It’s the most illustrious prize in music, so every year we still gather around our televisions (and now, on social media) to complain about how the Recording Academy got it wrong. The Grammy winners for Album of the Year do collectively rise above that reputation, even if the voters often ignored the biggest and best new records, the innovators and the boundary pushers, to go their own way. Revisiting the nearly seven-decade history of this award may not be a comprehensive education in the evolution of popular music, but it is an enjoyable whirl through the canon and a revealing peek into what the industry values — especially, as technological changes have eroded its power, the sense of tradition in which it has increasingly found comfort.
66. September of My Years Frank Sinatra (1966)
This concept album about the twilight of life made Frank Sinatra the first repeat winner of the Grammys’ top prize. It’s so languid that you may feel yourself age before it's over.
Standout track: "It Was a Very Good Year"
65. Unplugged Eric Clapton (1993)
Eric Clapton's MTV-powered comeback was a genuine cultural moment. Unfortunately, this collection of yuppie blues wouldn't be the last time that the Recording Academy embraced Starbucks music over more exciting competition.
Standout track: "Running On Faith"
64. Babel Mumford & Sons (2013)
There’s nothing inherently wrong with a stomp-clap crescendo, but these plucky British folk-rock revivalists return to that well on nearly every track, often to signify pushing through doubt. Loud is not an emotion.
Standout track: “Hopeless Wanderer”
63. Genius Loves Company Ray Charles (2005)
Carried by a wave of sympathy mere months after his death, Ray Charles received the top Grammy honors that eluded him at the prime of his career for this duets collection. His updates of standards such as “Here We Go Again,” “Fever” and “Over the Rainbow” are likable enough, sometimes even lovely — and had absolutely no business beating the modern classics (The College Dropout! American Idiot! Confessions! The Diary of Alicia Keys!) nominated against Genius Love Company.
Standout track: “Crazy Love (Live)”
62. Unforgettable...With Love Natalie Cole (1992)
After lipsyncers Milli Vanilli had their Best New Artist award revoked, the Grammys retrenched into a shame and traditionalism that took nearly two decades to fully shake off. It was already in clear effect by the following ceremony, when Natalie Cole took the top prize. Though Unforgettable...With Love turned out to be a surprise phenomenon — propelled by the titular duet with her late father, the legendary Nat King Cole — its win feels 30 years out of date. For vast stretches, the album is also the classiest, most beautiful sleeping aid you could ask for.
Standout track: "Avalon"
61. The Concert for Bangladesh George Harrison & Friends (1973)
George Harrison's east-meets-west benefit show, featuring Ravi Shankar, Billy Preston, Ringo Starr and Bob Dylan, raised millions for refugees of the Bangladesh Liberation War and pioneered the all-star charity concert. Five decades removed, this live recording feels more well-intentioned than essential.
Standout track: "Bangla Dhun"
59. The Music from Peter Gunn Henry Mancini and His Orchestra (1959)
Though the first ever Grammy winner for Album of the Year — a jazz soundtrack more popular than the private eye television series it originated from — hardly carries a cultural footprint anymore, it’s fine accompaniment for a cocktail party with Don Draper.
Standout track: "Dreamsville"
58. A Man and His Music Frank Sinatra (1967)
An exhaustive (and exhausting) tour through Frank Sinatra's decades of hitmaking, narrated by Ol' Blues Eyes himself like a Vegas lounge show. It was his third and final Album of the Year winner in just eight years, though he’d be up for the prize twice more; his eight total nominations have yet to be surpassed by any act.
Standout track: "All or Nothing At All"
58. River: The Joni Letters Herbie Hancock (2008)
Legendary jazz pianist Herbie Hancock’s reinventions of Joni Mitchell tunes can be inspired at times, but awarding them — over instant classics such as Amy Winehouse’s Back to Black and Kanye West’s Graduation! — does not make up for the Grammys failing to properly recognize the Lady of the Canyon at the height of her career.
Standout track: “The Tea Leaf Prophecy (Lay Down Your Arms)”
57. The Barbra Streisand Album Barbra Streisand (1964)
The supreme diva was already firmly in her element at just 20; "Happy Days Are Here Again" is simply a stunner. While this debut album marked the first step from Broadway to entertainment industry domination, Barbra Streisand would go on to record more iconic music.
