendency towards economic wit and strong central lyrical conceits, as he begs over soft sheets of slide guitar for his intended to defenestrate his tools for escape while he shacks up for the night. It's the gentle inverse of the prickly "Don't Think Twice, It's All Right," and feels like the hard-earned night's rest at the end of a long decade's journey for Dylan. -- A.U.

87. Neil Diamond, "Sweet Caroline" (No. 4, Hot 100)

This rousing pop song was Diamond's first top five hit on the Hot 100 (as an artist; he had gotten there previously with a couple of songs he wrote for The Monkees). While he'd go on to have higher-peaking hits on the chart, "Sweet Caroline" has remained Diamond's most sure-fire crowd-pleaser in concert for 50 years. And nobody would dare make a beer run during the surefire singalong, or they'd spill it on the way back to their seat with every arm-thrusting "so good!," "so good!," "so good!" -- PAUL GREIN

86. King Crimson, "21st Century Schizoid Man" (Did not chart)

With a hellish drive to craft something no one had ever heard, prog-rock progenitors King Crimson delivered the heaviest thing to hit late-'60s mainstream music with “21st Century Schizoid Man.” Flanked by a sustained, screeching cacophony and the most grisly pairing of guitar and saxophone imaginable, the collective ventured into unknown territory that blazed a trail spanning generations, from their art-rock contemporaries to the horde of heavy metal bands that followed over the next two decades -- and all the way into the 21st century itself, with Kanye West’s career-defining statement “Power.” -- BRYAN KRESS

85. Booker T. & the M.G.'s, "Time Is Tight" (No. 6, Hot 100)

Written by Booker T. Jones in Paris just before the May 1968 riots began, and used to score the climactic scene of the Jules Dassin drama Up Tight, “Time Is Tight” was released as a single the following year -- and became Booker T and the MGs’ biggest hit since 1962’s “Green Onions.” It’s the sound of a quartet ably demonstrating its equilateral greatness: Jones’ eerie, soulful Hammond organ lines; Steve Cropper’s bristling counterpart guitar; Donald “Duck” Dunn’s minimalist bass grooves and the atomic timekeeping of Al Jackson, one of the decade’s best drummers. -- CHRIS O'LEARY

84. Nick Drake, "River Man" (Did not chart)

“River Man” was cut live in the studio, Nick Drake singing and playing acoustic guitar while a string section swayed around him. In a languid 5/4 time, it's the centerpiece of Drake's debut LP Five Leaves Left and one of his most essential songs -- starring Betty, who prays for the sky to blow away, and the River Man, the god of a material world that Drake felt exiled from. “Oh, how they come and go,” he sings in his low, hypnotically resonant voice. The LP’s back cover has Drake leaning against a wall, smiling as a businessman races past him in a blur. -- C.O.

83. Roberta Flack, "Compared to What" (Did not chart)

Listeners mostly familiar with Roberta Flack from her smash '70s ballads might be surprised by her 1969 debut single, in which she lays Gene McDaniels' pissed-off protest lyric over barbed horns and upright bass, with the confidence and disgust of a hardened veteran. The single failed to make a chart impact -- Flack's true breakout wouldn't come until Clint Eastwood's Play Misty For Me used its album-mate "The First Time Ever I Saw Your Face" in a love scene -- but the song hit the Hot 100 the next year in an electric live jazz version, performed by singer-pianist Les McCann and tenor saxophonist Eddie Harris at the '69 Montreux Jazz Festival. -- A.U.

82. Harry J All Stars, "Liquidator" (Did not chart)

Given the just-in-time ethos of the Jamaican recording industry -- developed to serve a ravenous sound-system culture -- the provenance of “Liquidator” is and will remain cloudy. The most common origin story involves singer/producer Tony Scott selling the germ of a tune called “What Am I to Do” to early reggae entrepreneur Harry Johnson, who had the song recorded as an instrumental by a clutch of session stars. On the strength of its buoyant organ topline, “Liquidator” was a U.K. top ten hit. But it was Aston Barrett’s percolating bassline that had the greatest influence: Stax executive Al Bell made it the foundation of “I’ll Take You There,” a No. 1 hit for the Staple Singers in 1972. -- B.S.

81. B.B. King, "The Thrill Is Gone" (No. 15, Hot 100)

Before “Lucille” was known as the barbed wire-wrapped baseball bat wielded by Negan on the The Walking Dead, it was the name of King’s hollow-bodied Gibson guitar -- an instrument that cried the blues just as vibrantly as B.B. sang them. Although Roy Hawkins, who co-wrote “Thrill” with Rick Darnell, hit No. 6 on Billboard’s R&B chart with it in 1951, King’s version, which paired his plaintive guitar licks with elegant strings, became his signature song and a rare pop hit, reaching No. 15 on the Hot 100. At a time when British acts like Led Zeppelin, John Mayall and The Yardbirds were storming the charts with their interpretations of the genre, King reminded the world that the blues were an American art form. -- FRANK DIGIACOMO

80. Barbara Acklin, "Am I the Same Girl?" (No. 79, Hot 100)

“Soulful Strut” may have been one of the most ubiquitous songs of early 1969, but before it was stripped of its vocal for that Young-Holt Unlimited smash, Acklin originally recorded the track as a love song, with optimistic if wistful lyrics about revisiting a former flame. At the time the instrumental was considerably more popular, but the long legacy of "Same Girl" (from Dusty Springfield to Swing Out Sister) has relied as much on Acklin’s insistent, innocent melody as much as the song’s irresistible groove. -- N.W.

79. Syl Johnson, "Is It Because I'm Black" (No. 68, Hot 100)

A scrappy performer, songwriter and producer from Chicago by way of Mississippi, Syl Johnson had worked with and near some of the biggest names in blues and R&B. But at the end of the ‘60s, with his career and personal life languishing, and reeling from the assassination of Dr. King, Johnson set about recording a deep-soul concept album. The lead single and title track from the project was “Is It Because I’m Black,” a slow-rolling, obsessive rumination on racism and what one is due. Not an obvious candidate for radio play, its searing despair and insomniac groove struck a chord with black listeners, who inundated radio stations with requests. These days, Johnson is most famous for his widely sampled funk singles, but “Black” and its album were a vital precursor to Marvin Gaye’s auteurist ‘70s soul. -- B.S.

78. Tom T. Hall, "Homecoming" (No. 5, Country Songs)

A country musician talks to his father, whom he hasn’t seen in a while. Quite a while. Tom T. Hall only gives the singer’s half of the conversation -- responses are piano and guitar fills, a spin on the garbled adult voices in Charlie Brown cartoons. In a handful of verses, he reveals the singer’s deep self-absorption: he’s missed his mother’s funeral, doesn’t seem too bothered about it, is itching to get on the road again with the girl sleeping in his car. A top five country hit, it’s all tight smiles and small talk -- a homecoming in name only. -- C.O.

77. Serge Gainsbourg & Jane Birkin, "Je t'aime... moi non plus" (No. 58, Hot 100)

Before “Pillow Talk,” “Love to Love You Baby" and "Birthday Cake" -- or Birkin bags -- there was “Je t’aime... moi non plus.” French Renaissance man and pick-up artist Gainsbourg initially wrote the song for film star Brigitte Bardot, and recorded it with her in '67 -- but the single was shelved when the actress’ jealous husband found out about it. After meeting and falling for Birkin (23 years his junior) on a movie set, they re-recorded the song over a yearning organ and strings that would become the norm for ‘70s porn. Gainsbourg called it an “anti-fuck” song, but Birkin’s erotic sighs and simulated orgasm distracted most listeners from the lyrics (even those who spoke French). Denounced by the Vatican and banned by radio in several countries, “Je t’aime" still climbed to No. 58 on the Hot 100 -- a sure sign that, in America, the sexual revolution of the ‘60s had gone pop. -- F.D.

