Listen to the 64 Grammy winners for album of the year, and they’ll tell the story of the last six decades of popular music. Except, well, not really, at all. Zoom out on all 64 and squint a little and you might be able to see a general progression from jazz and vocal standards to rock to pop and hip-hop, but the timeline traced by the album of the year winners is really more of a Jeremy Bearimy: constantly curving, skipping around and looping back unpredictably.
That’s part of the fun of the Grammys canon, though: The tale it tells isn’t always the most coherent, but it’s rich with moment-in-time pretzel logic that makes sense when viewed in totality — not to mention fascinating quirks forgotten in most enduring pop narratives of the past. And every so often, the Recording Academy gets it totally right, rewarding an album so undeniably essential that all voting roads lead back to it as the one and only answer.
Here are those 64 albums — hits, misses, and all negotiations in between — and how they stack up against one another, viewed from the year 2021.
64. Mumford & Sons, Babel (2013)
Despite the cacophonous implications of the title, there’s only one musical language being endlessly repeated here: the empty bombast of stadium folk-rock geared for mass (like, 600k first week mass) consumption, with bleated lyrics like “I miss my sanguine eyes” a laughable substitute for genuine sentiment. By the middle of the second side, the primary stomping you’ll hear is the sound of you kicking in your computer speakers.
Should it Have Won? Inevitable that it did, but any of the other four nominees would have been preferable — particularly Frank Ocean’s epochal Channel Orange or fun.’s theater-kid-rock epic Some Nights.
Not Even Nominated: Fiona Apple’s The Idler Wheel…, Miguel’s Kaleidoscope Dream, Drake’s Take Care
63. Vaughn Meader, The First Family (1963)
“Boy, is Vaughn Meader fucked,” was Lenny Bruce’s famous comedic opening to his first set following the 1963 assassination of president John F. Kennedy. Indeed, roughly the 13,000th biggest consequence of that historic calamity was the instant dissolution of Meader’s comedic career, as his runaway recording success (The First Family reportedly sold a million copies a week at its peak) was entirely based on his impersonation of No. 35, which became so instantly dated that December the LP was immediately pulled from shelves. The set wouldn’t have aged that well anyway, as its jokes are almost all one-note pastiches predicated upon the Kennedys’ level of cultural exposure being pervasive and overwhelming — though the bit with world leaders at a summit placing a deli order for lunch has its charms.
Should It Have Won? Certainly not over Ray Charles’ iconic Modern Sounds in Country and Western Music, and Tony Bennett’s I Left My Heart in San Francisco or Stan Getz & Charlie Byrd’s Jazz Samba would also have been far worthier.
Not Even Nominated: Elvis Presley’s Blue Hawaii, Peter, Paul & Mary’s Peter, Paul & Mary, Bill Evans’ Sunday at the Village Vanguard
62. Ray Charles, Genius Loves Company (2005)
An understandable selection, given both the Recording Academy’s predilection for star-studded collab albums and the outpouring of affection for Charles following his 2004 death — not to mention an overdue apology for the legendary soul and rock innovator never winning in his own lifetime. But beyond the frisky, Norah Jones-assisted redo of Charles’ “Here We Go Again” that opens the set, most of these renditions run the gamut from inessential to flimsy, with Willie Nelson’s strangely uncommitted appearance on “It Was a Very Good Year” coming off particularly ill-advised.
Should It Have Won? Hard to hold it against the Academy given the circumstances — just a shame that it happened the same year a trio of four-quadrant classics were also nominated: Kanye West’s College Dropout, Green Day’s American Idiot and Usher’s Confessions.
Not Even Nominated: The Killers’ Hot Fuss, Jay-Z’s The Black Album, Loretta Lynn’s Van Lear Rose
61. Natalie Cole, Unforgettable… With Love (1992)
The Grammys followed a year of historic, game-changing LP releases by rewarding a predictable collection of pop standards capped by one inspired novelty duet, setting the tone for the award for the rest of its tradition-overwhelmed ’90s. Hard to imagine anyone really needs 73 minutes of Natalie Cole covers of her late father Nat King Cole as anything but the backgroundiest of background music — though the duo’s intermingling on the title track made for a deserved crossover hit, a combination of studio wizardry and unlikely generation-and-realm-crossing magic.
Should It Have Won? Nah. If the Academy didn’t want to give it to Bonnie Raitt a second time in three years for her excellent Luck of the Draw, then R.E.M.’s Out of Time — the alt-rock paragons’ greatest moment of mainstream exposure, led by the peerless “Losing My Religion” — would’ve been a fine choice.
Not Even Nominated: Nirvana’s Nevermind, Red Hot Chili Peppers’ Blood Sugar Sex Magik, A Tribe Called Quest’s The Low End Theory — just to name three albums released on the same day (Sept. 24) in 1991.
60. Eric Clapton, MTV Unplugged (1993)
To be fair to Eric Clapton, he proves a surprisingly good hang on his MTV Unplugged set, which rode both the burgeoning momentum of music television’s new marquee prestige live program and his own “Tears in Heaven”-boosted comeback from earlier in the year to Diamond-certified sales. But over the course of an hour of dusty, low-key blues-rock sauntering, the elder statesman can’t help sag from winning to boring, and inverting one of the most searingly electric radio perennials in classic rock history into a shuffling acoustic lament — scoring a hit with it, no less — remains unspeakably perverse.
Should It Have Won?: U2’s Achtung Baby and Annie Lennox’s Diva were two second-act opening scenes much more inspired than Clapton’s MTV-mandated reinvention.
Not Even Nominated: Michael Jackson’s Dangerous, Mary J. Blige’s What’s the 411?, Beastie Boys’ Check Your Head
59. Frank Sinatra, A Man and His Music (1967)
A musical journey through re-recordings of classics from Sinatra’s first 25 years, narrated by the Chairman himself, and released at a time when he figured youth culture was finally about through with him. The new versions are strong and the narration is occasionally revealing — as when Sinatra alludes to feeling the Beatles breathing down his neck, or refuses to talk about the pre-From Here to Eternity career downturn that nearly had him licked 15 years earlier — but the AOTY would’ve made more sense as a Lifetime Achievement award had he not just won the trophy for the second time a year before.
Should It Have Won? Speaking of the Fab Four — they were long overdue for their first win by now, and their Revolver probably would’ve been a pretty good place to start.
Not Even Nominated: The Beach Boys’ Pet Sounds, The Supremes’ The Supremes A’ Go-Go, The Byrds’ Turn! Turn! Turn!
58. U2, How to Dismantle an Atomic Bomb (2006)
More fun and less annoying a decade-plus later, removed from a million insufferable magazine profiles and Apple promos, as well as the stupefyingly inescapable sound of Bono incorrectly counting to four in Spanish. “City of Blinding Lights” and “Original of the Species” are modest highs the band has yet to return to this century, though the fact that their fearless leader obtusely referred to the set as “our first rock album” showed how their rhetoric was already starting to well outpace their inspiration.
Should It Have Won? Patrick Stump of Fall Out Boy certainly didn’t think so, claiming he stormed out of the ceremony after Kanye West’s Late Registration fell to U2. Kanye would undoubtedly concur, and in this case so would we.
Not Even Nominated: Gorillaz’ Demon Days, M.I.A.’s Arular, Beck’s Guero
57. Paul Simon, Still Crazy After All These Years (1976)
Paul Simon’s post-Garfunkel brand of mid-life-crisis rock hit its commercial apex with Still Crazy, winning his first of two solo AOTYs and spawning his first and only solo No. 1 hit with the slinking commitmentphobia anthem “50 Ways to Leave Your Lover.” The appeal to a generation of aging boomers isn’t exactly hard to pinpoint, but it was a lot more fun on 1973’s more tonally and musically varied There Goes Rhymin’ Simon — faux jams like “Have a Good Time” are jaded missives from a singer-songwriter who still feels like he’s holding back on how truly cynical he’s already gotten.
