Since 1959, the National Academy of Recording Arts and Sciences has awarded the greatest achievements in music. Originally called the Gramophone Awards, the Grammys have become synonymous with the most important and influential figures in the music industry—be it artists, producers, record execs or labels. The Recording Academy has recognized 66 LPs for Album of the Year, beginning with Henry Mancini and including some of the greatest bands and singers of all time—including the Beatles, Taylor Swift, Whitney Houston and Frank Sinatra. However, the Recording Academy rarely gets their pick for Album of the Year correct. Last night, they awarded Bad Bunny for his 2025 LP DeBí TiRAR MáS FOToS, so we thought it would be right to take a look at all 68 winners and deduce who should have come out on top every year since 1959. From Vaughn Meader to Harry Styles to Alanis Morissette to Fleetwood Mac, here is every Album of the Year winner ranked from worst to best.
68. Vaughn Meader: The First Family (1963)
Should’ve Won: Ray Charles, Modern Sounds in Country and Western Music
It’s going to become clear that, for the first decade of the Grammys’ existence, they awarded their most coveted prize to some pretty suspect albums. But, you also have to take into account that, between 1959 and 1969, it was rare to see mainstream rock or R&B albums outmuscle jazz, showtunes, and pop traditional records in critical categories. In 1963 though, comedian Vaughn Meader winning over Ray Charles might go down as one of the biggest WTF moments in Grammy history.
67. Bob Newhart: The Button-Down Mind of Bob Newhart (1961)
Should’ve Won: Nat King Cole, Wild Is Love
The first comedy album to win Album of the Year, The Button-Down Mind of Bob Newhart isn’t music at all. The fact that it won over something like Nat King Cole’s Wild Is Love or Harry Belafonte’s Belafonte Returns to Carnegie Hall is a mark of ignorance in ways a list like this couldn’t even begin to dissect.
66. Henry Mancini The Music from Peter Gunn (1959)
Should’ve Won: Ella Fitzgerald, Sings the Irving Berlin Songbook
The first album to ever win Album of the Year, The Music from Peter Gunn is a TV series score and has no business here. But, Henry Mancini is a compositional legend, and he cropped up a lot in the nomination fields for the first handful of Grammy ceremonies. Ella Fitzgerald’s Sings the Irving Berlin Songbook is one of the best jazz vocal albums ever. You do the math.
65. Frank Sinatra: A Man and His Music (1967)
Should’ve Won: The Beatles, Revolver
Frank Sinatra won three Album of the Year awards in his lifetime and, while he is one of the most important entertainers in music history, no one on this planet should be trying to debate why A Man and His Music winning over Revolver was the correct call.
64. Frank Sinatra: Come Dance with Me! (1960)
Should’ve Won: Harry Belafonte, Belafonte at Carnegie Hall
Come Dance with Me! is better than A Man and His Music, but it’s not better than Belafonte at Carnegie Hall.
63. Quincy Jones & Various Artists: Back on the Block (1991)
Should’ve Won: Wilson Phillips or Mariah Carey
I love Quincy Jones and, with 28 victories, he is among the most-decorated Grammy Award nominees ever. But his album Back on the Block, which features performances from Ella Fitzgerald, Miles Davis, Dionne Warwick, Chaka Khan, Ray Charles, and Bobby McFerrin (just to name a few), wasn’t better than Mariah Carey or Wilson Phillips’ self-titled debut albums, especially the latter.
62. Herbie Hancock: River: The Joni Letters (2008)
Should’ve Won: Amy Winehouse, Back to Black
Herbie Hancock is a living legend, there’s no doubt about it; Head Hunters is one of the greatest jazz records of all time. His 2008 Album of the Year-winning LP, River: The Joni Letters, is a sweet tribute to Joni Mitchell but a lackluster pick for the top prize on music’s most important night, especially when Amy Winehouse’s Back to Black was right there. Kanye West’s Graduation would have also made for a solid pick. Sometimes the Recording Academy leans too heavily on their own inclinations to award safe bets. Things haven’t changed much since 2008, really, though the 2000s really was a Dark Period in the Academy’s run.
61. Ray Charles & Various Artists: Genius Loves Company (2005)
Should’ve Won: Kanye West, The College Dropout
On paper, it’s hard to argue against giving the award to Ray Charles for his final studio album. Artists like Natalie Cole, Elton John, Van Morrison, and Willie Nelson were brought in to help complete the songs with Charles, and it’s a seminal swan song for the greatest male R&B vocalist of all-time. But can we really say it was definitively better than Kanye West’s The College Dropout? No, we can’t.