76. Frank Zappa, "Peaches en Regalia" (Did not chart)

Leave it to experimental '60s maestro Frank Zappa to try something completely off-the-wall and make it sound easy. A jam as twisting and unpredictable as the man himself, “Peaches en Regalia” opened the psych mastermind's self-described “movie for your ears” album Hot Rats like it was soundtracking a high speed chase in a classic '70s caper -- always ahead of his time. Zappa toyed around with an easygoing, improvisational quality that belies the tedious perfectionist that he was, and yields the perceptible payoff for staying true to himself. -- B.K.

75. Edwin Starr, "Twenty Five Miles" (No. 6, Hot 100)

"Come on feet, start moving!" Edwin Starr commands at the start of "Twenty Five Miles," playing drill instructor to his own lower extremities. It's necessary motivation, as Starr spends the entirety of his breakout hit convincingly split between his heart and soul refusing to let anything stop him from trudging the titular distance back to his baby, and the rest of his body refusing to do much of anything, at all, ever again. Emboldened by the horns and supportive backup vocals, Starr audibly treks his way to the finish line ("I got nine... eight... seven... six... I got five more miles to go now!"), the suspense becoming almost unbearable. You never hear for sure if he makes it -- but then again, you never technically see Butch Cassidy and the Sundance Kid go down in a hail of bullets, either. -- A.U.

74. Cream, "Badge" (No. 60, Hot 100)

It's best not to search for too much hidden meaning in the abstract lyrics of this Cream classic, given that co-writers Eric Clapton and George Harrison have spoken about the song's slapdash and drunken origins (credit Harrison's Beatles bandmate Ringo Starr with that line about swans), and its cryptic title is merely an inside joke about bad handwriting. But who needs hidden meaning when this song is so cool? With the two legendary guitar gods sharing axe duties and a pounding piano line motoring the groove, this song's fleeting 2:44 run time is always too short. -- KATIE ATKINSON

73. Terry Riley, "A Rainbow in Curved Air" (Did not chart)

The layers of chirping, glistening and trilling synths and organs that comprise electronic composer Terry Riley's gorgeous side-long masterwork "A Rainbow in Curved Air" sound as much like a prediction as a composition, one that would be borne out essentially for the remainder of the 20th century. Of course it would prove incalculably influential on decades of electronic and avant-pop music, from Kraftwerk and Mike Oldfield to Stereolab and Boards of Canada. But the song's most direct impact can still be heard daily on classic-rock radio, via the iconic keyboard intros to The Who's "Won't Get Fooled Again" and "Baba O'Riley" -- the latter even partly named after the composer. -- A.U.

72. Diana Ross & The Supremes, "Someday We'll Be Together" (No. 1, Hot 100)

Originally recorded by the duo Johnny (Bristol) and Jackey (Beavers) and co-written alongside Harvey Fuqua (Tri-Phi Records) in 1961, “Someday We’ll Be Together” was revived in 1969 when Motown Records solicited Bristol to produce a new version for Jr. Walker & The All-Stars. However, Motown head Berry Gordy intercepted the song, and it ended up instead as the The Supremes' final No. 1 single. A sort of farewell to the group's lead singer, Diana Ross -- the only one of the Supremes to actually sing on the recording -- "Someday" presumed a future of risks and opportunities as part of adulthood, and heartbreakingly yearned for a reunion even in the midst of fracture. -- PAMELA BUSTIOS

71. The Kinks, "Arthur" (Did not chart) 

The Kinks sound a little bit like they're talking to their own insecurities when leaders Ray and Dave Davies sing to the titular protagonist of their 1969 concept album, "Arthur, the world's gone and passed you by, don't you know it?" Angry young men now grown, The Kinks struggled to maintain their early popularity in the late '60s, but the sprawling Arthur and its title-track closer have endured as essentials, helped by its despairing narrative turning sympathetic for the rousing outro: "Arthur we read you and understand you/ Arthur we like you and want to help you." That adaptability would suit the Davies bros well, as The Kinks would go on to experience major chart comebacks in both the '70s and '80s. -- A.U.

70. John Lennon, "Cold Turkey" (No. 30, Hot 100)

“This is what I thought of when I was withdrawing from heroin,” said John Lennon about “Cold Turkey,” the second single of his non-Beatles era with Plastic Ono Band. A candid depiction of his addiction in a period when the opioid’s widespread recreational use (especially among rock musicians) led to consequential damages, the song narrates the pain and distress caused by the abrupt reduction of its effects -- ultimately showing more than telling, as a despairing, borderline-feral Lennon spends much of the song's final minute wailing in agony. -- P.B.

69. Steam, "Na Na Hey Hey Kiss Him Goodbye" (No. 1, Hot 100)

As soul-pop chant-along "Na Na Hey Hey Kiss Him Goodbye" was scaling the Hot 100, Mercury Records had an interesting problem: There was no band to capitalize on its success. The song was a throwaway, composed and performed by studio musicians Gary DeCarlo and Dale Frashuer, meant to occupy space on a B-side -- and later shuttled to an A-side to be released under a made-up band name, so as not to reflect poorly on the songwriters. Unfortunately, the thing was just too damn sticky, a rumbling groove of unstoppable bubblegum momentum, eventually resulting in the rare No. 1 hit that no one wanted to take credit for. That the song endures as the eternal soundtrack to ejections or foul-outs in pro sports feels appropriately random. -- A.U.

68. Iron Butterfly, "in-A-Gadda-Da-Vida" (No. 30, Hot 100)

The 17-minute acid-rock rager was presented as a psychedelic tour de force, but with its searing, percussive guitar work -- released ahead of Zeppelin and Sabbath's debut albums -- “In-a-Gadda-Da-Vida” became a key influence on all things metal. It was one of the weirdest songs to receive heavy FM radio play at the time, foretelling hard rock's looming influence over popular music... and the First Church of Springfield a generation later. -- CHRIS PAYNE

67. Blood, Sweat & Tears, "Spinning Wheel" (No. 2, Hot 100)

Safe to say that 1969 was a good year for jazz-rock supercollective Blood, Sweat & Tears, who scored a trio of No. 2 smashes off their self-titled sophomore album, which itself spent seven weeks atop the Billboard 200 and eventually beat The Beatles for the album of the year Grammy. The best of those hits was the stop-start circus funk and Paulie Walnuts-approved homespun wisdom of "Spinning Wheel," a wildly unpredictable jam with a commanding vocal and a Walls of Jericho-worthy effort from the horn section. The song's opening line proved prophetic: Once the calendar turned to 1970, BS&T never had another top 10 hit. -- A.U.

66. Joni Mitchell, "Chelsea Morning" (Did not chart)

A song about the simple joy of waking up to a sun-kissed room might be cloying in the hands of a lesser scribe. But Joni Mitchell brings her New York City apartment to vivid, breathing life with deft turns of phrase ("A song outside my window/ And the traffic wrote the words") and crisp, off-kilter acoustic strumming, largely thanks to her proclivity for unconventional guitar tunings. Hailing from her aptly named second album Clouds, "Chelsea Morning" catches Mitchell in the midst of her breakneck ascent into the songwriting firmament. -- J.L.

65. James Brown, "Give It Up or Turnit a Loose" (No. 15, Hot 100)

The first of an absurd seven top 40 Hot 100 hits that Brown scored in 1969, “Give It Up or Turnit a Loose” is not one for lyrics enthusiasts (or grammarians). Like quite a few of the Godfather’s songs, his vocals boil down to a laundry list of  some of his most mimicked (and sampled) catchphrases and caterwauls, including  “Baaaby!”,  “Huh!”,   “Unnnh!” and “Hey-Hey-Hey-Hey-Heyyyyy!” The reason to listen here is the sweaty, dense, dance-tastic funk laid down by the James Brown Orchestra, whose members included Maceo Parker on tenor saxophone, Alfred “Pee Wee” Ellis on alto sax, Nate Jones on drums, and “Sweet” Charles Sherrell, whose lung-shaking bass playing anchors the song. -- F.D.