Should It Have Won? Justice for Captain Fantastic and the Dirt Brown Cowboy, the strongest front-to-back set from the peak run of ’70s superstar Elton John — a three-time nominee and zero-time winner.
Not Even Nominated: Led Zeppelin’s Physical Graffiti, Bruce Springsteen’s Born to Run, Fleetwood Mac’s Fleetwood Mac
56. Bob Newhart, The Buttoned-Down Mind of Bob Newhart (1961)
The first-ever comedy album to win the Grammys’ marquee award was this unlikely blockbuster, which exposed audiences reared on Henny Youngman to a new brand of comedy that still feels at least vaguely modern over half a century later. The repeat setup of the one-sided telephone conversation gets a little second-verse-same-as-the-first over the course of the LP, but lay most of these tracks over the video of a Seinfeld standup intro or a Late Show With Stephen Colbert monologue and it’d feel about right.
Should It Have Won? Possibly, since the ’61 crop wasn’t exactly the strongest competition — though if you think Sinatra deserved a fourth AOTY, his ballad set Nice ‘n’ Easy would’ve been a credible enough pick.
Not Even Nominated: The Sound of Music Original Cast Recording, Elvis Presley’s Elvis Is Back!, Miles Davis’ Sketches of Spain
55. Tony Bennett, MTV Unplugged (1995)
The slightly more fun of the two ’90s Unplugged winners, thanks to Bennett’s unsurprising superiority — and boundless energy, even at age 67 — as an entertainer. Undoubtedly a healthy portion of the set’s Platinum sales were due to holiday and birthday gifts for relatives who only need one album a year, but there’s legitimate joys to be had here: from Bennett’s solo scat breaks on “The Girl I Love” to k.d. Lang’s surprising-but-welcome appearance on “Moonglow” to the inversion of Sinatra’s jaunty “Fly Me to the Moon” as a soulful, jazzy torch song.
Should It Have Won? Uhhh maybe? The Grammys’ mid-’90s personality crisis resulted in a lackluster ’95 class that ignored one of the greatest years for albums in alt-rock and hip-hop history in favor of Bennett, The Three Tenors, Eric Clapton (again), Bonnie Raitt (again again) and Seal. Take your pick from that bunch, but we won’t begrudge Bennett belatedly getting on the board here.
Not Even Nominated: Nas’ Illmatic, Snoop Doggy Dogg’s Doggystyle, Hole’s Live Through This
54. Steely Dan, Two Against Nature (2001)
Donald Fagen and Walter Becker’s return from a 20-year hiatus with 2000’s Two Against Nature came with their smooth, steely malevolence still intact, if not necessarily their knack for knockout choruses — the memory of the duo’s emotionally flat acceptance speech at the ’01 ceremonies is arguably more indelible than any hook here. Still, not a lot of other albums on this list could kick-off with a 1-2 like “Gaslighting Abbie” and “What a Shame About Me,” jazz-pop bops that live up to the shimmering scumminess of their titles.
Should It Haven Won? Of course not — not over Radiohead’s Kid A or Eminem’s The Marshall Mathers LP. But the better question is how it won best pop vocal album that same year, a category that nonsensically pitted the duo against *NSYNC, Britney Spears and Madonna.
Not Even Nominated: D’Angelo’s Voodoo, *NSYNC’s No Strings Attached, Rage Against the Machine’s The Battle of Los Angeles
53. Celine Dion, Falling Into You (1997)
Two tracks into Falling Into You — giving both Jim Steinman and Diane Warren arguably their greatest ’90s conduit, with “It’s All Coming Back to Me Now” and “Because You Loved Me,” respectively — and Celine had already seized the title of Canada’s greatest global superstar from Bryan Adams. The rest of the set relies too much on covers of established pop classics (“All By Myself,” “River Deep, Mountain High”) to scale the same heights, though there’s gems to be found in the album’s deeper corners, like the reggae-tinged “Make You Happy” and the smoldering title track.
Should It Have Won? Nope nope. The Grammys finally snapped out of their mid-’90s malaise with their strongest group of nominees that decade — including Smashing Pumpkins’ brilliantly overstuffed Mellon Collie and the Infinite Sadness, Beck’s brain-burstingly creative Odelay, The Fugees’ cinematic masterpiece The Score, and the peak ’90s R&B star summit of the Waiting to Exhale soundtrack — but awarded the weakest of the five.
Not Even Nominated: 2Pac’s All Eyez on Me, Fiona Apple’s Tidal, No Doubt’s Tragic Kingdom
52. Adele, 25 (2017)
If it was possible to feel bad for a universally beloved superstar in the midst of a second consecutive Grammy victory lap, you had to muster a smidge of pity for Adele at the Staples Center podium, as she literally apologized to co-nominee Beyoncé for going two for two in AOTY with her record-breaking 25. True that the LP’s success was more about momentum than anything else: “Hello” and a first-week sales number that still feels like someone misplaced the decimal point aside, the lukewarm ballads and leaden mid-tempo numbers that comprise most of the set ensured that the ’17 Grammys were the last time we really thought about 25 all that much.
Should It Have Won? Nah, Lemonade.
Not Even Nominated: Solange’s A Seat at the Table, David Bowie’s Blackstar, Chance the Rapper’s Coloring Book
51. George Harrison & Friends, Concert For Bangladesh (1973)
The good feelings around George Harrison’s successful day-night double-header benefit concert — featuring such unbilled special guests as Ravi Shankar, Eric Clapton, and a then-reclusive Bob Dylan — resulted in it becoming the first album led by a solo Beatle to take home AOTY. Today, the set is more interesting as a historical document than a front-to-back listen, though it remains at least mildly essential for Harrison’s solo rendering of The Beatles’ “Here Comes the Sun” (in its very first live performance), and a resurgent solo mini-set from a softer-voiced Dylan, including a de-waltzed “Just Like a Woman.”
Should It Have Won? Would’ve been more fun to see it go to Nilsson’s Nilsson Schmilsson, a brilliantly eclectic set featuring three songs (“Coconut,” “Without You” and “Jump in the Fire”) that still resounded in the culture decades later — and post-Russian Doll, you can probably add “Gotta Get Up” as its fourth.
Not Even Nominated: David Bowie’s The Rise and Fall of Ziggy Stardust and the Spiders From Mars, Curtis Mayfield’s Super Fly, Aretha Franklin’s Amazing Grace
50. Jon Batiste, We Are (2022)
Children of the ’90s and ’00s might’ve gotten a nostalgic rush hearing Lenny Kravitz announce Jon Batiste’s We Are as 2022’s album of the year — a throwback to the winners of yesteryear, when the Grammys were traditionally dominated by sets from NPR-approved veteran artists who only passingly intersected with the current pop mainstream. We Are is actually a better and more exciting album than a lot of those less-than-timely LPs, though: a sporadically corny but immaculately produced and gorgeously detailed set bursting with the kind of exuberance Batiste showed in his fleet-footed Grammys performance of “Freedom.” (That song’s not one of the better ones on the album, either — try the Al Green sway and piercing falsetto of “Cry” or the Voodoo/Coloring Book difference-splitter “Adulthood” if you’re not yet convinced.)
Should It Have Won? Not really — and it’s hard to imagine it would have if so many of the blockbuster sets from pop-rap superstars (Lil Nas X’s Montero, Doja Cat’s Planet Her) and alt-pop phenoms (Olivia Rodrigo’s Sour, Billie Eilish’s Happier Than Ever) hadn’t split votes with one another.
Not Even Nominated: Chris Stapleton’s Starting Over, Halsey’s If I Can’t Have Love, I Want Power, Tyler, the Creator’s Call Me If You Get Lost
49. Quincy Jones, Back on the Block (1991)
An occasionally stilted attempt to tie together four decades of Jones’ musical history — and by extension, four decades of Black popular music — in one modernized, star-studded package. Your mileage may vary on Q’s electro-funked “Birdland” or rapper-smothered title track, but “Secret Garden (Sweet Seduction Suite)” is as good as R&B tag teams get, and for better or worse, the album’s old-meets-new, ensemble-cast aesthetic would provide the template for countless Grammy darlings to follow.