60. Norah Jones: Come Away with Me (2003)
Should’ve Won: Bruce Springsteen, The Rising
The bleak 2000s keep on truckin’, and the chokehold Norah Jones had on department store radio stations ought to be a great representation of that for generations to come. Her 2003 debut album, Come Away with Me, is a sweet little acoustic pop project. But picking it over Eminem’s The Eminem Show, the Chicks’ Home, or Bruce Springsteen’s career-revitalizing The Rising is a head-scratcher.
59. Mumford & Sons: Babel (2013)
Should’ve Won: Frank Ocean, channel ORANGE
The 2013 Grammys was the first ceremony I ever watched, and I admittedly tuned in to see Frank Ocean sweep for channel ORANGE. But he didn’t, much to my own disappointment. Instead, the top prize of the night went to Mumford & Sons for their hot dog water-sour, stomp-clap shtick Babel. The Recording Academy passed on Jack White’s Blunderbuss, the Black Keys’ El Camino, and fun.’s Some Nights, all of which would have been much smarter picks for Album of the Year. But, at the end of the day, channel ORANGE deserved this award.
58. Tony Bennett: MTV Unplugged (1995)
Should’ve Won: Bonnie Raitt, Longing in Their Hearts
It’s always a bit of a bummer to see a legend win a Grammy after their prime like this, as if the Recording Academy wants to make amends with their previous oversights before it’s too late. Tony Bennett’s MTV Unplugged album is nothing groundbreaking. Lucky for him, the field of nominees in 1995 was abysmal. The next best pick, if you’re twisting my arm, is probably Bonnie Raitt’s Longing in Their Hearts. But who cares?
57. Santana: Supernatural (2000)
Should’ve Won: TLC, FanMail
I think Supernatural is a bottom-tier Album of the Year winner if “Smooth” (featuring Matchbox Twenty’s Rob Thomas) isn’t its 15x platinum lead single. I’ll never understand why it won eight other Grammys either. TLC should have taken this one home for FanMail, though the Chicks would have been a solid pick for their album Fly.
56. Frank Sinatra: September of My Years (1966)
Should’ve Won: The Beatles, Help!
Frank Sinatra’s second Album of the Year award is his best, and September of My Years features some of his strongest tunes—“Last Night When We Were Young,” “September Song,” “This Is All I Ask.” But, glaringly, the Beatles’ Help! is one of the greatest folk-pop albums of its era. The Fab Four would get their kudos two years later, but I’d argue that they should have won all five of the Album of the Year nominations they got between 1966 and 1970. They should not have lost to Sinatra twice.
55. Dixie Chicks: Taking the Long Way (2007)
Should’ve Won: Justin Timberlake, FutureSex/LoveSounds
Before 2007, the Chicks (formerly known as the Dixie Chicks) had been nominated twice for Album of the Year and failed to net any wins. That all changed when the Recording Academy gave them the brass for Taking the Long Way, their Rick Rubin-produced LP. It’s a fine project, but their weakest as a group. This year wasn’t particularly stacked in quality, and you could argue that the success of Gnarls Barkley’s “Crazy” was massive enough to push St. Elsewhere over the edge, but I’d give the brass to Justin Timberlake for FutureSex/LoveSounds, one of the best pop records of the 2000s.
54. Barbra Streisand: The Barbra Streisand Album (1964)
Should’ve Won: The Barbra Streisand Album
The first entry on this list where the winner deserved to win, Barbra Streisand’s The Barbra Streisand Album is good but didn’t have much competition stacked up against it. This was the list of nominees alongside her: Ward Swingle & The Swingle Singers, Andy Williams, Al Hirt, and Soeur Sourire. Yawn. Babs is Babs, and I’d give this one to her every time.
53. Taylor Swift: Midnights (2024)
Should’ve Won: SZA, SOS
While the 66th Grammy Awards featured a decently strong Album of the Year field, the Recording Academy still found a way to get it wrong. You almost couldn’t make the wrong choice, and yet they did. Great records from Janelle Monáe and Olivia Rodrigo and brilliant records from SZA and Lana Del Rey were passed up in favor of perennial safe bet Taylor Swift, whose album Midnights now has the honor of being one of the weakest winners in this category since Mumford & Sons in 2013. The people’s winner—SZA’s SOS—would’ve been a bulletproof pick. Hell, even Lana’s Did you know that there’s a tunnel under Ocean Blvd, her best album yet, would have been a bold and welcomed pick.