64. Motherlode, "When I Die" (No. 18, Hot 100)

For the love of drums, hip-hop has preserved songs and bands that would’ve likely vanished from collective memory, including this short-lived interracial Ontario act. Pop fans from the '60s might remember the stately soul of “When I Die” from when it hit the top 20 in October 1969, the four piece’s only hit (No. 1 in Canada, though!). Listeners of a later generation might know it best for how the late J Dilla flipped it on his final album Donuts, which he largely recorded in the hospital, where he was dying of a rare blood disease and lupus. -- R.S.

63. The 5th Dimension, "Wedding Bell Blues" (No. 1, Hot 100)

Here's a heartfelt torch song that thinks it's a rousing pop song. Or is that the other way around? The song -- which was written by Rock and Roll Hall of Famer Laura Nyro, sung by the criminally underrated Marilyn McCoo and produced by the talented Bones Howe -- works on both levels; no wonder it shot to No. 1 on the Hot 100. No less discerning a pop critic than Morrissey recently released a faithful cover version, with backup vocals by Billie Joe Armstrong. We're with both Marilyn and Moz: Come on, Bill! -- P.G.

62. Sly & the Family Stone, "I Want to Take You Higher" (No. 38, Hot 100)

You know when the plane is accelerating for take off, right before the wheels leave the ground, and it feels like you’re being pressed into your seat, like you’re being pulled down and back ass-first? That moment is where Sly & the Family Stone’s “I Want to Take You Higher” lives; it urges you to elevate but the funk is too heavy, the guitar and bass practically touching the ground, chugging. The fourth single from Stand!, “Higher” peaked at No. 38 on the Hot 100 in June of 1970, following the release of the Woodstock documentary where it featured prominently. Unlike many of the album’s other classics, there’s no pointed societal message here -- the song is primordial. -- R.S.

61. The Upsetters, "Return of Django" (Did not chart)

Striding through the door Desmond Dekker opened, The Upsetters’ “Return of Django” hit No. 5 in the U.K. in late 1969 after its use in a Terry Gilliam-directed Cadburys ad. It was the arrival on the world stage of the producer Lee “Scratch” Perry: the Upsetters were his studio band. “Django,” which started as a rewrite of a Fats Domino single and was named after a spaghetti Western, served as a bouncing transfer station from ska (Val Bennett’s tenor saxophone solo) to reggae (its irresistible bass and drums). -- C.O.

60. Peter, Paul & Mary, "Leaving on a Jet Plane" (No. 1, Hot 100)

If you’ve sat around a campfire -- specifically one during the last week of overnight camp -- you’ve heard this perennial, which begs for someone to bust out an acoustic guitar. The gently spoken lyrics about having to leave someone behind, but hoping they will wait for you while you’re away, tell a story that speaks to our most human qualities, from fear of change to just wanting to be wanted. Originally written and recorded by John Denver, “Leaving on a Jet Plane” became Peter, Paul & Mary’s biggest Hot 100 hit. Appropriately for its title, it also became the trio’s last before disbanding. -- LYNDSEY HAVENS

59. Led Zeppelin, "Good Times Bad Times" (No. 80, Hot 100)

Before becoming famous for tales about mysticism and Vikings, Led Zeppelin were all about that good ol’ rock n’ roll. “Good Times Bad Times,” which served as the band’s debut single and opening track of its self-titled album, was a hell of an introduction to each member’s charm. Jimmy Page’s shrieking guitar mimicked Robert Plant’s aching tone as he rambled on about loneliness. John Paul Jones kept the bassline steady, while John Bonham pounded on those drums like the band’s livelihood depended on it. Luckily they turned out just fine for the next decade. -- BIANCA GRACIE

58. Eddie Bo, "The Hook & Sling" (No. 73, Hot 100)

The youthful giddiness of the funky “Hook & Sling” belied the long career of its mastermind: Eddie Bo had spent the greater part of two decades as a bandleader, recording artist, and songwriter. At the same time as his New Orleanian peers Lee Dorsey and the Meters, Eddie was threading R&B through the particular snap and strut of his hometown. The result was a left-field delight -- a pared-down groove with Eddie’s yelpy rap and a horn chart out of nowhere -- and a modest national hit. As funky as the backbeat was, though, the true hook was the words Eddie slung: his exhortations have been sampled on everything from "Mama Said Knock You Out" to "SexyBack" to "Lost in the World." -- B.S.

57. The Temptations, "I Can't Get Next to You" (No. 1, Hot 100)

There was nary a crease in sight when the meticulously ironed-out "My Girl" took the Temptations to No. 1 in 1966, but with "I Can't Get Next to You," the Motown vocal pros proved they could get raw, raucous and funky AF and still top the Hot 100 (it actually ruled a week longer than "My Girl"). Willing to let perfection fall by the wayside in pursuit of a dirty Funk Brothers groove and some scorching vocal runs, the Temps' potent mixture of rock, psych and R&B on "Can't" demonstrated they could, in fact, readily adapt to the rapidly changing times. -- J.L.

56. Tommy James and the Shondells, "Crystal Blue Persuasion" (No. 2, Hot 100)

Few of the many utopian pop songs from the late '60s are powerful enough to survive to dramatically less optimistic times, but Tommy James' "Crystal Blue Persuasion" indeed remains pretty convincing a half-century later. A mix of fluttering flamenco guitar, free-roaming bass, and just enough bongo and conga to avoid being totally obnoxious, "Persuasion" still mostly gets by on the sighing ecstasy of James' multi-tracked vocal, prophesying, "A new day is coming/ People are changing/ Ain't it beautiful?" It's the sound of a guy blissfully unaware that he's about to pass on Woodstock, based on his secretary's undersell of "There's this pig farmer in upstate New York that wants you to play in his field." -- A.U.

55. Pharoah Sanders, "The Creator Has a Master Plan" (Did not chart)

Free jazz epics that covered one (or more!) LP sides were standard fare throughout the ‘60s; everyone from Coleman to Coltrane recorded them. For his second Impulse effort, tenor saxophonist Pharoah Sanders -- featured on many of Coltrane’s final recordings -- honored the totality of his late bandmate’s legacy with “The Creator Has a Master Plan,” a sprawling landscape of serene grooves abutting Leon Thomas’ vocal gymnastics and Sanders’ overdriven skronk. A crossover success for its rolling blend of spirituality and intensity, “Master Plan” landed Sanders on the Billboard 200 for the first time, and established him as an icon of what would become acid jazz. -- B.S.

54. Johnny Cash, "A Boy Named Sue" (No. 2, Hot 100)

No one could tell a musical story better than Johnny Cash, and the Man in Black fully embodies the titular boy named Sue in this offbeat country gem. Thanks to cheeky lyrics penned by children's author Shel Silverstein (The Giving Tree, Where the Sidewalk Ends), Cash delivers the musical equivalent of a stand-up comedy routine (with a twist ending!) in his laugh-out-loud performance recorded at San Quentin State Prison. And Cash laughed his way all the way to his biggest hit ever on the Hot 100, with "Sue" peaking at No. 2 in the late summer. -- K.A.

53. The Rolling Stones, "Honky Tonk Women" (No. 1, Hot 100)

No bad song has ever kicked off with cowbell, and you can be damn sure The Rolling Stones weren't about to have the first. Introducing the brand of swampy soul-rock swagger the band would fully feast on in the decade to come, "Honky Tonk Women" proved a hell of a pit stop between 1968's Beggars Banquet and the next December's Let It Bleed, scoring the band their first No. 1 in three years, and introducing "She blew my nose and then she blew my mind" to the all-time rock vernacular. Originally a country song, the Stones took "Honky" back to Nashville for its silly Bleed redo as "Country Honk," featuring the Brian Wilson-worthy audio gag of kicking the song off with a car honking. It was still pretty good. -- A.U.