Should It Have Won? An argument to be had, though soaring self-titled debuts from Wilson Phillips and Mariah Carey and MC Hammer’s game-changing Please Hammer Don’t Hurt ‘Em — the category’s first-ever hip-hop nominee — would’ve certainly been more timely choices.
Not Even Nominated: Sinéad O’Connor’s I Do Not Want What I Haven’t Got, Public Enemy’s Fear of a Black Planet, Garth Brooks’ No Fences
48. Frank Sinatra, September of My Years (1966)
The British Invasion must have really made the old guard feel their years in the mid-’60s, inspiring the 49-year-old Sinatra to record an album as maudlin as if he was rapping on death’s door, rather than one still 15 years removed from his final AOTY nomination. At the very least, the set’s lush melancholy is as specifically evocative as any album on the list, and it spawned “It Was a Very Good Year,” one of the most immaculate recordings of the entire 20th century.
Should It Have Won? Eh. For a while there in the mid-’60s, Sinatra was holding The Beatles off from their first win like the Celtics denying LeBron his finals debut — though in ’66, squaring off against the inconsistent Help! soundtrack, Ol’ Blue Eyes probably didn’t even need to go to seven games.
Not Even Nominated: Bob Dylan’s Highway 61 Revisited, John Coltrane’s A Love Supreme, Herb Alpert & Tijuana Brass’ Whipped Cream and Other Delights
47. Beck, Morning Phase (2015)
A lovely acoustic about-face from the crown prince of slack, only diminished in novelty because he’d already pulled that gambit once before. The songwriting, performance and production are all undeniably strong, and it’s about the least-likely album you could imagine to earn any kind of significant backlash — but then one night in 2016, Prince called Beck’s name instead of Beyoncé’s, Kanye came one step away from grabbing the microphone in protest, and the guy who wrote “MTV Makes Me Wanna Smoke Crack” learned what it feels like to officially be part of the establishment.
Should It Have Won? Nah, Beyoncé.
Not Even Nominated: Frozen Soundtrack, Sia’s 1000 Forms of Fear, The War on Drugs’ Lost in the Dream
46. Santana, Supernatural (2000)
About as paradigmatic an album as has been released in the last 20 years — countless older artists looking to scope the next generation for a vitality boost have been said to be “pulling a Supernatural” in the decades since. Few of them discover this much genuine electricity, though: not just “Smooth” and “Maria Maria” but also the Lauryn Hill-devised grimy soul of “Do You Like the Way” and even the Dave Matthews-featuring blues shuffle of “Love of My Life.” Only in the album’s largely guest-less final third does Supernatural really lose its magic.
Should It Have Won? The Chicks’ Fly could certainly give it a run for its money — a much earthier and less spectral set that nearly matched Supernatural RIAA certification for RIAA certification — and, well, Backstreet Boys’ Millennium has “I Want It That Way” on it, so….
Not Even Nominated: Britney Spears’ …Baby One More Time, Moby’s Play, The Roots’ Things Fall Apart
45. Glen Campbell, By the Time I Get to Phoenix (1969)
The first country album ever to win the night’s biggest award, thanks to the knockout combination of writer Jimmy Webb’s astutely economic songwriting — the title track might be the greatest pop song ever written to not even attempt a chorus — with producers Al De Lory and Nik Venet’s sighing strings and Campbell’s singularly pristine tenor. The highlights are mostly on the A-side, but despite the heavy arrangements, the set never quite drags — and at a scant 24:31 it’s easily the shortest-running of the 60 AOTY recipients.
Should It Have Won? Simon & Garfunkel’s Bookends certainly aims and mostly hits higher, and it’s a little unsportsmanlike that Campbell’s set beat the duo with a cover of their “Homeward Bound” on its tracklist.
Not Even Nominated: Otis Redding’s The Dock of the Bay, Johnny Cash’s At Folsom Prison, The Band’s Music From Big Pink
44. Christopher Cross, Christopher Cross (1981)
The captain of the good ship Yacht Rock as the ’70s cruised into the ’80s, Christopher Cross’ name became so synonymous with the pre-MTV ’80s that becoming the first artist to sweep the Grammys’ Big Four categories (album, song, record, new artist) ultimately ended up working against him. Despite its punchline status, the album’s a winner: the two big singles would be definitively transportive even if they weren’t literally about transportation, and little flourishes like the cheek-popping percussion on “Never Be the Same” or Eagles backing vocals on “The Light Is On” ensure the waters are smooth throughout. (Until the closing iceberg that is “Minstrel Gigolo,” anyway.)
Should It Have Won? Well see, there’s your trouble: Cross’ album was totally fine, but it felt a little slight to take down Pink Floyd’s titanic rock opera The Wall, not to mention late-period highs from Frank Sinatra (Trilogy) and Barbra Streisand (Guilty), the two most decorated artists of the Grammys’ first decade.
Not Even Nominated: The Clash’s London Calling, The Pretenders’ The Pretenders, Diana Ross’ Diana
43. Blood, Sweat & Tears, Blood Sweat & Tears (1970)
Despite only making it to the Billboard Hot 100’s runner-up spot with each of its three big singles — the lone album in chart history with three No. 2-peaking hits on it — Blood, Sweat & Tears stood triumphant at the end of the ’70 Grammys, held as a model of the era’s cross-everything utopianism. (“They have spanned the generation gap, the communication gap, the credibility gap, the sex gap and, yeah baby, the color gap,” host Sammy Davis Jr. raved.) That rep evaporated almost immediately following the ceremonies, but their self-titled album traverses an impressive amount of ground from jazz-funk fusion to Erik Satie, and those three anchoring hits prevent it from ever wandering too far afield.
Should It Have Won? Over Abbey Road? Not on your life. And speaking of cross-everything utopianism, The 5th Dimension’s The Age of Aquarius was both hippier and dippier — and had the better Laura Nyro-penned smash.
Not Even Nominated: Dusty Springfield’s Dusty in Memphis, The Who’s Tommy, Sly & The Family Stone’s Stand!
42. Herbie Hancock’s River: The Joni Letters (2008)
Still perhaps the only truly genuine “Wait, really, me?” reaction in Grammys televised history, 67-year-old Herbie Hancock became the 2000s’ least-likely AOTY recipient for his compilation of Joni Mitchell covers, and was so stunned he didn’t even notice when his prepared remarks fell out of his jacket pocket onstage. Maybe less shocking when you consider the guest list Hancock padded the album with — River became the third winner in six years to feature Norah Jones’ voice on the opening track — and that, well, it’s a pretty cool thing to get Tina Turner and Leonard Cohen stepping out of their comfort zones to bless meticulously arranged piano-led renditions of Joni deep cuts.
Should It Have Won? Not quite: Amy Winehouse’s Back to Black probably was front in line for those honors, with Kanye West’s Graduation right behind.
Not Even Nominated: M.I.A.’s Kala, Rihanna’s Good Girl Gone Bad, Taylor Swift’s Taylor Swift
41. Henry Mancini, Music From Peter Gunn (1959)
The first-ever album of the year, courtesy of the soundtrack to a TV show no one remembers anything else about. The jazzy set remains iconic for its rock-edged theme, still menacing enough to soundtrack an extended Sopranos cops-and-robbers sequence decades later, but its gentler side is where it really shines, courtesy of serenely stereophonic (and appropriately titled) compositions like “Dreamsville” and “Softer Sounds.” That’s a young John Williams on piano, by the way, a nominee-to-be on his own for the Star Wars soundtrack two decades later.
Should It Have Won? Probably, though let’s take a moment in honor of nominee Van Cliburn, a pianist whose rendition of Tchaikovsky’s “Concerto No. 1 in B Flat Minor” was resounding enough that even at the height of Cold War paranoia, he still won the first-ever Tchaikovsky International Competition, as an American on Soviet soil.