Standout track: "Happy Days Are Here Again"
56. Midnights Taylor Swift (2024)
Is Taylor Swift the greatest artist of all time? Perhaps it’s a debate that needs to be had, but crowning her now feels premature. So does a fourth Album of the Year prize — more than any other musical act ever, more than all Black women combined — especially for something as paint-by-Swiftian-numbers as Midnights. This is not a standout in her frequently remarkable catalog; sultry slow burners give way too often to juvenile cutesiness and a victimhood mentality that Swift seemed to have finally outgrown. (Only on “Karma,” winking so hard that she threatens to strain an eye muscle, does it work.) But the Record Academy was probably celebrating less the music than its record-setting sales, accompanied by a global stadium tour and blockbuster concert doc that cemented Swift in another league of pop superstardom. The best songs (“Would’ve, Could’ve, Should’ve,” “Bigger Than the Whole Sky”) are actually from one of several bonus editions she released to juice her chart domination.
Standout track: “Sweet Nothing”
55. Can't Slow Down Lionel Richie (1985)
The poster child for the Grammys getting it exactly wrong. (It beat Purple Rain, Born in the U.S.A., She's So Unusual and Private Dancer.) But Can't Slow Down is better than its reputation — as long as Lionel Richie is sticking to his titular promise and steering clear of treacly ballads.
Standout track: "All Night Long (All Night)"
54. Back on the Block Quincy Jones (1991)
Super producer Quincy Jones brought together all his famous friends (well, not Michael Jackson) for a spin through the Black popular music tradition that ties jazz and R&B to then-relatively young rap and the emergent new jack swing style. Its cross-generational innovation aims for timelessness but now sounds incredibly dated, albeit with a few minor triumphs, including a groovy rendition of "Birdland," along the way.
Standout track: "I'll Be Good to You"
53. The Button-Down Mind of Bob Newhart Bob Newhart (1961)
It's rather odd, six decades later, to realize that comedy albums once contended for the Grammys' top prize. Bob Newhart's standup — short sketches featuring one side of an absurdist conversation — has held up fairly well.
Standout track: "Driving Instructor"
52. MTV Unplugged Tony Bennett (1995)
In a lineup that may mark the lazy low point of this category — including two follow-up releases from recent winners and a live Three Tenors concert — the jazz legend who suddenly found himself an MTV favorite in his late sixties probably was the hippest choice the Recording Academy could have made. Not that Tony Bennett's televised special of standards is exactly cool, but it achieves groovy liftoff on occasion, launched by his crackling rich voice.
Standout track: "The Girl I Love"
51. O Brother, Where Art Thou? – Soundtrack Various Artists (2002)
Perhaps the most unusual winner in the canon — yes, even more than the comedy album by the JFK impressionist — is this collection of Depression-era country, blues, gospel and Southern folk music, the soundtrack to a moderately successful Coen Brothers comedy that somehow became an octuple-platinum event on the way to beating Bob Dylan and Outkast. It's an amazing story for a solid album. But giving U2 their comeback award for the superior All That You Can't Leave Behind instead of four years later is an alternate history that might have solved some of the Recording Academy's aughties identity crisis.
Standout track: "Hard Time Killing Floor Blues"
50. The Bodyguard: Original Soundtrack Album Whitney Houston (1994)
What begins a veritable Whitney Houston greatest hits collection ("I Will Always Love You"! "I Have Nothing"! "I'm Every Woman"!) wastes its back half with a hodgepodge of soundtrack ephemera from the film sensation, of which only Lisa Stansfield's light dance bop "Someday (I'm Coming Back)" makes much of an impression.
Standout track: "I Have Nothing"
49. Falling Into You Céline Dion (1997)
A triumph of popularity over artistry and maybe taste. Yet there's something oddly enjoyable about the kitchen-sink maximalism of Falling Into You, which never lacks for passion. It's so much more than the adult contemporary cheese for which Céline Dion is derided.
Standout track: "It's All Coming Back to Me Now"
48. Two Against Nature Steely Dan (2001)
When Alphonse Karr observed that the more things change, the more they stay the same, perhaps he was thinking of Steely Dan's much-hyped reunion album, which sounds straight out of their heyday two decades prior. That also would have been a better time to honor the jazz-rock duo, whose amiable grooves on Two Against Nature lacked the urgency of fellow nominees such as Radiohead, Eminem and Beck.