52. Thunderclap Newman, "Something in the Air" (No. 37, Hot 100)

Thunderclap Newman was named after their pianist, a Pete Townshend acquaintance, and Townshend produced and played bass on “Something In the Air,” the group's only hit. A gorgeous, strange and desperate call for an uprising, with its staircase-climb key changes and barrelhouse piano solo, it held the U.K. No. 1 slot for three weeks in summer 1969, while scraping the top 40 in the U.S. “We have got to get it together... now,” drummer Speedy Keen sang, sounding as if it was already too late. Decades later, “Something in the Air” soundtracked a TV ad -- the revolution had become one of faster mobile phone service. -- C.O.

51. The Beatles, "Don't Let Me Down" (No. 35, Hot 100)

This heart-wrenching track written by Paul McCartney and John Lennon is one of the band’s most underrated. “I’m in love for the first time/ Don’t you know it’s gonna last,” McCartney, Lennon and George Harrison sing, perfectly capturing the feeling of falling hard -- and hoping, perhaps naively, that it’s forever. By the end of the song, the three sing with such desperation that it makes any listener want to sit up straighter, be better. "Don't Let Me Down" is commonly thought of as Lennon's plea to Yoko Ono, but considering the song was recorded during the rocky sessions for Let It Be -- released in 1970 as The Beatles' last studio album -- it could just as well have been a plea to one another to keep a good thing going. -- L.H.

50. Dionne Warwick, "I'll Never Fall in Love Again" (No. 6, Hot 100)

“I’ll Never Fall In Love Again,” a Burt Bacharach/Hal David composition for the musical Promises, Promises ruled a significant chunk of 1969: Bacharach himself, Bobbie Gentry and Johnny Mathis all took mildly successful swings at the deceptively upbeat song over the course of the year. But it was Dionne Warwick’s bossa nova-inflected version that eventually reached no. 6 on the Hot 100 -- her final top ten hit for nearly a half-decade. Rarely has total romantic cynicism (“What do you get when you kiss a guy/ You get enough germs to catch pneumonia”) sounded so lilting and sweet. -- N.W.

49. William Bell, "I Forgot to Be Your Lover" (No. 45, Hot 100)

From the opening guitar lick, this unabashedly seductive single showcases William Bell at his crooner best. “Lover” comes from the more delicate side of Stax, with stripped-down arrangements swathed in velvety yet subtle strings -- the result is a song that sounds almost contemporary, much closer to the kind of Dap-Kings-style revivalism that’s become popular in the 21st century than something stuck in 1969. -- N.W.

48. Donovan, "Altantis" (No. 7, Hot 100)

After Donovan delivers a mystical monologue about the fictitious antediluvian city of Atlantis, a pummeling drum roll at the 1:48 mark floods the ear like a tidal wave wiping that mythological city off the map. "Atlantis" is a swirling sing-along of clanging piano, ecstatic ab-lids and hypnotic harmonies that touches on ancient gods, generational gaps and a love that's just out of reach. The lyrics don't make a whole hell of a lot of sense, but with Donovan imbuing them with religious reverence, this is five minutes of borderline nonsense that cuts deep. Hail, Atlantis. -- J.L.

47. Dusty Springfield, "Breakfast in Bed" (No. 91, Hot 100)

Its reputation established only after the fact, Dusty in Memphis was perhaps the high-water mark for a white pop artist working in a black musical idiom. While the nostalgic joy of 1968 single “Son of a Preacher Man” was the hit, other-woman anthem “Breakfast in Bed” was the fullest demonstration of Springfield’s powers. Like an A-lister tearing into a juicy monologue, Dusty effortlessly traverses empathy, seduction, despair and wistfulness in the course of three minutes. Unlike its thematic sibling “Angel of the Morning,” “Breakfast” offers hard choices, not defiant ones, and its combination of wisdom and discretion coded it as a queer text to those with ears to hear. -- B.S.

46. Creedence Clearwater Revival, "Proud Mary" (No. 2, Hot 100)

CCR’s first of nine top 10 Billboard Hot 100 singles (and five No. 2s!) was a gift that kept on giving to pop music -- and culture -- for years to come. While the jaunty circular guitar riff of the original recording sonically replicates the narrator’s “rollin’ on the river” escape from that Yippie villain “The Man,” the John Fogerty-written classic proved highly adaptable. Ike and Tina Turner performed it as a long-fused R&B firecracker -- with horns -- and got their biggest Hot 100 (No. 4) in 1971, while Elvis incorporated into his ‘70s live shows, Leonard Nimoy butchered it on his 1970 album The New World of Leonard Nimoy, and the song became a Vegas-style staple on corporate-sponsored TV variety shows in the 1970s, "The Man" proving forever inescapable. -- F.D.

45. The Guess Who, "These Eyes" (No. 6, Hot 100)

Can't forget about The Guess Who when discussing the biggest breakout bands of 1969 -- the Canadian blue-eyed soulsters scored three top 25 hits in three tries in '69, with a fourth on the way. The best of the bunch was "These Eyes," gliding in on an electric piano hook so smooth you'd never guess the song's emotional stakes would get above a 7. But singer Burton Cummings goes altogether off the scale on the chorus, which modulates up twice -- and that's just the warmup for the real climax, which reaches such a fever pitch you'd swear "These eyes have seen a lot of loves, but they're never going to see another one like I had with you" was the English translation to the final aria in Madame Butterfly. The fact that Michael Cera's character chooses this song for his impromptu sing-for-your-life performance is the secret funniest part of Superbad. -- A.U.

44. Laura Nyro, "Save the Country" (Did not chart)

Despite being best remembered as a songwriter to the stars, the late Laura Nyro really had a singular voice, a piercing birdsong with the rare ability to grow more powerful as it got more delicate, and vice versa: When she sings a chorus like "Save the people/ Save the children/ Save the country," she sounds both like a plucky 12-year-old handing out pamphlets on a street corner and a true prophet, able to articulate truths not known to most. There was a single version released of this New York Tendaberry album cut, but the buffed-up arrangement just distracts; you're far better off with just Nyro, her piano, and the forever-fluctuating dynamics of Vietnam-era America. -- A.U.

43. Blind Faith, "Can't Find My Way Home" (Did not chart)

The most successful track from the only album by British supergroup Blind Faith -- featuring Steve Winwood, Ginger Baker, Eric Clapton and Ric Grech -- "Can't Find My Way Home" is ostensibly a lament about the navigational difficulties experienced after a drunken night out. But the track is more deeply a parable about the double-edged sword of 1969 itself, when the counterculture promises of personal freedom and social revolution devolved into a collective sense of hazy disorientation. Baker gently keeps the beat, while Clapton's guitar work forecasts the Celtic influence and acoustic delicacy of Led Zeppelin's III, out the following year. -- KATIE BAIN

42. The Band, "Up on Cripple Creek" (No. 25, Hot 100)

If not the best love song about betting on horses and getting stoned to Spike Jones, then certainly the funkiest. "Up on Cripple Creek" was The Band's biggest chart hit, and it's not hard to understand why: While most of their other best-known songs take on a near-gospel stateliness, "Up on Cripple Creek" just gets kinda down and dirty over a slowly swaggering organ shuffle, less a sinner's prayer than a drunkard's dream. The storytelling is straightforward and brilliant; not much is stated but all is understood, down to the surprisingly necessary yodeling breakdown at the end. -- A.U.

41. Desmond Dekker and the Aces, "Israelites" (No. 9, Hot 100)

A classic for its opening line alone, which Desmond Dekker sings with ominous authority. Among the first Jamaican-produced international reggae hits (UK #1, Hot 100 #9), “Israelites” is the culmination of Dekker’s work with producer Leslie Kong -- conversing rhythms on guitar and percussion; a restless bassline; the Aces’ harmonies. If Dekker’s U.S./U.K. audience mostly found him incomprehensible and was happy just to dance to him, he said “Israelites” was a song for Jamaica, of “how we were all downtrodden, just like the Israelites who Moses led to the promised land. I was telling people not to give up as things will get better.” Or as he sang, “after a storm, there must be a calm.” -- C.O.