Not Even Nominated: The Music Man Original Cast Recording, Bo Diddley’s Bo Diddley, John Coltrane’s Blue Train
40. Bruno Mars, 24K Magic (2018)
Easily the safest pick of the five AOTY nominees in 2018, Bruno Mars didn’t realize as he blithely strolled to the stage to accept his final of six Grammys that it wasn’t just four of his peers he was battling with, but an entire culture fed up with the Recording Academy taking the easy way out. Nonetheless, no one could really fault the craft on display with 24K Magic, a brilliantly studied and executed ode to Reagan-era R&B that’s too busy having a good time to worry about being self-conscious — both to its credit and its detriment.
Should It Have Won? No sir. This should’ve been Kendrick’s year.
Not Even Nominated: SZA’s Ctrl, Ed Sheeran’s ÷, A Tribe Called Quest’s We Got It From Here… Thank You 4 Your Service
39. Robert Plant & Alison Krauss’ Raising Sand (2009)
Forget Jimmy Page and Jeff Beck — it was bluegrass-country singer-songwriter Alison Krauss that totemic rock frontman Robert Plant had to hook up with before the Grammys decided to start taking him seriously. Their Raising Sand is mighty in its own way, finding its power in nuance rather than blunt force, with even Plant’s banshee roar transmuted into a weapon of impressive texture and captivating fragility. The Gods need paintbrushes as well as hammers, apparently.
Should It Have Won? About that — shade and subtlety is all well and good, but when it’s going against Lil Wayne’s Tha Carter III and Radiohead’s In Rainbows, it’s got an uphill battle ahead.
Not Even Nominated: Vampire Weekend’s Vampire Weekend, T.I.’s Paper Trail, Katy Perry’s One of the Boys
38. Various Artists, O Brother Where Art Thou? Soundtrack (2002)
A fun game in the early ’00s: Find someone with no knowledge of O Brother Where Art Thou?, play them this soundtrack, and have them guess what led this collection of early 20th-century folk standards and covers to becoming a Grammy-winning, eight-times-Platinum phenomenon. Not that knowing it was the soundtrack to a modestly successful cult comedy really makes it that much more logical, though — so maybe just chalk it up to T Bone Burnett’s curatorial expertise in getting these crackling Dust Bowl jams to connect with 21st-century audiences. BTW, “Man of Constant Sorrow” might’ve been the breakout hit, but it’s the a cappella numbers that are the real slappers, particularly Gillian Welch, Emmylou Harris and (again) Alison Krauss’ insidious siren rendition of “Didn’t Leave Nobody But the Baby.”
Should It Have Won? Good showing from all involved, but ain’t nobody dope as Stankonia-era OutKast.
Not Even Nominated: Jay-Z’s The Blueprint, Daft Punk’s Discovery, Alicia Keys’ Songs in A Minor
37. OutKast, Speakerboxxx/The Love Below (2004)
And here we have OutKast’s member-split follow-up to Stankonia, one of the most anticipated albums of the 21st century — a set 50 percent of the way to an AOTY win before we ever heard a second of it, and at least 80 percent there once we heard all 3:55 of “Hey Ya!” To say the full double LP fell well short of the mark would perhaps be uncharitable, given that any album short of the hip-hop Sign O’ the Times would have, but… well, that’s still kind of what happened. Big Boi’s half was solid but unspectacular, Andre 3000’s half was sporadically transcendent and frequently nauseating, and Speakerboxxx/The Love Below fulfilled its commercial potential while simultaneously leaving a practically invisible footprint on pop culture once its two lead singles faded from view.
Should It Have Won? Justin Timberlake’s Justified was certainly a worthier set, but it feels wrong to strip hip-hop of one of its just two ever AOTY winners, so let’s give it instead to Missy Elliott’s Under Construction — one of just a handful of ’00s LPs with a lead single as instantly immortal as “Hey Ya!,” and with a much stronger foundation to support it.
Not Even Nominated: Linkin Park’s Meteora, 50 Cent’s Get Rich or Die Tryin’, Beyoncé’s Dangerously in Love
36. Barbra Streisand, The Barbra Streisand Album (1964)
Already a star from her Broadway career, Streisand’s recording debut at the age of 20 was anticipated enough that she could afford to put a “The” in front of it. She lived up to it with a selection of mostly lesser-known standards by beloved songwriters, allowing her own voice to soar without having to compete with the ghosts of legends before her. Streisand delivers the songs with an actor’s precision — every lyric feels like a choice, implying character and intent — and with an old showbiz salt’s command, despite standing as the youngest AOTY recipient for over three decades to come.
Should It Have Won? Yes, and given two of the nominees that year were the Swingle Sisters and the Singing Nun, can’t say Babs really had to break much of a sweat doing so.
Not Even Nominated: Bob Dylan’s The Freewheelin’ Bob Dylan, Booker T & the MGs’ Green Onions, Little Stevie Wonder’s The 12-Year-Old Genius
35. Lionel Richie, Can’t Slow Down (1985)
Thriller lite in pretty much all important respects, though obviously in the early-mid ’80s, that was still a pretty cool thing. The title wasn’t literally true, certainly — Richie would soon become synonymous with ballads like “Hello” and “Penny Lover” — but the album does tend to pick up as the pace does, especially on the underrated title track and the euphoric “All Night Long (All Night),” which survived a brief end-of-century cultural aversion to ’80s horns to become the MJ-caliber party standard it always deserved to be.
Should It Have Won? Not in 1985, no — the previous year had set a new standard for LPs as commercial behemoths, and the nominees this year reflected it: Tina Turner’s Private Dancer, Cyndi Lauper’s She’s So Unusual, Bruce Springsteen’s Born in the U.S.A., and the best of the bunch, Prince & the Revolution’s Purple Rain.
Not Even Nominated: Van Halen’s 1984, Sade’s Diamond Life, Run-D.M.C.’s Run-D.M.C.
34. Toto, Toto IV (1983)
Even more than Christopher Cross, Toto would come to be mocked for their Grammys sweep with Toto IV, vilified as soulless studio musicians impinging on the boundless sonic creativity and visual flair of new wave’s peak years. Never mind that Toto IV was essentially straight heat, from the jazz-rock strut of “Rosanna,” through to the quiet storm power balladry of “I Won’t Hold You Back” and even the unsettling pop-rock grooving of “It’s a Feeling.” Toto would of course have the last laugh in perpetuity: Today, “Africa” alone has racked up more Spotify spins than the all the tracks on the other four nominees combined.
Should It Have Won? A strong maybe: the post-Boomer anxiety rock of Billy Joel’s The Nylon Curtain and the Windexed soul-pop of Donald Fagen’s The Nightfly also make unignorable claims.
Not Even Nominated: The Human League’s Dare!, Duran Duran’s Rio, Richard and Linda Thompson’s Shoot Out the Lights
33. John Lennon & Yoko Ono, Double Fantasy (1982)
Unlikely that any of the four other nominees bothered preparing much of a speech at the 1982 Grammys, since John Lennon’s tragic murder in December of 1980 more or less guaranteed that his final non-posthumous LP would take home top honors. Context aside, it’s an impressively rich listen: Lennon’s goopy love songs “Woman” and “(Just Like) Starting Over” understandably got the chart traction, but the set’s real meat is in the gritted-teeth blues rock of his “I’m Losing You” and the spiky new wave of Yoko’s “Kiss Kiss Kiss.”
Should It Have Won? Quincy Jones’ The Dude and Steely Dan’s Gaucho are two very different types of slick, but enjoyable as those sets may be, this award was always Lennon’s and Ono’s and that’s fine.
Not Even Nominated: Talking Heads’ Remain in Light, Stevie Nicks’ Bella Donna, The Go-Go’s’ Beauty and the Beat
32. Judy Garland, Judy at Carnegie Hall (1962)
A live tour de force from a concert billed as “The Greatest Night in Entertainment History.” Following a somewhat rocky 1950s, Live at Carnegie Hall catches Garland back on the upswing, but still smarting some from the sting of the down years — an anecdote about being called fat in the U.K. paper feels telling — and motivated to deliver standards like “That’s Entertainment” and “The Man That Got Away” as if her career depended on it. Only the extended vamping and applause breaks interrupt the spell of one of the all-time showbiz greats hard at work; by the 28th time you hear the horn riff from “Over the Rainbow,” you may start praying for a tornado to sweep through the orchestra.