Standout track: "Two Against Nature"
47. We Are Jon Batiste (2022)
The first album by a Black artist to win Album of the Year in more than a decade — and nearly two if you're looking for original songs — underscores the Recording Academy’s ongoing struggle to reckon with how hip-hop has reconfigured the landscape of popular culture. On We Are, virtuosic multi-instrumentalist Jon Batiste dabbles in soul and the blues, gospel and jazz. He sounds at times like Al Green and James Brown and Prince. Though the record made no noise on the charts, it falls neatly into the narrow band of roots-conscious nostalgia through which voters seem capable of fully embracing the African-American musical tradition anymore. A handful of feints toward something more contemporary, such as the tongue-twisting delivery of “Whatchutalkinbout,” are a further reminder that we’re still waiting for the coronation of a rapper to herald that the future has finally, truly arrived at the Grammys.
Standout track: “Cry”
46. Blood, Sweat & Tears Blood, Sweat & Tears (1970)
Grab a doobie, flower children, and enjoy the Recording Academy's belated embrace of the (sort of) counterculture. There's a certain stoned brilliance to Blood, Sweat & Tears' artistry — opening and closing the album with variations on an Erik Satie composition — and also the inevitable meandering diversions of an altered state.
Standout track: "More and More"
45. Toto IV Toto (1983)
Sure, the corporate rock that came to dominate the music industry at the dawn of the MTV era could be schlocky. But those ridiculously catchy hooks filled stadiums for a reason.
Standout track: "It's a Feeling"
44. The First Family Vaughn Meader (1963)
A fascinating relic of its time. The joke construction quickly grows familiar — a seemingly serious situation is undercut by Vaughn Meader's honking, boorish JFK, who has no interest in politics — but many of the punchlines still land.
Standout track: "Economy Lunch"
43. Come Dance With Me! Frank Sinatra (1960)
Blaring with horns and all the pep its titular exclamation point suggests, this big band collection is a lively swing around the midcentury dance floor. The listener's energy may be sagging by the time a ballad arrives to offer a rest break.
Standout track: "Something's Gotta Give"
42. How to Dismantle an Atomic Bomb U2 (2006)
Not nearly as politically charged as its title would suggest, U2 can still make you dance (“Vertigo”) and weep (“Sometimes You Can’t Make It On Your Own”) on their second Album of the Year winner. Yet How to Dismantle an Atomic Bomb does feel like the precipice of their slide into toothless adult rock.
Standout track: “City of Blinding Lights”
41. 25 Adele (2017)
Adele goes bigger, but not necessarily better, on her second consecutive Album of the Year winner. No doubt, the pressure to follow up the earth-shattering success of 21 must have been immense. In trying to give audiences another dose of what they thought they wanted while still exploring new artistic territory, however, 25 loses some of the spark of its predecessor. It’s more capital-P pop, more slickly produced, more of a pitch straight down the middle — and less creatively and sonically cohesive, less charmingly Adele. A few new breathtaking heartbreak ballads (she did give us another classic with “Hello”) sit alongside some sweet tributes to her young son, though the best moments are dark and dazzling downers grappling with how her life has changed since fame (“Million Years Ago”). When Adele sobbed on stage about how the trophy should have gone instead to Beyoncé’s Lemonade, she wasn’t wrong.
Standout track: “River Lea”
40. Still Crazy After All These Years Paul Simon (1976)
Paul Simon softens, musically and emotionally, on this post-divorce collection of gentle midtempo ballads and sentimental storytelling.
Standout track: "Still Crazy After All These Years"
39. Christopher Cross Christopher Cross (1981)
The soft rock king took Grammy domination to new heights, becoming the first artist to sweep the general field at a ceremony and earning an eternal side-eye from discerning listeners in the process. His self-titled debut is perfectly pleasant and totally slight. But "Sailing," man, what a song!
Standout track: "Sailing"
38. Harry’s House Harry Styles (2023)
This boy-bander-made-good isn’t quite George Michael — but who is? Blaring funk horns, shimmery disco grooves and sunny California rock make Harry’s House a nice place to stop for a visit.
Standout track: “Music For a Sushi Restaurant”
37. Getz/Gilberto Stan Getz and João Gilberto (1965)
A breakthrough for world music, the soft and sultry bossa nova style that Getz and Gilberto introduced to American audiences is now so familiar as to border on elevator music, though it's never less than lovely.