52. Lionel Richie: Can’t Slow Down (1985)
Should’ve Won: Literally any of the other four nominated albums
This is one of the most puzzling years in Grammy history, I think. Album of the Year went to Lionel Richie for Can’t Slow Me Down. When I say that it was the weakest nominee out of the bunch, please believe me. Cyndi Lauper’s She’s So Unusual, Prince & The Revolution’s Purple Rain, Bruce Springsteen’s Born in the U.S.A., and Tina Turner’s Private Dancer were passed on for “All Night Long (All Night)” and “Hello.” You could give the award to any of the other four albums and it would be correct. If I’m picking one over the others, give me Purple Rain.
51. U2: How to Dismantle an Atomic Bomb (2006)
Should’ve Won: Kanye West, Late Registration
Bland rock and pop records beating much better rap records for Album of the Year is a 30-year-old industry tradition. The Recording Academy missed out on giving Kanye a trophy for Late Registration, though it was not an entirely compelling slate of nominees to begin with. The chokehold U2 has on the music business ought to be studied. How to Dismantle an Atomic Bomb was good but it wasn’t Album of the Year good, you know?
50. Robert Plant & Alison Krauss: Raising Sand (2009)
Should’ve Won: Radiohead, In Rainbows
Yes, Radiohead should have won this year for In Rainbows. But I think Raising Sand gets more hate than it deserves. Robert Plant and Alison Krauss are incredible together, and T Bone Burnett’s production made the duets shine even more so. But that doesn’t mean it deserved to win. Lil Wayne and Coldplay got nods for Tha Carter III and Viva la Vida or Death and All His Friends, respectively, but In Rainbows is the best record here and it’s not close.
49. George Harrison & Friends: The Concert for Bangladesh (1973)
Should’ve Won: Nilsson, Nilsson Schmilsson
A weak nomination field, I’m not mad that the Recording Academy gave it to George Harrison in 1973 for his Concert for Bangladesh album. I’d have rather seen the award go to Don McLean for American Pie or Harry Nilsson’s Nilsson Schmilsson. Even the Jesus Christ Superstar soundtrack would have been a bolder pick. But emotionally and spiritually, The Concert for Bangladesh got rewarded for being a charity record.
48. Christopher Cross: Christopher Cross (1981)
Should’ve Won: Billy Joel, Glass Houses
Let’s set things straight: Christopher Cross is not a bad album. “Sailing” alone makes certain of that. But it went up against Billy Joel’s Glass Houses and Pink Floyd’s The Wall, two projects much better than Cross’ opus could ever be. It’s a tight race between Joel and Floyd, but I’ll give it to Joel—Glass Houses is great, maybe his very best album not named The Stranger.
47. Jon Batiste: We Are (2022)
Should’ve Won: H.E.R., Back of My Mind
2022 was a solidly well-represented year and Jon Batiste’s We Are is a fine winner, whether you like it or not. Batiste is a virtuoso who makes bulletproof R&B, soul, and jazz-pop music, and he did just that on his sixth album. Olivia Rodrigo got nominated for her debut Sour, while Taylor Swift’s Evermore and Billie Eilish’s Happier Than Ever found love, too. But, if we’re talking about who should’ve won, this award belonged to H.E.R. for Back of My Mind.
46. Harry Styles: Harry’s House (2023)
Should’ve Won: Beyoncé, Renaissance
It’s one thing for the Recording Academy to give Album of the Year to Harry Styles instead of Kendrick Lamar, Brandi Carlile, and Adele. It’s another thing entirely for them to give him the award over Beyoncé. The one plus that Harry’s House has going for it is that it’s a better winner than Midnights, but that really means nothing at this point. Renaissance was a career triumph for Beyoncé and, after being snubbed three times for Album of the Year, this felt like, finally, she would get her due. And then Harry Styles won. It wouldn’t be so brutal if it wasn’t such a cycle. Renaissance, Lemonade, SOS, To Pimp a Butterfly—the list goes on and it’s exhausting. But Beyoncé will finally get her Grammy, just give it a couple years.