Should It Have Won? The West Side Story film soundtrack, though. Tough one.
Not Even Nominated: Etta James’ At Last!, Bobby Bland’s Two Steps From the Blues, Joan Baez’s Joan Baez
31. Frank Sinatra, Come Dance With Me! (1960)
While most of Frank Sinatra’s Grammy-approved sets have been of the more dolorous, meditative variety, Come Dance With Me! has nearly as much energy as a Ramones album: a dozen tracks of tempo-pushing drums and horns that stab and puncture like guitar licks, as the Chairman directs you to the floor like an overexcited house DJ. Even the sad songs have pep — “Saturday Night (Is the Loneliest Night of the Week)” zips along just like all the songs about dancing — and the only letup comes when the set collapses over the finish line with closer “The Last Dance.” Fun stuff.
Should It Have Won? Probably not, just because of Harry Belafonte’s Live at Carnegie Hall album — a set as masterful as Garland’s, and predating it by about a year, setting the standard for the live album in general.
Not Even Nominated: Miles Davis’ Kind of Blue, Chuck Berry’s Chuck Berry Is on Top, Marty Robbins’ Gunfighter Ballads and Trail Songs
30. Phil Collins, No Jacket Required (1986)
The further we get from the mid-’80s, the more manic Phil Collins’ No Jacket Required sounds in retrospect — an album of frenetic drum machines, blaring synths and horns, and overcaffeinated vocals, all seemingly bouncing around that big bald head of Collins’ like a bunch of randomly firing neurons. It adds up to one of the most memorable pop blockbusters of the decade — and far more musically and emotionally complex than the Patrick Batemans of the world would have you believe — though it might make you worry about just what kind of jacket Phil’s saying isn’t necessary in the title.
Should It Have Won? Yep, though if you’re purely talking highest highs, Whitney Houston might have Phil beat.
Not Even Nominated: Tears For Fears’ Songs From the Big Chair, Madonna’s Like a Virgin, Kate Bush’s Hounds of Love
29. Billy Joel, 52nd Street (1980)
The pressure was on for Billy Joel to follow up his 1977 best-seller The Stranger, but no man lacking in confidence has ever written a first verse — or an opening riff — like those of 52nd Street opener “Big Shot.” That one and “My Life” were the only real signature smashes off this one, but even if its starting lineup wasn’t quite as overpowering as The Stranger‘s, its bench was deeper, particularly with the sparkling fusion of “Rosalinda’s Eyes,” the Spectorian drama of “Until the Night” and the jaunty Ray Charles impersonation of the title track.
Should It Have Won? Not over Queen of Disco Donna Summer’s era-capping masterwork Bad Girls, no.
Not Even Nominated: Michael Jackson’s Off the Wall, The Knack’s Get the Knack, Rickie Lee Jones’ Rickie Lee Jones
28. Norah Jones, Come Away With Me (2003)
The first artist since Christopher Cross to sweep the Grammys’ Big Four — though Jones only walked away with three of the trophies herself, since she didn’t write her song of the year winner “Don’t Know Why” — and proof that you never know where truly untapped commercial niches lie. The Diamond-certified Come Away With Me became synonymous with Starbucks pop and unchallenging vibe playlists, but it’s closer to the Trinity Session of the ’00s: intimate performances with absolutely gorgeous acoustics and a killer Hank Williams cover.
Should It Have Won? Yeah, why not. There’s only one Come Away With Me, and everyone else nominated that year (The Chicks, Eminem, Nelly, Bruce Springsteen) was arguably more deserving for earlier works anyway.
Not Even Nominated: Wilco’s Yankee Hotel Foxtrot, Coldplay’s A Rush of Blood to the Head, Avril Lavigne’s Let Go
27. Arcade Fire, The Suburbs (2011)
Indie rock’s moment of triumph at the Grammys, for an album whose reach was great enough that it almost had to break through above ground. The set’s grand theatrics get a little exhausting over the course of 64 minutes, but it’s worth the emotional energy to scale the heights of mountainous two-parters like “Half Light” and “The Sprawl” — and besides, overwhelming endlessness is kinda the point anyway. In 2011, you could at least sorta vaguely trace a trajectory for Arcade Fire that paralleled U2 in their first seven years. Then America decided it preferred Mumford & Sons.
Should It Have Won? Oof, over Lady Gaga’s The Fame Monster? Depends on how you prefer your high-concept drama and glistening artifice, s’pose.
Not Even Nominated: LCD Soundsystem’s This Is Happening, The Black Keys’ Brothers, Sade’s Soldier of Love
26. The Chicks, Taking the Long Way (2007)
The Chicks finally broke through on their third AOTY nomination, though it essentially cost them their country career, following their refusal to, well, make nice after polarizing America with their anti-George W. Bush comments. But while there’s certainly righteous fury to be found on the Rick Rubin-produced Taking the Long Way, it’s only one of many shades the album has to offer — “Baby Hold On” does Beatlesque better than anyone since Britpop, and “Lullaby” is an acoustic tearjerker that undoubtedly forced a then-teenage Taylor Swift to step her own game up.
Should It Have Won? Justin Timberlake set the pre-Gaga standard for 21st-century pop with his FutureSex/LoveSounds — but even he had to know this was a shut-up-and-sing year for anyone not named The Chicks.
Not Even Nominated: Mary J. Blige’s The Breakthrough, Beyoncé’s B’Day, TV on the Radio’s Return to Cookie Mountain
25. Simon & Garfunkel, Bridge Over Troubled Water (1971)
Both a commercial culmination and a not-so-fond farewell for the most popular duo of the late ’60s. For such an established classic, Bridge Over Troubled Water is actually kind of a mess, with soaring near-hymnals like “The Boxer” and the title track interspersed with silly trifles like “Baby Driver” and “Keep the Customer Satisfied” (and “So Long, Frank Lloyd Wright,” which valiantly tries to split the difference between the two). It’s not surprising which side the album is better remembered for, though, and the end product is doubtless one of the most unforgettable albums of its era anyway.
Should It Have Won? Probably, though looking at the list of other nominees gives the appearance of S&G passing the torch to the next generation, including early works from James Taylor, Crosby Stills & Nash and Elton John.
Not Even Nominated: Neil Young’s After the Gold Rush, Van Morrison’s Moondance, James Brown’s Sex Machine
24. Daft Punk, Random Access Memories (2014)
The first electronic album to win AOTY, at the height of the EDM era — except RAM wasn’t really EDM at all, but rather an ambitious disco-funk throwback (with a ’70s pop and ’00s indie guest list) that probably qualifies as “rootsy” by Daft Punk’s standards. The album’s not perfect, but it does get better the more you lose yourself to prog and dive into sprawling odysseys like “Touch” and “Motherboard.” The French house duo proved that true innovators never pat themselves on the back for being ahead of the curve — and were rewarded with the biggest hit of their career for it.
Should It Have Won? It’d be a lot easier to have this discussion if Kendrick Lamar had already won for one of his other albums already, but the fact that debut good kid, m.A.A.d city just marked the beginning of his three-album losing streak makes it a tough ‘un.
Not Even Nominated: Disclosure’s Settle, Kanye West’s Yeezus, Lorde’s Pure Heroine
23. Taylor Swift, Fearless (2010)
In retrospect, it’s pretty incredible that an institution as stodgy as the then-Recording Academy — coming off a back-half-of-the-’00s run of rewarding Ray Charles, U2, The Chicks, Herbie Hancock and Robert Plant/Alison Krauss — were able to see 20-year-old Taylor Swift for who she already was: one of the most important singer-songwriters of her generation. Following her pop crossover, Fearless tends to get overlooked a little in terms of the great leap forward it represented at the time. But it brought country into the bedrooms of teen girls who might’ve rocked out to Avril Lavigne and Michelle Branch earlier in the decade, and showcased not only the pop chops that would get bigger but the storytelling instincts that would get better — in the same smash hit songs, no less.