Standout track: "O Grande Amor"
36. 24K Magic Bruno Mars (2018)
You can never go wrong with the Recording Academy making new music that sounds like old music. The new jack swing bangers and smooth R&B ballads on his turn-of-the-nineties third album clinched Bruno Mars’ ascent to Grammy darling.
Standout track: “Finesse”
35. Raising Sand Robert Plant and Alison Krauss (2009)
Yes, it’s the third covers album to win in five years, a tiresome reflection of the Recording Academy’s blinkered tastes during the aughts. Yet Robert Plant and Alison Krauss meld into something surprising and raw on the occasionally funky, occasionally haunting Raising Sand.
Standout track: “Gone Gone Gone (Done Moved On)”
34. 52nd Street Billy Joel (1980)
It’s a classic Recording Academy move to hand someone a compensatory Grammy for an earlier work they didn’t fully embrace in its moment — in this case, The Stranger, which launched Billy Joel into his imperial period just a few years earlier but was recognized only for single “Just the Way You Are.” Though 52nd Street isn’t packed with nearly as many future Joel standards, the Piano Man was still riding high with his first #1 album, in fine form on the self-lacerating “Big Shot” and the jazz fusion ode “Zanzibar.” Amid the burgeoning disco backlash, his old-school theatrical showmanship must have been a comfort to voters.
Standout track: “Zanzibar”
33. Fearless Taylor Swift (2010)
If Taylor Swift was destined to win this prize more times than anyone else in Grammy history, then perhaps her sophomore effort — where fairytale imagery collides with sparkling ballads that can feel wise beyond her 19 years — was a touch too soon to begin rewarding her.
Standout track: “Fifteen”
32. Morning Phase Beck (2015)
Beyoncé’s self-titled visual album, which changed the game with its surprise digital drop and accompanying music video for every track, remains a staggering accompl—sorry, I’m still not over that shocking snub a decade later. When everyone expected the Recording Academy to zig, they instead zagged to Beck’s shaggy folk psychedelia, an unassuming target for outsized backlash. Morning Phase, delicate and elegant, is actually a pleasant ride. But please, it’s no Beyoncé.
Standout track: “Waking Light”
31. Double Fantasy John Lennon and Yoko Ono (1982)
A musical dialogue of marital (mostly) bliss that surely felt more resonant in the wake of John Lennon's murder mere weeks after the album's release and that probably would not have won the Grammy if not for that tragedy.
Standout track: "(Just Like) Starting Over"
30. Supernatural Santana (2000)
The most awarded album in Grammys history — a reflection of Santana's unexpected, Rob Thomas-aided domination of the zeitgeist at the turn of the millennium, but also how the cross-genre, intergenerational collaborations with everyone from Everlast and Dave Matthews to Lauryn Hill and Eric Clapton played right to the Recording Academy's sweet spot. Supernatural is full of thrills both conventional ("[De La] Yaleo") and forward-looking ("Maria Maria"), though inspiration sags by the end of its hefty runtime.
Standout track: "Migra"
29. Judy at Carnegie Hall Judy Garland (1962)
A monumental double album capturing Judy Garland's historic Carnegie Hall concert, its two hours brimming with the dizzying vocals and wrenching emotion of one of pop music's great musical interpreters. As an increasingly rambunctious audience banters with Garland between songs, calling for encore after encore, it only reinforces how electric she must have been to witness live that night.
Standout track: "Somewhere Over the Rainbow"
28. Nick of Time Bonnie Raitt (1990)
Bonnie Raitt's late career breakthrough with Nick of Time, her tenth studio album, is one of the great Grammy triumphs. The album isn't quite as sensational as the story, though it comes close with rootsy rock ballads like the title track. Not so much the more dated production flourishes of the era, including the oddly reggaefied "Have a Heart."
Standout track: "Nobody's Girl"
27. No Jacket Required Phil Collins (1986)
With Phil Collins' enthusiastic howls layered on top of pounding gated drums and blaring horns, pop music has perhaps never been louder. Get ready to pump your fist!
Standout track: "Don't Lose My Number"
26. Time Out of Mind Bob Dylan (1997)
Decades removed from his troubadour peak — which was never rewarded by the Recording Academy! — Bob Dylan enjoyed resurgent relevance with this moving contemplation of lost love and mortality. In a Grammy epoch dominated by tradition and questionable Album of the Year winners, Time Out of Mind's coronation is the rare makeup award that holds up.