40. Jefferson Airplane, "Volunteers" (No. 65, Hot 100)

The fury of the Woodstock generation boils over on "Volunteers," a fiery psych-blues manifesto against the Vietnam War. Part CCR racket, part Hair soundtrack maximalism, Jefferson Airplane's most boisterous hit proved San Francisco hippies could rock righteously along with all the flower power -- and at a conspicuously short 2:03, cut against the grain of the era's ever-increasing bloat. -- C.P.

39. Harry Nilsson, "Everybody's Talkin'" (No. 6, Hot 100)

One of his generation’s most distinct voices and idiosyncratic pop songwriters is also one of the era’s more underappreciated interpreters. Harry Nilsson's take on this 1967 lament by Fred Neil became the unofficial theme for Midnight Cowboy, and through that seminal film became a monster hit, his first top 10 on the Hot 100. Nilsson’s vocal is plaintive and wry while the string-heavy arrangement is sweeping and heartbreaking, and the song’s lyrics were relatable for all those who wander -- and anyone tuning out empty commentary on who they are or where they’re going. -- S.W.

38. The Allman Brothers Band, "Whipping Post" (Did not chart)

The first single from The Allman Brothers Band's 1969 eponymous debut album, "Whipping Post" thrust southern rock into mainstream consciousness and helped pave the way for acts like Lynyrd Skynyrd and The Marshall Tucker Band. From its simmering opening guitar riff, the song is all swagger and existential turmoil, with subsequent live versions of the classic wailer taking the psychedelically leaning jam band mentality forged years earlier by The Grateful Dead, and giving it the full sound and fury southern gothic treatment. -- K.B. 

37. Can, "Yoo Doo Right" (Did not chart)

This band of German instrumentalists quietly changed the course of avant-rock in the '70s after the addition of Japanese singer Damo Suzuki, but on Can's 1969 debut Monster Movie -- presided over by mumbling-then-manic American vocalist Malcolm Mooney -- at least one song exemplifies the mesmerizing, motorik groove they would soon master. That tune, album closer "You Doo Right," is 20 minutes of hypnotic repetition that sounds like the self-loathing, desperate cousin of the Velvet Underground's "Sister Ray." And if it 20 minutes sounds long, just keep in mind the studio cut was edited down from a cataclysmic six-hour session. -- J.L.

36. Frank Sinatra, "My Way" (No. 27, Hot 100)

An anthem for the Me Generation, delivered by the greatest entertainer of the Greatest Generation. Sinatra later came to snark "My Way" as self-indulgent, but that didn't stop the grandiose ballad from becoming his signature song, after numerous fallouts and comebacks over thirty years in show business. The words came from Sinatra's friend Paul Anka and when Ol' Blue Eyes let each syllable ring out with his usual panache, survivors of the 20th century's first half earned an overdue marching song: "To say the things he truly feels/ And not the words of one who kneels/ The record shows, I took the blows/ And did it my way." -- C.P.

35. Sly and the Family Stone, "Hot Fun in the Summertime" (No. 2, Hot 100)

Sly and Co. had become one of the biggest acts in music by 1969, and the funk collective delivered two indelible non-album singles that year. “Hot Fun in the Summertime” would hit No. 2 on the Hot 100 -- the epic "Thank You (Falettinme Be Mice Elf Agin)” would be released near the end of the year, and top the chart in 1970 -- and the breezy pop hit belied how effortlessly Sly could jump from gutsy to swaying. An anthem that epitomizes its era, but endures decades later because everyone can relate to having a good time on a hot day: It will always feel like summer. -- S.W.

34. Aretha Franklin, "The Weight" (No. 19, Hot 100)

Despite growing into one of the best-remembered songs of the late '60s, The Band's original "The Weight" failed to make a significant Hot 100 impact in 1968, peaking at No. 63. It was a wrong that the Queen of Soul saw fit to correct with her own undeniable cover version a year later. With its boomeranging guitar and menacing bass, Aretha's rendition tightens the screws on the song's lurching groove a little, while her effortlessly soaring vocal pushes her levels noticeably into the red, more powerful for its obvious sonic fraying. Justice was served that March, as Franklin carried "The Weight" into the top 20. -- A.U.

33. The Who, "We're Not Gonna Take It" (Did not chart)

The Who faced a slew of obstacles as they approached the final act of their unprecedented rock opera Tommy. They had to bring a complex narrative about a "deaf, dumb and blind" messianic figure to a satisfying conclusion, while composing an enthralling finale that could punctuate their cinematic live show as a reliable closer, and developing a catchy yet thematically relevant rallying cry that would galvanize audiences (while inviting some introspection for the increasingly disillusioned masses). Tall order, but the quartet came out triumphant with “We’re Not Gonna Take It,” a crowning achievement of '60s rock songwriting that accomplishes what it needs in service of the album while building itself into a timeless epic all its own -- and even spinning a top 20 hit out of its outro portion alone a year later. -- B.K.

32. Neil Young, "Down by the River" (Did not chart)

As the legend goes, Neil Young was in bed delirious with fever at his Topanga Canyon outpost when inspiration struck for "Down By the River." Taken from Everybody Knows This Is Nowhere, Young's 1969 album with Crazy Horse, the track is a mesmeric nine-minute slow burn, telling the story of an apparently jealous lover and the woman he shot dead. "Be on my side, I'll be on your side; together we may get away," Young sings, highlighting the possibilities of the social revolution then happening in Topanga and beyond. "This much madness is too much sorrow; it's impossible to make it today," he then follows with, in two contrasting lines summing up the cultural fever dream of the late '60s. -- K.B.

31. Fairport Convention, "Who Knows Where the Time Goes?" (Did not chart)

The three albums the folk-rock band Fairport Convention released in 1969 are among the most sublime music ever recorded in Britain. The tower atop those peaks is the ballad “Who Knows Where the Time Goes?” from Unhalfbricking, written and sung by Sandy Denny (Judy Collins already had covered it, using Denny’s original demo). Sounding as old as Chaucer, it’s also deeply woven into its time -- Richard Thompson’s lead guitar, the jazz-influenced chord progressions. Denny, who died in 1978 at age 31 from brain injuries after falling, sings as if she’s standing outside of time, knowing that her song will immortalize her. -- C.O.

30. The Meters, "Cissy Strut" (No. 23, Hot 100)

Exporting the lackadaisical funk of New Orleans in full is near impossible -- something about a rolling snare just sounds different when you’re at the very bottom of the Mississippi Delta. But Zigaboo Modeliste, the singular drummer behind the Meters, along with his compatriots George Porter, Jr., Art Neville and Leo Nocentelli, were more than up to the task as they proved with this timeless instrumental, which marked the group's biggest Hot 100 hit. To listen to "Strut" and remain still might be a sign that you’re beyond hope, at least as far as grooves are concerned. -- N.W.

29. MC5, "Kick Out the Jams" (No. 82, Hot 100)

It’s hard to pinpoint punk’s “birth” -- was it in the early '60s garage bands, or with the late '50s heavy blues guitarists? Or was it when this gaggle of White Panther-affiliated Detroit radicals released this grimy single that opened with a profane call to arms? The MC5 were about as dangerous as any band in the late 60s, and “Kick Out the Jams” -- with its ramshackle urgency and “Fuck you” spirit (and iconic F-bomb-dropping lead-in) -- flew in the face of dying hippie sentiment, while setting the stage for punk’s righteous rebellion. A record of its time, and so far ahead of it. --S.W.