Should It Have Won? Big showing for pop in 2009, but neither Lady Gaga (The Fame) or Beyoncé (I Am… Sasha Fierce) were represented with their best works, so probably.
Not Even Nominated: Maxwell’s BLACKsummers’night, Florence + the Machine’s Lungs, any act from the Just Like Heaven lineup
22. Whitney Houston / Various Artists, The Bodyguard Soundtrack (1994)
Half the best Whitney Houston album of her career, and half… other stuff. A-side’s what’s important: Covers of Dolly Parton and Chaka Khan elevate the originals to levels that entire generations of reality competition contestants would attempt in vain to emulate, while “I Have Nothing” and “Run to You” prove that Whitney is perfectly capable of her own first drafts as well. Don’t sleep on “Queen of the Night” or “Jesus Loves Me,” either, diversions that make you wonder about an alternate timeline where ’90s Whitney becomes a diva house siren or a pop-gospel roof-raiser.
Should It Have Won? Sure, though if you prefer your emotional catharsis a little more restrained and funereal, R.E.M.’s Automatic For the People would also have been a fair vote.
Not Even Nominated: Dr. Dre’s The Chronic, Liz Phair’s Exile in Guyville, Janet Jackson’s janet.
21. Kacey Musgraves, Golden Hour (2019)
Kacey Musgraves is all right with a slow burn, and apparently so were the 2019 Grammys: After three consecutive chart-slaying, Big Pop winners from Taylor Swift, Adele, and Bruno Mars, the Recording Academy elected one of its most patient and deliberate AOTY winners in Golden Hour. That’s not to say that the set is too understated to be transcendent, though — rather, it just finds the sublime in the quotidian, whether on the sighing FOMO anthem “Lonely Weekend” or the stomping anti-anti-hero ballad “High Horse.” A refreshing reminder that occasionally songcraft nuance and emotional shading can be the stuff of mass consensus, too.
Should It Have Won? Matter of preference, really — Cardi B’s Invasion of Privacy and the Kendrick Lamar-stewarded Black Panther soundtrack were both more explosive and vital, but maybe didn’t have the emotional lock-and-key effect that Golden Hour had with the hearts of many.
Not Even Nominated: Ariana Grande’s Sweetener, St. Vincent’s MASSEDUCTION, Travis Scott’s Astroworld
20. Paul Simon, Graceland (1987)
Take a second to wince at the thought of this album coming out in 2019, as claims of appropriation and outright thievery plagued Graceland upon its release, and undoubtedly would overwhelm the album today. Fair play, though the songs themselves hold up: lithe and lively creations with enough bursts of pop in dazzling technicolor that it gave Paul Simon’s sagging career an unlikely third wind, and spiked international interest in musical genres like zydeco and mbaqanga. Wasn’t at the expense of Simon’s songwriting, either — the title track is a coming-of-middle-age road-tripper worthy of its own Alexander Payne adaptation, and “You Can Call Me Al” is “Once in a Lifetime” with a half-backwards bass solo and better horns.
Should It Have Won? Maybe not, since Janet Jackson’s star-making, mold-breaking Control was also in the mix — and while Simon had already won twice, Ms. Janet was somehow never nominated again.
Not Even Nominated: Run-D.M.C.’s Raising Hell, Bon Jovi’s Slippery When Wet, Anita Baker’s Rapture
19. Billie Eilish, When We All Fall Asleep, Where Do We Go? (2020)
By the time of the 2020 ceremonies, Billie Eilish’s impending Grammy supremacy was expected enough for news of it to be met with a thunderous “duh.” But let’s not lose sight of what a unique beast When We All Fall Asleep, Where Do We Go? really was: not just a mainstream-barnstorming alt-everything blockbuster that felt generational the day it was released, but also a silly, revealing and charmingly awkward album made by a 17-year-old singer-songwriter and her knob-twiddling older brother, as much inside joke as defining statement. That Eilish has already scored as many hits in the year following her Big Four sweep as Christopher Cross did in the decades following his is also unsurprising.
Should It Have Won: Well, Billboard‘s staff did name Ariana Grande’s career-culminating achievement Thank U, Next its No. 1 album of 2019 — but Billie was right behind her at No. 2, so we can more or less call it a draw.
Not Even Nominated: Tyler, the Creator’s IGOR, Lady Gaga & Bradley Cooper’s A Star Is Born Soundtrack, Jonas Brothers’ Happiness Begins
18. Alanis Morissette, Jagged Little Pill (1996)
A decade before Taylor Swift (and two before Billie Eilish), another young singer-songwriter whose hurricane-force sweeping through pop culture proved undeniable, even at the height of the Grammys’ backwards-looking MTV Unplugged era. Jagged Little Pill isn’t always the easiest to swallow, but its brazen confidence feels even more staggering with each passing year: It may or may not have been the first AOTY to use the “F” word, but it was certainly the first that really meant it. The album could be as sweet as it was furious, though, or as confused, or as tickled pink — or all of them at once, as in “Hand in My Pocket” — which is probably why teenagers took to it by the millions, since adolescence is really never just one thing.
Should It Have Won? Yep, though shoutout to Joan Osborne’s Relish, because it’s a good album and when else were you going to think about Joan Osborne’s Relish this month?
Not Even Nominated: PJ Harvey’s To Bring You My Love, Nirvana’s MTV Unplugged in New York, TLC’s CrazySexyCool
17. Stevie Wonder, Fulfillingness’ First Finale (1975)
It says something about Stevie Wonder’s ’70s run that an album like Fulfullingness could be considered the Other Stevie Wonder Album from the period. It’s true that the set is a little less organized and doesn’t quite have the enduring radio classics of its brother LPs, but what’s here is still breathtaking: “Heaven Is 10 Zillion Light Years Away” is a woozy dreamer that feels like an early model for Frank Ocean’s Blond period, and “They Won’t Go When I Go” is a ballad overpowering enough to either work as a protest song or a eulogy. Plus, don’t forget about the hit singles that are here: “You Haven’t Done Nothin'” is an incendiary Nixon invective whose drums are practically hissing in fury, and Stevie sounds too giddy on “Boogie on Reggae Woman” to bother pronouncing his consonants.
Should It Have Won? Three-way tossup between FFF, Paul McCartney & Wings’ Band on the Run and Joni Mitchell’s Court & Spark.
Not Even Nominated: Elton John’s Goodbye Yellow Brick Road, Barbra Streisand’s The Way We Were, The Who’s Quadrophenia
16. Taylor Swift, 1989 (2016)
The first album since Adele went supernova to again get music industry people thinking, “Hm, maybe we can turn this thing around after all.” 1989 was a blockbuster the way Mom used to make ’em: Hit singles after hit singles after hit videos after tabloid headlines after damn is it really 2016 already and this album is still going? Sure was, and Taylor used her second AOTY win that February to trumpet her own historic accomplishments, while also shading Kanye West for saying some not-nice things about her on wax — wow, what a pop star. But the most remarkable thing about 1989 was that once it finally did die down, there were still singles to go: “Welcome to New York” was Devil Wears Prada-worthy enough to excuse the stretch in credibility, and “All You Had to Do Was Stay” was one of the decade’s best pop songs, straight up.
Should It Have Won? Ah, Kendrick again — this time for To Pimp a Butterfly. Call it a draw?
Not Even Nominated: Courtney Barnett’s Sometimes I Sit and Think and Sometimes I Just Sit, Twenty One Pilots’ Blurryface, D’Angelo’s Black Messiah
15. Bob Dylan, Time Out of Mind (1998)
Not just Bob Dylan’s long-awaited first AOTY win, 35 years into his legendary career — disregarding his appearance on Concert For Bangladesh, anyway — but also his first solo nomination. That’s one for the history books to try to explain, but at least when it came time for his long-overdue makeup call, Dylan won for an album as worthy as most of his ’60s and ’70s classics: Time Out of Mind was the arresting sound of a singer-songwriter entering his final act with eyes wide open, scared and vulnerable but not naive or intimidated. “Standing in the Doorway” and “Not Dark Yet” were tearjerkers for folks too exhausted to bother weeping literal tears, while “Love Sick” was a badass vow of romantic celibacy, with a beat art-world pranksters could dance to.