Standout track: "Standing In the Doorway"
25. Speakerboxxx/The Love Below Outkast (2004)
Despite becoming our dominant musical language over the past three decades, hip-hop has been shamefully unappreciated at the Grammys. Only the second, and to date final, Album of the Year winner from the genre is Outkast’s fractured double disc — Big Boi’s funky party starters on Speakerboxxx, followed by André 3000’s jazzy bedroom symphony on The Love Below — which honestly probably won because it also gave us one of the greatest pop hits of all time. (Shake it like a Polaroid picture!) In retrospect, this is not the duo’s strongest collection; it’s an ambitious but bloated portrait of a genius collaboration coming apart at the seams. Yet there’s enough material here to more than fill one stellar album. Crank up “GhettoMusick” or “Roses,” “Bowtie” or “Last Call” or “Happy Valentine’s Day,” and revel.
Standout track: “Hey Ya!”
24. Fulfillingness’ First Finale Stevie Wonder (1975)
Fresh off a car crash that briefly left him in a coma, Stevie Wonder largely leaves behind social commentary (with the exception of the great #1 hit “You Have’'t Done Nothin’”) and steers back toward personal reflection. He is consumed by loss, often of a lover but occasionally of a spiritual nature — an angst that can be divine (“Heaven Is 10 Zillion Years Away”) or too self-serious (“They Won’t Go When I Go,” the album’s worst song). That this is the least of Wonder's Grammy-winning trio of albums only underlines what a creative streak he was on.
Standout track: “Heaven Is 10 Zillion Years Away”
23. By the Time I Get to Phoenix Glen Campbell (1969)
The Grammys’ first country honoree for Album of the Year is a graceful set of plain and plaintive ballads. Its subtle emotional power sneaks up on you.
Standout track: “Love Is a Lonesome River”
22. Golden Hour Kacey Musgraves (2019)
With her head in the stars and her heart on her sleeve, spacey Kacey Musgraves’ exquisite sunset jams about love and gratitude proved that the Recording Academy could still savor small joys, even as it expanded this category into a supersized field of contenders.
Standout track: “Slow Burn”
21. The Suburbs Arcade Fire (2011)
This indie rock concept album about growing up in and fleeing suburbia, a sort of origin story for Arcade Fire’s creative mastermind Win Butler, is a unique champion in the history of this category — perhaps the hippest that the Grammys has ever seemed in the moment.
Standout track: “Sprawl II (Mountains Beyond Mountains)”
20. 1989 Taylor Swift (2016)
This is the sort of pop record — a culture-monopolizing blockbuster turbocharged by glittering earworms — that the Recording Academy hadn’t embraced since George Michael’s Faith in, well, 1989. Nearly every track could be a single and most of them were.
Standout track: “Style”
19. ‘Saturday Night Fever’ Soundtrack Various Artists (1979)
The half dozen Bee Gees songs most closely associated with this iconic soundtrack are all-timers. Its pleasures go even deeper, however, through several more disco classics (“If I Can’t Have You,” “Disco Inferno,” “Boogie Shoes”) and some unforgettable instrumentals (“A Fifth of Beethoven”).
Standout track: “More Than a Woman”
18. Random Access Memories Daft Punk (2014)
Despite being headlined by the party anthem of summer 2013, the first electronic music Album of the Year winner is hardly for the clubs. Random Access Memories is quaaludes disco, moody and meditative and melancholy, like free jazz as interpreted by a pair of French robots. That back-to-the-future approach is probably why the perpetually nostalgic Recording Academy finally felt comfortable enough to take a leap into the digital age.
Standout track: “Get Lucky”
17. Folklore Taylor Swift (2021)
Forged in the depths of the coronavirus pandemic, Folklore is Taylor Swift stripped down to her essence. Sparse arrangements foreground expansive storytelling, often beyond Swift’s own perspective, channeling the dour isolation of a global catastrophe into some of the finest work of her career. Even if the album doesn’t pack quite the same punch that it did on long walks through lonely streets in the summer of 2020 — it ends in a somewhat indistinguishable muddle of dirges — this feels like Swift becoming the artist that we were always waiting for.
Standout track: “Invisible String”
16. Come Away With Me Norah Jones (2003)
So much more vital than everything it came to represent, Norah Jones’ jazzy debut is warm and observant and sexy (oh, so sexy!). An impressively mature artistic statement for an early twentysomething, Come Away With Me feels like a Tapestry for a new generation. It’s a worthy Album of the Year winner, despite some tremendous competition and an unfair legacy as waiting room music.