28. Toots & the Maytals, "54-46 Was My Number" (Did not chart)

It’s pretty wild to think that a stint in jail sparked the spread of one of the most influential genres of the 20th century's back half. “54-46 Was My Number,” inspired by Toots Hibbert’s 18-month term following his arrest for weed possession, became the band’s biggest international hit, helping to introduce the world beyond Jamaica to ska. From Hibbert’s pleas of his innocence, that groovy melody and the passionate call-and-response, the song held a sense of defiance that later became the basis of not just what would later transform into reggae music, but its cultural movement as a whole. -- B.G.

27. Peggy Lee, "Is That All There Is?" (No. 11, Hot 100)

“I remember when I was a little girl, our house caught on fire…” Sounds like the beginning of a great Twitter thread, but the fantastically jaded spoken-word classic -- inspired by a 19th century short story, post-Nazi Germany and Kurt Weill -- was perhaps 1969’s most unlikely pop hit, topping the Adult Contemporary chart. Ending with its narrator lamenting her inevitably unimpressive death from the other side, "Is That All There Is?" speaks to the decade-end’s wartime nihilism, and maybe the fact that current ennui isn’t as unprecedented as it might sometimes feel. -- N.W.

26. Santana, "Soul Sacrifice" (Did not chart)

Few performances embody a time and a place so specifically as Santana’s “Soul Sacrifice” -- included on the band’s debut album, but immortalized in the group’s Woodstock performance. With a sleeveless Santana playing soul guitar backed by a cadre of Latin percussionists, it wasn’t just that “Soul Sacrifice” was an instrumental track (still an anomaly for rock at the time), but that it marked the first time that Latin percussion had been fused with rock on a major scale. The inclusion of Santana’s performance in the Woodstock documentary would propel the band’s ascent to fame. However, that day in '69, Carlos Santana’s mind was on how he'd found himself onstage far sooner than anticipated, right after taking hallucinogens from his friend Jerry Garcia. "Maybe an hour and a half, two hours after I took it, someone comes over and he says, ‘If you don't go on right now, you're not going to play at all,'" he recently recalled to Billboard. "The only thing that I remember is praying... 'God, please help me. Please help me stay in tune and on time.'” -- LEILA COBO

25. The Stooges, "I Wanna Be Your Dog" (Did not chart)

What originated as a sleazy pick-up line ended up being a defining record, one that helped pave the jagged road for the punk-rock era. A youthful Iggy Pop, messed up on whatever he was taking at the time, just had one simple request: “I want you here.” His pleas are more uncomfortable than seductive, with Ron Asheton’s fuzzy guitar riff filling the void of Pop’s empty mind. And that sleigh bell jingling throughout turns almost sinister, sticking with you long after the song is over -- like a one-night stand you can’t get rid of the morning after the come down. -- B.G.

24. The Foundations, "Build Me Up Buttercup" (No. 3, Hot 100)

"Build Me Up Buttercup,” on which The Foundations’ Colin Young sings of being stood up and waiting for the phone to ring time and time again, may actually be the first song to chronicle the feeling of being ghosted. But despite its crushing lyrics, the uptempo production, ecstatic backing vocals and life-affirming horns have allowed this song to remain a crowd-pleasing wedding and karaoke staple. And even with the advent of texting and dating apps, the lyrics hold up; only now, instead of waiting for a call, Young would be watching the three iMessage text dots come and go with no response. -- L.H.

23. Stevie Wonder, "My Cherie Amour" (No. 4, Hot 100)

In the years following his breakthrough as The 12 Year Old Genius in 1963, Motown had been slow to give “Little Stevie” the reins to his own career. Having studied songwriters and producers at the label extensively, and having started to pen his own hits alongside collaborators like Sylvia Moy, Stevie was growing by leaps and bounds. This elegant pop ballad would become one of his most enduring moments, a beautifully innocent ode to young love, the song hit No. 4. Today, it feels like a bridge from early Stevie’s lyrical innocence to latter Stevie’s creative supremacy. -- S.W.

22. Miles Davis, "In a Silent Way" (Did not chart)

The Side B of Miles Davis’ extraordinary leap into electronic sounds is initially as peaceful as waking up. His trumpet playing is languid and serene; John MacLaughlin’s electric guitar is tentative but curious (Davis at one point instructed him to play like he didn’t know how); Chick Corea’s electric piano is like jewelry, glittering and rare. And then it breaks open into the “It’s About That Time” portion, able-bodied and enriched by the energy-saving opening. Even as In a Silent Way became one of Davis’s best selling albums, critics were divided broadly into two camps: rock heads loved it, while jazz enthusiasts found it to be a troubling betrayal of everything the maestro had previously created. In 2019, you can hear the roots of ambient, of fusion, of anything that sounds iconoclastic and otherworldly. -- R.S.

21. The Velvet Underground, "Pale Blue Eyes" (Did not chart)

Leave it to Lou Reed to write one of the most soul-shattering ballads of the rock era and make it about an adulterous liaison. A soft Hammond organ provides a gentle gospel undercurrent to this highlight from the experimental outfit's softer third album, consecrating Reed's quietly devastating ode to love inextricably linked to lust. "It was good what we did yesterday/ And I'd do it once again/ The fact that you are married/ Only proves you're my best friend" isn't exactly a Hallmark card message, but its naked realism -- and the sadness in Reed's voice as the words barely escape his lips -- will stick with you a helluva lot longer than much sweeter sentiments. -- J.L.

20. Spiral Starecase, "More Today Than Yesterday" (No. 12, Hot 100)

Proof that 19th century French poetry always sounds better over some goddamn horns, Sacramento pop-rock purveyors swiped the gist of Rosemonde Gérard's best-known couplet from her 1889 ode "L'éternelle Chanson" and spun it into AM gold 80 years later. With its piano pounding, drum bashing and trumpet blazing, "More Today Than Yesterday" moves like a grinning juggernaut, a love song with its head so firmly in the clouds that it thoughtlessly bulldozes anything in its path down on Earth. But the vocal earns the song its delirious brashness, with singer-songwriter Pat Upton impassioned just to the brink of cloying as he delivers one of many brilliantly concise K.O. punches right to the ticker: "And if all my dreams come true/ I'll be spending time with you." -- A.U.

19. Jimmy Cliff, "Many Rivers to Cross" (Did not chart, Hot 100)

As transcendent as anything that Marvin Gaye or Curtis Mayfield would land on the charts in the ‘60s and ‘70s, Jimmy Cliff wrote "Many Rivers to Cross" out of frustration when, after moving to the United Kingdom to build on the success he’d initially found in Jamaica, his career floundered. (Hence, a reggae song that mentions “the white cliffs of Dover.”) His lyrics reflect his dispirited state at the time (“I’ve been licked, washed up for years”), but Cliff’s sweet, defiant tenor -- backed by a church organ and a female choir -- transform the song into a stirring spiritual that he shall overcome. And he did: In 1972, “Many Rivers to Cross” was included on the soundtrack to the cult film The Harder They Come, which starred Cliff as a Jamaican outlaw and featured five more of his songs. The classic soundtrack played a major role in popularizing reggae in the United States, contributing to Cliff’s status as one of the genre’s living legends. -- F.D.

18. Simon & Garfunkel, "The Boxer" (No. 7, Hot 100)

“The Boxer,” lead single off Simon & Garfunkel’s final studio album Bridge Over Troubled Water, signaled the beginning of the end for the hitmaking duo. At the time it was written, Simon spoke about feeling as if he had to fight against unfair criticism the duo had started to receive ("Everybody's beating me up... I'm going to go away if you don't stop"). As such, the song -- which has been covered by Bob Dylan, Mumford & Sons and countless others -- unfolds as a first-person account of the rise and fall of Simon & Garfunkel through Simon’s eyes, and also a third-person story of a boxer ready to hang up their gloves. The lyrical see-saw between acceptance and resistance is just as potent today, best heard on the line: “I am leaving, I am leaving/ But the fighter still remains.” Walking away doesn’t mean you have any less bite; in the end, it makes you that much stronger. -- L.H.