Should It Have Won? If they cared, Radiohead would have a legit grievance about not receiving their own belated make-good for their generational alt-prog epic OK Computer losing here. If they cared.
Not Even Nominated: Björk’s Homogenic, The Notorious B.I.G.’s Life After Death, Erykah Badu’s Baduizm
14. Bonnie Raitt, Nick of Time (1990)
The title was undoubtedly true for the arrival of Bonnie Raitt’s late-career success, as her longtime bubbling-under-the-mainstream level of popularity had threatened to give way to outright obscurity in the mid-’80s. The most remarkable thing about Nick of Time‘s breakthrough was that it didn’t need a hit single, selling five million copies without a top 40 hit (those’d come on 1991’s Luck of the Draw) and instead becoming a pop culture force through Raitt’s sheer skill, assuredness and likability. The singer-guitarist struts around Nick like a pool shark, lining up all sorts of different looks — brawny rock, delicate balladry, bluesy soul, country, reggae — and knocking ’em in with a wink and a smile, while the rest of her underappreciated ’70s contemporaries stare on from the sidelines, befuddled at how easy she’s making it look.
Should It Have Won? Yes, though if you’ve never heard Fine Young Cannibals’ late-’80s pop sampler platter The Raw & The Cooked in full, it’s well worth a listen.
Not Even Nominated: Janet Jackson’s Rhythm Nation 1814, The Cure’s Disintegration, Beastie Boys’ Paul’s Boutique
13. Stan Getz & Joao Gilberto, Getz/Gilberto (1965)
The Birth of the Chill. Saxophonist Stan Getz and guitarist Joao Gilberto teamed up in 1964 to make bossa nova a legit worldwide phenomenon, in particular with their Astrud Gilberto-sung breakthrough single (and future pop perennial) “The Girl From Ipanema.” That’s an all-timer, obviously, but the rest of the set is similarly transfixing — you can practically hear the lighting around you dim a little more with every circulation of spit through Getz’s sax. Should probably be a third name in that title, too: Antônio Carlos Jobim, who plays piano throughout the set and also composed most of its tracks, including its most enduring tracks: “Desafinado,” “Corcovado” and “Ipanema.”
Should It Have Won? Yep, though with a double dose of Babs in the nominees — the Funny Girl original cast recording and her own People set — it’s sorta surprising it did.
Not Even Nominated: The Beatles’ A Hard Day’s Night, The Supremes’ Where Did Our Love Go, Hello Dolly! Original Cast Recording
12. Taylor Swift, Folklore (2021)
“I just need to make a better record” was Taylor Swift’s famous takeaway, as shown in her Miss Americana documentary, from being snubbed from an album of the year nomination for her lukewarmly received Reputation LP in 2018. Well, that next album (2019’s Lover) didn’t score a nod either, so in 2020 she wasn’t taking any chances: She packed up and headed to woodsy isolation (metaphorically if not literally) for the spellbinding Folklore. Though the Grammy aspirations of the more contemplative, singer-songwriter-oriented set are obvious, so is its brilliance, containing some of Swift’s strongest melodies and most evocative storytelling to date — taking on new perspectives and characters and somehow feeling even more personally revealing as a result. And don’t let the greyscale cover fool you; thanks to impressively varied (but collectively coherent) sonic shading provided by collaborators Aaron Dessner and Jack Antonoff, Folklore still bursts out of your headphones in color just as screaming as Taylor’s prior AOTY champ.
Should It Have Won? Another coin toss between our top two albums of the year, Folklore and Future Nostalgia — but we ultimately made the same call as the Grammys, so better luck next time, Dua Lipa.
Not Even Nominated: Fiona Apple’s Fetch the Bolt Cutters, Harry Styles’ Fine Line, and, well, an album by a guy you won’t be seeing at the Grammys again anytime soon
11. George Michael, Faith (1989)
For 18 months towards the end of the ’80s, George Michael was about as big of a solo star as you can be, thanks to Faith — closer to the Thriller of the decade’s second half than even MJ’s own follow-up. Not hard to see why, either: Faith doesn’t quite cohere as a full-album statement, but that’s because its half-dozen hit singles were each their own universe, singular and brilliant and bursting with possibilities for pop’s future. Having conquered the pop world, George Michael stared into his own personal abyss and decided to go acoustic the next time out — if only he’d given 1990’s Listen Without Prejudice, Vol. 1 the title GM Unplugged, he probably could’ve gone two for two on AOTY.
Should It Have Won? Undoubtedly.
Not Even Nominated: Public Enemy’s It Takes a Nation of Millions to Hold Us Back, INXS’ Kick, Leonard Cohen’s I’m Your Man
10. U2, The Joshua Tree (1988)
Rare when a band wins AOTY for the first time at the exact moment that they should, but that’s what U2 did with The Joshua Tree, a set that proved that alternative rock could be every bit as massive — in both sound and popularity — as the classic rock veterans and hair metal upstarts dominating arenas in the late ’80s. It really only needed three tracks to do it, too, each expanding the breadth of ’80s rock on its own separate axis: “Where the Streets Have No Name” blasted it out all across the open plains, “I Still Haven’t Found What I’m Looking For” elevated it all the way to the heavens, and “With Or Without You” expanded its width to include absolutely everyone.
Should It Have Won? Yikes, won’t find a much tougher Grammy showdown than Joshua Tree vs. Prince’s Sign O’ the Times. Depends on whether you prefer your expansive LP masterworks clear-skied and gleaming or murky and complicated, perhaps.
Not Even Nominated: Guns N’ Roses’ Appetite For Destruction, R.E.M.’s Document, Fleetwood Mac’s Tango in the Night
9. Adele, 21 (2012)
The thing that remains charming about 21‘s runaway success nearly a decade later was how unpredictable it still seems. It’s not the album of an artist expecting to outsell Lady Gaga and Beyoncé, it’s just the best damn breakup album made by a young singer/songwriter in eons — and it turned out that in a pop landscape then dominated by The Black Eyed Peas, Kesha and Pitbull, there was still real space for that. The best thing about 25 was how it pointed out the value of the swaths of different tones and sounds 21 offered — not just the chandelier-shaking belting of “Someone Like You” and “Set Fire to the Rain,” but the shuffling pop-soul of “He Won’t Go,” the girl-group sashay of “Rumour Has It,” even the livewire pop-rock tension of “Rolling in the Deep,” proving heartbreak need not be monolithic. There are important lessons to be learned here, though anyone but Adele trying to repeat its formula would be like flipping a quarter and attempting to get it to land on its side.
Should It Have Won? Of course — not like anyone else had a shot anyway.
Not Even Nominated: Kanye West’s My Beautiful Dark Twisted Fantasy, Nicki Minaj’s Pink Friday, Bon Iver’s Bon Iver, Bon Iver
8. Carole King, Tapestry (1972)
The album that Taylor, Adele, and all other best-selling modern singer/songwriters should probably have to kick up a certain percentage to, Tapestry created the mold for the pop-rock confessional as potential summer blockbuster. Carole King’s songwriting, already a proven commodity through countless hits for the likes of Little Eva, The Drifters and Aretha Franklin, was the main attraction, but her singing turned out to be just as important a part of the equation: Close your eyes now and picture that pause between “It would be… SO FINE” at the climax of “So Far Away” and you’ll hear her voice in its exact timbre all the way down your spine. The combination was powerful enough that even Tapestry‘s deep cuts became iconic: “You’ve Got a Friend” gave James Taylor his first Hot 100 No. 1 months later, “Where You Lead” was used as the Gilmore Girls‘ theme in the early ’00s, and “Beautiful” titled her hit Broadway musical a half-decade ago.