Standout track: “Nightingale”
15. When We All Asleep, Where Do We Go? Billie Eilish (2020)
A spectacularly confident debut for a 17-year-old. With production assistance from her brother, Billie Eilish slinks through mind-bending, hip-hop-inflected alternative soundscapes with winking wit and raw eartnessness. It was a good bet on the future by the Recording Academy. Since sweeping the general field — the first artist to do so since Christopher Cross — Eilish’s subsequent releases have only gotten more impressive.
Standout track: “Bad Guy”
14. Taking the Long Way The Chicks (2007)
A defiant middle finger to the country music establishment that dropped the Chicks after Natalie Maines’ infamous anti-war stand in 2003, Taking the Long Way finds release in that repudiation. Free to venture away from their roots, the band plays around with pop, rock and blues on their vulnerable and gorgeous ruminations about motherhood, marriage and, of course, the fallout from the Dubya diss heard ‘round the world.
Standout track: “Not Ready to Make Nice”
13. Bridge Over Troubled Water Simon & Garfunkel (1971)
Did Paul Simon invent the breakup album? His final studio collaboration with Art Garfunkel is at its most poignant tracing the dissipation of their creative partnership. Written solo while Garfunkel was pursuing movie stardom, songs like “The Boxer” and the titular “Bridge Over Troubled Water” are a showcase of Simon’s all-time songwriting genius.
Standout track: “The Only Living Boy In New York”
12. Thriller Michael Jackson (1984)
Birthed of Michael Jackson's ambition to record an album on which “every song was a killer,” Thriller almost achieves that pop perfection. (Sorry to lead single “The Girl Is Mine,” which is an absolute drag, despite the presence of Paul McCartney.) Four decades later, its cultural force has not dimmed — Thriller’s sales and Grammy sweep remain in the record books, while the title track resurges each Halloween — and the Quincy Jones production still sparkles. But it’s tough to love now, in light of revelations about Jackson’s alleged abuses.
Standout track: “P.Y.T. (Pretty Young Thing)”
11. Faith George Michael (1989)
Sex! It's on George Michael's mind a lot on his slinky solo debut — having it, not having it with the wrong person, wanting it to mean something deeper. Even in a more prudish era of AIDS panic and Ronald Reagan, when Michael had to film a monogamy PSA to air on MTV before the music video for his lead single “I Want Your Sex,” audiences lapped it up to the tune of four #1 hits and two more top tens. They are all absolute bangers, grandiose monuments to the creative ambition of pop music at its finest. (The acoustic guitar hook on “Faith”! The gorgeous sweep of “One More Try”!) And though Faith doesn’t add up to much in the way of a larger statement, it hardly takes a wrong step either, even on the slightly mean-spirited “Look at Your Hands.”
Standout track: “Father Figure”
10. Innervisions Stevie Wonder (1974)
Stevie Wonder trades R&B hit-making for a sermon on America’s soul and its path to salvation on the first of his historic run of Grammy winners. Praise above all to his astonishing voice, in glorious peak form — supple, enveloping, one of the greatest ever in popular music.
Standout track: “Living For the City”
9. 21 Adele (2012)
Turning personal heartbreak into cultural zeitgeist, Adele’s sophomore stunner briefly convinced us all that the album wasn’t dead. It’s hard to pinpoint exactly what made it an unexpected diamond-selling phenomenon. Defiantly furious as often as it’s achingly wounded, 21 flits between rollicking kiss-offs and sparse piano ballads, retro grooves and stratospheric belts, acknowledging that the end of a relationship can be messy and getting over it is a process. Perhaps it simply boils down to that voice, an unforgettable wail so deeply felt that it makes every song sound like it’s been lifted straight from your own soul.
Standout track: “Someone Like You”
8. Jagged Little Pill Alanis Morissette (1996)
Out of the wilderness of failed Canadian teen pop stardom, Alanis Morissette’s not-quite-debut album emerged like a thunderbolt of emotional expungement. The resonance of its lacerating lyricism and self-help aphorisms, grungy guitars and harmonica solos, not to mention a shaky grasp of certain literary devices and a furious grudge against Full House’s Uncle Joey, was strong enough to drive diamond sales and help shake the Recording Academy out of its nostalgic stupor. Three decades later, it still rips.