17. Nina Simone, "To Be Young, Gifted and Black" (No. 76, Hot 100)

She wrote the song as a tribute to Lorraine Hansberry. The famed author of A Raisin In the Sun died in 1965, and Nina Simone wanted to write a song that inspired the greatness in young Black people who’d been told by society they did not matter. Poet Weldon Irvine was enlisted to help with the song's lyrics, but he struggled coming up with them -- until he had an epiphany while sitting at a stoplight in Manhattan, en route to pick up a friend from out of town, and ended up scribbling them on a cocktail napkin. “A whole bunch of irate taxi drivers were leaning on their horns," Irvine recalled to journalist Oliver Wang. "I wrote it, put it in the glove compartment, picked up the girl, and didn't look at it until she got back on the bus to go home." That scribbling would become a classic song, covered by everyone from Aretha Franklin to Donny Hathaway to…Elton John. -- S.W.

16. The 5th Dimension, "Aquarius/Let the Sunshine In" (No. 1, Hot 100)

Hair’s impact on American culture was absolutely massive, both in the musical’s visual language and its compositions. Pop singers and groups were mining hits from its book for years: an ongoing demonstration that counter- and monoculture could cohabitate easily. The biggest hit of all was The 5th Dimension’s medley of Hair’s alpha and omega. The five-piece vocal group had garnered notice as cheery, game interpreters of top songwriters like Laura Nyro and Jimmy Webb, but “Aquarius” -- perfectly pitched between easy-listening and eeriness -- took them to the next level. It was their first No. 1, and the apotheosis of the Dimension’s vocal abilities, running the gamut from crystalline to gutbucket. A marvel of production (two key changes rammed together, Vegas vocals merged with an L.A. backing track), the two-parter won record of the year at the 1970 Grammys, and it remains a monolith of flower-power optimism. -- B.S.

15. The Isley Brothers, "It's Your Thing" (No. 2, Hot 100)

Funk was still kind of new as a genre when the Isley Brothers started gettin’ stank in the late 60s. But as the group was beginning to expand both sonically and in terms of personnel (brother Ernie Isley makes his first appearance here -- on bass, not as a guitarist -- though he wouldn’t officially join the band until 1972), they weren’t afraid to move with the times, or to stay ahead of them. On "Thing," the Isleys showed they could out-funk almost anybody, and the result was both a middle finger to their old label (Motown) and a bold testament to individuality. -- S.W.

14. Glen Campbell, "Galveston" (No. 4, Hot 100)

“It’s about a guy who’s caught up in something he doesn’t understand and would rather be somewhere else,” said Jimmy Webb about his “Galveston” in 2010, originally sung by Don Ho and taken to the top of the country charts by Glen Campbell in 1969. Campbell’s recording worked both sides of the Vietnam divide. There’s Al DeLory’s Fourth of July arrangement (Webb said he thought the song should go at a slower tempo) and a stoicism in Campbell’s verse phrasings: a soldier’s daydreaming of home while polishing his rifle. But when Campbell sings the climactic “Galveston,” it’s the voice of a weeping kid who’s terrified of dying. It condemns the war as well as anything Country Joe and the Fish did. -- C.O.

13. The Archies, "Sugar, Sugar" (No. 1, Hot 100)

As the decade came to a close, rock music had moved well past its teenybopper roots: While the nation’s teens and young adults had turned their attention to the happenings in San Francisco, their younger siblings got hooked on the stickier stuff. A reaction to the portentousness of the new youth music, bubblegum was cheery, simplistic, and ruthlessly catchy -- and since it was written and recorded by studio musicians, it didn’t even need real bands. The Archies were the apex of this approach: summoned to televisual life by Don Kirshner after The Monkees unceremoniously dumped his songwriting concern. Written by living legend Jeff Barry and up-and-comer Andy Kim, the midtempo, candy-obsessed “Sugar, Sugar” was a lilting, remorseless hook machine. Fake-band vet Ron Dante (of the Cuff Links and various commercial campaigns) sang the lead. The song had to be handed to DJs with the label missing, but its cynical sweetness spread. And so the biggest single in the Year of Woodstock belonged to cartoon characters. -- B.S.

12. Elvis Presley, "Suspicious Minds" (No. 1, Hot 100)

Elvis Presley’s emotive, audibly weeping vocals are at the heart of his 1969 chart topper “Suspicious Minds,” about a relationship filled with mistrust. A huge hit for the King and his last No. 1 on Billboard’s Hot 100, “Suspicious Minds” helped revive Presley's music career following years of acting, an appropriate fade-back-in powered by a song with one of the greatest fake endings in rock history. Originally recorded by Mark James, Presley released the tune several months after his ’68 Comeback Special, and it remains a favorite in Presley’s catalog, subsequently covered by Fine Young Cannibals, Phish, Dwight Yoakam, and Waylon Jennings and Jessi Colter. -- ANNIE REUTER

11. Led Zeppelin, "Whole Lotta Love" (No. 4, Hot 100)

Of all the riffs in Led Zeppelin’s fabled catalog, few rock as hard or as immediately as the three-chord pattern guitarist Jimmy Page strung together for “Whole Lotta Love." Enormous, jagged and menacing, the song revs into motion with the muscle and madness of a runaway truck, while a metal slide adds to the spellbinding fervor. But just as memorable are the song’s lewd lyrics, with Robert Plant shrieking increasingly dirty innuendos (“I wanna be your backdoor man!”) that reach a dizzy, uh, climax a quarter of the way in. Despite later controversy -- striking lyrical similarities to Muddy Waters’ "You Need Love" led to a lawsuit against Led Zeppelin -- “Whole Lotta Love,” in all its horny glory, became the band’s biggest U.S. chart hit and only top 10 single, reaching No. 4 on the Hot 100 in January 1970, and cementing the group as rock legends for eternity. -- TATIANA CIRISANO

10. The Beatles, Abbey Road Medley (Did not chart)

With their impending dissolution inching closer, The Beatles called their shot and combined forces in the studio for one last round, eschewing a neat and tidy ending for the sprawling medley at the close of Abbey Road. Initially pieced together from scraps of older sessions and loose ideas, the set's Side B feels like a stroll through the biggest band in the world’s brief yet storied career; there’s the quirky McCartney beats (particularly the saloon-style ditty on “You Never Give Me Your Money”), Lennon’s eccentric lyricism (“Mean Mr. Mustard”/”Polythene Pam”) and both the searing rockers ("She Came in Through the Bathroom Window") and the tender, uplifting balladry that served as the band’s foundation (“Golden Slumbers”). The Fab Four save the best for last on “The End” in which these undisputed all-time greats come together to give the masses what they’ve always wanted: There’s the Ringo drum solo, the triumvirate trading guitar licks and the parting couplet that distilled the entire Beatles phenomenon into one philosophy: “In the end, the love you take is equal to the love you make.” -- B.K.

9. Bobbie Gentry, "Fancy" (No. 31, Hot 100)

It’s hard to overstate how ahead of her time Gentry was with this single, a nuanced portrait of a young woman who becomes a sex worker when her mother was left with no other options to care for her -- when Reba McEntire covered the song in 1991, some radio stations still edited out the song’s redemptive conclusion, just as they had in 1969. “‘Fancy’ is my strongest statement for women’s lib, if you really listen to it,” she told U.K. magazine After Dark in 1974. “I agree wholeheartedly with that movement and all the serious issues that they stand for -- equality, equal pay, day care centers and abortion rights.”

Like her Hot 100-topping 1967 breakout hit “Ode to Billie Joe,” “Fancy” was penned by Gentry alone, another clear-eyed, artfully told story that proved a compelling window into Southern life for listeners. The song’s production is similarly forward-looking, an easy blend of twangy country guitar, smooth pop strings and R&B horns that more than holds up 50 years later. The breakdown in the middle, where Gentry describes how Fancy became the lady she’d always wanted to be -- if not in the way she’d imagined -- is practically gospel, except the punchline is, “And I got me a Georgia mansion/ And an elegant New York townhouse flat/ And I ain’t done bad” instead of “Amen.” An ideal prayer for the then-newly mainstream altar of women’s self-reliance. -- N.W.