Should It Have Won? Yes, though Academy guilt over George Harrison’s gorgeous triple LP All Things Must Pass getting passed over may have played a part in his Concert For Bangladesh winning a year later.
Not Even Nominated: The Rolling Stones’ Sticky Fingers, Joni Mitchell’s Blue, Marvin Gaye’s What’s Going On?
7. Fleetwood Mac, Rumours (1978)
Four decades after Rumours, its creators still can’t escape the drama, pettiness and soap operatic intrigue that inspired its creation — at any moment, you can picture someone in the band listening to “I Don’t Want to Know” or “Go Your Own Way,” hearing a lyric in a new way, shouting “Hey, wait a minute!” and jumping on the phone to start the cycle anew. That’s probably the thing that keeps the album such a vital piece of the modern pop fabric, never more than a sample, sync or meme away from another generation of rediscovery. Well, that and the songs, products of a unique alchemy that allows stomping folk-rock, gauzy Laurel Canyon balladry and menacing proto-goth to all sound like it’s pumping from the same fraught central nervous system — and with enough character and conviction to make “Thunder only happens when it’s raining” and “Don’t stop thinking about tomorrow, ‘coz it’ll soon be here” sound like gospel.
Should It Have Won? Yes, though wow what a year for ’70s West Coast studio rock, with Steely Dan’s Aja and The Eagles’ Hotel California also in contention.
Not Even Nominated: Meat Loaf’s Bat Out of Hell, Bob Marley and the Wailers’ Exodus, all punk rock
6. Stevie Wonder, Songs in the Key of Life (1977)
“Most of all, I’d like to thank Stevie Wonder, who didn’t make an album this year,” was how Paul Simon concluded his acceptance speech for album of the year in 1976, following Wonder’s back-to-back wins in ’74 and ’75. His assumption that Wonder would’ve won had he participated that year was validated by Stevie winning a third time upon his return in ’77, though it wasn’t like he cruised to the finish line: Songs in the Key of Life was a 21-track, three-record set full of hit pop singles, interstellar explorations, religious conversations and everything in between, the only way a run like Wonder’s mid-’70s could’ve been capped. The best thing about Songs is the way new favorites sneak up on you with every listen; its size practically guarantees there’ll always be one unexpected track that knocks you off your feet. The true testament to its largesse was what the prolific Wonder did next: nothing, for three years, then an album about plants.
Should It Have Won? Much love to Peter Frampton and Boz Scaggs, but yeah, handily.
Not Even Nominated: Queen’s A Night at the Opera, Earth Wind & Fire’s Gratitude, Boston’s Boston
5. Bee Gees & Various Artists, Saturday Night Fever Soundtrack (1979)
Pre-Thriller, Michael Jackson was reportedly so in awe of the commercial success of the Saturday Night Fever soundtrack that he listened to it enough times to practically crawl inside of its DNA, attempting to learn its core secrets. Having the Brothers Gibb at the peak of their powers is a good start: Trim the 17 cuts on this set down to the half-dozen Bee Gees originals and it’s still a timeless classic, not to mention a hell of a starting point for a greatest hits. But Saturday Night Fever outrates The Bodyguard here because the rest is nearly as essential: Hits by disco peers KC and the Sunshine Band and the Trammps are among their era’s best, classical rewrites by David Shire and Walter Murphy are charmingly dated, and the jams farmed out to Yvonne Elliman and Tavares show that not even Reggie Jackson or Rod Carew were hitting like Barry Gibb in ’77.
Should It Have Won? For sure, though some theater folks out there might prefer the nearly-as-successful Grease soundtrack. And ten points if you knew that this was the year of The Rolling Stones’ only ever AOTY nomination, for the disco- and new wave-inflected Some Girls.
Not Even Nominated: The Cars’ The Cars, Patti Smith Group’s Easter, Funkadelic’s One Nation Under a Groove
4. Michael Jackson, Thriller (1984)
Whatever lessons Jackson learned from Saturday Night Fever, he certainly put them to work for Thriller, which rewrote the rules of the entire music industry, helped cement MTV’s place at the center of ’80s pop culture, and still remains the album all other successes are measured against. There’s nothing new to say about an LP that’s practically a genre of one, a set still more relevant to pop music 37 years after its Grammy sweep than most albums released so far this year — although following the release of the Leaving Neverland doc, it’s an album a lot of fans have had to re-evaluate their relationship with in recent years.
Should It Have Won? Big year for big albums, also including David Bowie’s Let’s Dance, The Police’s Synchronicity and even Billy Joel’s underrated-in-retrospect An Innocent Man — but yeah, sure.
Not Even Nominated: Prince’s 1999, ZZ Top’s Eliminator, Eurythmics’ Sweet Dreams (Are Made of This)
3. Lauryn Hill, The Miseducation of Lauryn Hill (1999)
So many records and firsts in one AOTY-winning album that it should probably get its own wing at the Grammy Hall of Fame, but most importantly, the first rap-based album ever to win — and 20 years later, still only one of two in that respect. Not surprising that Miseducation was the one to do it, as another work of precocious genius by a do-nearly-everything solo artist with a singular vision, one rooted in rap, but soul even more so, in the genre’s truest sense. Decades later Miseducation‘s rep continues to expand in new and interesting ways, largely because the breadth of material covered makes it feel like it almost exists outside of music: For 16 modern artists to each rave about how one of the songs affected them personally feels like an appropriate tribute to it, but so does a group of young people just getting together to talk about love and growing up and finding their truth. Too bad Songs in the Key of Life was already taken for a title.
Should It Have Won? Yes, though it’s a strong class that also includes Shania Twain’s Come on Over and Madonna’s Ray of Light — and the first AOTY race where all five nominees were female or female-fronted.
Not Even Nominated: OutKast’s Aquemini, Brandy’s Never Say Never, Elliott Smith’s XO
2. The Beatles, Sgt. Pepper’s Lonely Hearts Club Band (1968)
The first rock album to ever win the award, and the Beatles’ only win in five tries. Whether or not it’s the Fab Four’s finest set of songs is certainly up for debate, but it’s the logical breakthrough set for an institution like the Recording Academy, who probably had no shortage of members wondering when rock was gonna fade out and they could get back to voting for Judy Garland and Henry Mancini. They held on as long as they could, but Sgt. Pepper‘s credit in the straight world was too undeniable: It was rock music from the auteur’s perspective, composed and structured like a movie, and performed and produced like a symphony. Its detail still stuns today: even a three-second transition overlap between two of the album’s weaker tracks feels like it’s worth studying for weeks. It rocked, too, but that was almost beside the point: Sgt. Pepper proved rock’s potential for prestige, and there was no turning back from there.
Should It Have Won? Natch, but credit to Frank Sinatra for partnering with Antonio Carlos Jobim in a superteaming of AOTY alums and attempting to hold off those pesky Beatles just one more year.
Not Even Nominated: The Doors’ The Doors, Aretha Franklin’s I Never Loved a Man (The Way I Love You), The Jimi Hendrix Experience’s Are You Experienced?
1. Stevie Wonder, Innervisions (1974)
The beginning of Stevie Wonder’s dynastic run of three consecutive albums of the year, and understandably so: Simply put, it’s the consummate album of the year. It’s a breakthrough work of prodigious genius from an artist entering their prime. It feels neatly organized and conceptually united, but still has hit singles that live on outside of its larger context. It speaks to the personal, the cultural, the political, the universal. It’s rooted in classic pop, rock and soul, but pushes into the future both sonically and thematically. It’s got specific moments that unexpectedly pop into your head just as you’re living your life (“New York! Just as I pictured it… skyscrapers and everything!”). It’s got a dope album cover. Most importantly, it feels accessible to just about everyone, while still remaining a clear statement of one man’s perspective. And on a list like this, there’s no spot that’s too high for that.
Should It Have Won? Seems like it.
Not Even Nominated: Pink Floyd’s The Dark Side of the Moon, Al Green’s Call Me, Carly Simon’s No Secrets