Standout track: “Ironic”
7. Graceland Paul Simon (1987)
An album that could have been sunk by controversy — Paul Simon faced scorn for traveling to South Africa to record in spite of the cultural boycott against its apartheid government, even winding up an assassination target for one extremist group — instead became a multimillion seller and a Grammy winner, reviving Simon’s career and redefining his legacy. Credit the genuine innovation of his collaborations with Black musicians such as Ray Phiri and Ladysmith Black Mambazo, whose polyrhythmic styles brought an edge to Simon’s soft rock that still feels startlingly vital, and the openhearted spirit of Graceland, an understated appeal for interracial solidarity that arguably helped further the anti-apartheid cause as much as any protest anthem by his peers.
Standout track: “You Can Call Me Al”
6. Tapestry Carole King (1972)
Unencumbered, often accompanied by just a piano, Carole King’s voice is a cozy embrace. On Tapestry, she guides listeners through a diaristic meditation on lovers and friends, loneliness and self-confidence, paving the way for generations of female singer-songwriters to come.
Standout track: “So Far Away”
5. The Joshua Tree U2 (1988)
Love and war, faith and identity, the American Dream and Cold War interventionism — The Joshua Tree is bursting with big themes and bigger emotions, not to mention three of the greatest power ballads in rock history. It’s the album that elevated U2 from alternative favorite to the most famous band in the world and it remains a wonder, at once searching and politically pointed. Bono, not yet having found what he’s looking for, is ferociously raw, his famous sentimentality still piquant and far from its later goopiness.
Standout track: “With or Without You”
4. The Miseducation of Lauryn Hill Lauryn Hill (1999)
A Grammy triumph that feels even more remarkable in retrospect. Consider the banger lineup of nominees (Madonna! Shania Twain! Sheryl Crow! Garbage!), still the only time that every Album of the Year contender was by a woman or a female-fronted act. Lauryn Hill, just 23 years old, emerged victorious with the first hip-hop album to claim the top prize, a feat that has been replicated once in the quarter-century since. She is also, shamefully, the last Black woman to date to win. It’s a stark display of the Recording Academy’s longstanding failure to recognize the full scope of popular music, but also a testament to the power of The Miseducation of Lauryn Hill that it momentarily broke through the biases and traditionalism. Hill may never have followed up on the promise of her kaleidoscopic debut — which seamlessly pulls together virtuosic rapping and soul-bearing R&B belting, acoustic guitar and playful skits set in a classroom — but it remains an unforgettable statement.
Standout track: “Ex-Factor”
3. Rumours Fleetwood Mac (1978)
Emotional turmoil. Romantic chaos. Cocaine-fueled genius. Blockbuster sales. The legend of Rumours may eclipse the album itself at this point, especially with five classic singles still fueling its legacy. But there’s a simple poetry to the conversation that plays out from song to song between bitter Lindsey Buckingham ("Go Your Own Way" is a propulsive high point) and disenchanted Stevie Nicks (the ethereal goddess of "Dreams") and hopeful Christine McVie (so achingly beautiful on "Songbird," the record’s beating heart).
Standout track: “You Make Loving Fun”
2. Songs in the Key of Life Stevie Wonder (1977)
An astounding artistic apex for Stevie Wonder — one to which any pop album can only aspire. There is no high concept here, no gimmicks or experimental posturing to hide its shortcomings. It’s just a double album — so hefty it needed a bonus EP on the original wax — stuffed with classics about love and God and racial harmony and new fatherhood, crisp melodies that would one day become essential samples effortlessly exploding into funky jam sessions, and, somehow, no skips. To imagine that he had all of that excellence inside of him at once is a wonder indeed.
Standout track: “Summer Soft”
1. Sgt. Pepper’s Lonely Hearts Club Band The Beatles (1968)
The masterpiece that ushered in a new era of pop music — and Grammys history. On their third nomination, the Beatles finally won Album of the Year, the first rock act to do so. That Sgt. Pepper’s was so revolutionary, such a statement of popular music as a legitimate art form and youth culture as worthy of serious consideration, that it forced even the stodgy Recording Academy to take notice is now taken for granted. Yet an umpteenth spin through the symphonic acid trip of “Lucy In the Sky With Diamonds” or the quotidian cacophony of “A Day In the Life” can still inspire marvel at its boundary-breaking brilliance.
Standout track: “A Day In the Life”