8. Tommy James and the Shondells, "Crimson and Clover" (No. 1, Hot 100)

By the late '60s, a number of the era's mainstays were turning toward the sounds of psychedelia with some desperation, looking to score a hit with a counterculture sound they didn't necessarily understand. So it's no small feat that Tommy James and the Shondells -- who started as a good-time party-rock outfit before morphing into bubblegum hitmakers -- not only adapted to but excelled at psych-pop, scoring a No. 1 smash in "Crimson and Clover." With a vertiginous guitar lick that hits your brain like a field of poppies outside Emerald City, backing vocals that sound beamed in from another galaxy and wah-wah pedal galore, "Crimson and Clover" surpasses the band's previous triumphs before it even gets to the chorus. And when that spine-tingling, tremolo-laden final chorus hits, it's like reaching a previously unexplored state of blissful consciousness -- and feeling it oh-oh-oh-ver and oh-oh-oh-ver. -- J.L.

7. Joni MItchell, "Both Sides Now" (Did not chart)

No pop song has ever put things into perspective quite like Joni Mitchell's daydreamy "Both Sides Now," with its timeless look at love and life and how we may never understand either. Mitchell's perfectly poetic lyrics ("Something's lost but something's gained in living every day") seem to raise more questions than answers. But taking the time to ponder life's big mysteries -- as she does so beautifully here, albeit with a more pragmatic and less dramatic delivery than Judy Collins in her top 10 hit version from a year earlier -- might be just the solution she's after. Proving its endurance, the song took on a new life more than 30 years later thanks to a poignant scene in the 2003 rom-com Love Actually, where a 2000 re-recording of the song plays mournfully over Emma Thompson's heart-wrenching discovery that her husband has been unfaithful. Just as the song paints a picture of "fairy tale" love, it also cautions, "If you care, don't let them know" -- and right on cue, Thompson dries her tear-soaked face, straightens out her clothes and fakes a big smile in front of her unaware family. -- K.A.

6. Creedence Clearwater Revival, "Fortunate Son" (No. 14, Hot 100)

The 1960s were rife with anti-war anthems, but it was John Fogerty’s twangy flipping off of wartime class disparity that hit the hardest. At the time, President Richard Nixon’s daughter had just married Dwight Eisenhower’s grandson -- nuptials that, to Fogerty, personified the elitism that shielded affluent families from the draft. “I ain’t no senator’s son,” the CCR frontman spat in response, with a shimmer of pride that resonated with a generation.“Fortunate Son” was added to the National Recording Registry by the Library of Congress in 2013 for being “culturally, historically, or aesthetically significant,” and forever tied Creedence Clearwater Revival’s legacy to the Vietnam War, in a way since commemorated by more period movies than should be humanly possible. But the song itself transcends its history -- amid a nation locked in protest, Fogerty’s snarl forever sends a new shiver down the spine. -- T.C.

5. Isaac Hayes, "Walk on By" (No. 30, Hot 100)

“I didn’t ask you for it, but you gave me,” Isaac Hayes sings in a low voice so bereft, you want to give the man a hug or a drink. He’s speaking about the tears and sadness his ex gave him by breaking his heart, but in a way he’s also describing the experience of “Walk on By,” a 12-minute epic that explodes the radio-ready neatness of Motown singles and sanitized, quality-controlled soul. (Dionne Warwick’s delicate, Grammy-nominated original incarnation of “Walk on By,” written by Burt Bacharach and Hal David, is a lean 2:55.) No one could have thought to ask for this, because soul wasn’t really being made at this scale, with such total creative freedom, before. Impossibly lush and deep, Memphis group the Bar-Kays served as Hayes’ backing band for “Walk on By,” and they’re just as crucial to the song’s success as Hayes’ strained performance. Prefiguring early ‘70s runtime-busters like Marvin Gaye’s “Right On,” Harold Melvin and the Blue Notes’ “I Miss You” and Stevie Wonder’s “Superwoman,” “Walk on By” remains inspiring and unique -- Isaac Hayes gave us that. -- R.S.

4. The Rolling Stones, "Gimme Shelter" (Did not chart)

The haunting opening sounds like Chuck Berry slowed down and awaiting the apocalypse. The lyrics evoke a person at their wits end, watching some sort of societal collapse: “Rape, murder -- it’s just a shout away!” And then there’s Merry Clayton, giving one of the most legendary vocal performances in music history as Jagger carnival barks the impending doom. It’s a great record, pure and simple -- the kind of song that transcends and ascends. At the end of the 1960s, with assassinations, cult leaders and so much else making headlines as the “Flower Power” era wrestled with its ideals, the song was especially potent. But there’s a sad timelessness to feeling like the end is nigh -- for all of the gloom and doom in the music and lyrics, "Gimme Shelter" endures because 50 years later, with ICE raids and mass shootings, it still feels like disaster is just a shout away. -- S.W.

3. Crosby, Stills & Nash, "Suite: Judy Blue Eyes" (No. 21, Hot 100)

Crosby, Stills & Nash were hardly the first rock supergroup, but they might've been the first to arrive with a single of Endgame-like ambition to match their combined largesse. The frivolous "Marrakesh Express" was the debut album's lead single, but the real smash was "Suite: Judy Blue Eyes," a four-part odyssey written by Stephen Stills as an ode to his winding relationship with fellow '60s star Judy Collins; a love song, breakup ballad and reconciliation plea in one. The song repeatedly changes tempo, vibe and subject but never feeling, a wistful delirium in which joy, pain, hope and nostalgia are all interchangeable. Lovingly stitched together like a decades-old quilt and unified by the trio's spectral, game-changing harmonies, "Suite" belongs on a very short list with "Bohemian Rhapsody," "Sicko Mode" and just a handful of other singles from the rock era of songs that combine discrete sections into one lengthy epic, but still remain unquestionably, centrally pop -- both painfully beautiful and thrilling to the marrow. -- A.U.

2. Sly and the Family Stone, "Everyday People" (No. 1, Hot 100)

At the height of the Civil Rights Movement, marginalized communities were begging for peace. And while music couldn’t hold all the answers, it did aid in comforting those who were in search of them. Sly and the Family Stone's “Everyday People,” their first Hot 100-topper served to heal as much as to entertain. The band was one of the first to include members of different races and genders, which made mocking lyrics like “There is a blue one who can't accept the green one/ For living with a fat one, trying to be a skinny one” all the more resonant. And even if racist folks wanted to caulk their ears at anything regarding equality, the brilliance of frontman Sly Stone’s production masked the important message with sturdy piano, frilly guitars and sing-song "na-na na-na boo-boo” cadences, which even the most stubborn couldn’t help but groove to just a little. And back in those days, that little push could end up moving mountains of misery. -- B.G.

1. The Zombies, "Time of the Season" (No. 3, Hot 100)

While most of the band's 1968 album Odessey and Oracle veers toward baroque pop, the Zombies returned to the jazz-inflected rock of previous hits "She's Not There" and "Tell Her No" on album closer "Time of the Season." Colin Blunstone sounds hazy and deliciously haughty while delivering gems like "Who's your daddy? Is he rich like me?" with palpable disinterest, and the music bleeds cool, from that prowling tomcat of a bass line to the feverish organ solos, to the eerie sigh of release that recurs throughout. It's an enduring, idiosyncratic classic that has come to be one of the defining songs of the era -- even if the world didn't catch on so quickly. By the time the song debuted on the Hot 100 in 1969, eventually peaking at No. 3, the band had already broken up, frustrated by the initial indifference to a song and album now rightly regarded as artistic high points of the decade. -- J.L.