45. Steely Dan: Two Against Nature (2001)
Should’ve Won: Radiohead, Kid A
I don’t care how hard you argue for it, Two Against Nature winning Album of the Year over Kid A will never be right. Yes, it was Steely Dan’s comeback album after 20 years in the can, but—whether you like Radiohead or not—Kid A is one of the greatest albums of this century. And, on top of that, Beck’s Midnite Vultures and Eminem’s The Marshall Mathers LP were right there, too. Steely Dan are all-time greats, and the Recording Academy were making up for passing over Aja and Gaucho during their respective years being nominated.
44. Toto: IV (1983)
Should’ve Won: Donald Fagen, The Nightfly
One of the weaker nomination fields post-1970, Toto winning isn’t entirely a band move. Its only competition in quality was The Nightfly, and giving it to Billy Joel for The Nylon Curtain or Paul McCartney for Tug of War would have just been exhausting. “Rosanna” was a good lead single (and a Record of the Year winner), and “Africa” has remained beloved. Easy picks are easy for a reason, I guess.
43. Beck: Morning Phase (2015)
Should’ve Won: Beyoncé, Beyoncé
Nearly all of the most recent WTF choices for Album of the Year have involved Beyoncé losing, and Beck’s surprise win over her self-titled album remains an OG example of why the Grammys will never really be the institution it claims itself to be. Morning Phase is a good folk album from one of music’s great chameleons, but it’s no Beyoncé.
42. Natalie Cole: Unforgettable… with Love (1992)
Should’ve Won: R.E.M., Out of Time
I love Natalie Cole and I love Unforgettable… with Love, a moving tribute to her father Nat King. And I think, at the end of the day, her winning in 1992 was the right choice—even if it was a bit of a sentimental pick. Had I been around back then, I’m sure I would have wanted to see R.E.M. take it home for Out of Time—but the Grammys love getting mushy gushy like this.
41. Whitney Houston: The Bodyguard Original Soundtrack Album (1994)
Should’ve Won: R.E.M., Automatic for the People
This is where I drop the act about my disdain for soundtracks winning Album of the Year. Whitney Houston’s The Bodyguard Original Soundtrack Album earned its victory, especially because it features her rendition of Dolly Parton’s “I Will Always Love You”—which is, simply put, one of the most important songs of all time. But—and there’s always a but—R.E.M. should have won for Automatic for the People, one of the best alt-rock projects of the 1990s.
40. Blood, Sweat & Tears: Blood, Sweat & Tears (1970)
Should’ve Won: The Beatles, Abbey Road
Blood, Sweat & Tears made a great self-titled album. But—but—the Beatles should have won for Abbey Road. Need I say more?
39. John Lennon & Yoko Ono: Double Fantasy (1982)
Should’ve Won: Steey Dan, Gaucho
Awarded to John Lennon and Yoko Ono after Lennon’s passing in 1980, Double Fantasy was honored by the Grammys for Album of the Year even if it didn’t really deserve it. Sentimentality and grief paved the way, and it left albums by Kim Carnes, Quincy Jones, and Steely Dan in the dust. I would have given it to Steely Dan for Gaucho personally, which would have been a bolder and more compelling selection.
38. Phil Collins: No Jacket Required (1986)
Should’ve Won: Whitney Houston, Whitney Houston
“Sussudio” and “One More Night” are great tunes and No Jacket Required is a good album. But Whitney Houston and Dire Strait’s Brothers in Arms are great albums.
37. Various Artists: O Brother, Where Art Thou? Soundtrack (2002)
Should’ve Won: OutKast, Stankonia
For the most part, I really hate how many soundtracks are on this list (there are two exceptions, of course). The O Brother, Where Art Thou? soundtrack practically planted the seeds for the stomp clap explosion at the end of the 2000s/early 2010s, and we should forever bully it on principle. Two great records—Bob Dylan’s Love and Theft and OutKast’s Stankonia—got passed up in favor of movie songs, and I will always hold a grudge about that. Stankonia is one of the best rap albums of the 21st century, it should have walked away with Album of the Year unanimously.
36. Eric Clapton: Unplugged (1993)
Should’ve Won: U2, Achtung Baby
MTV Unplugged and soundtrack albums go hand-in-hand for me. I’m not a fan of most live records winning AOTY (see #57), and Eric Clapton’s Unplugged is no exception—especially because it won over U2’s brilliant Achtung Baby. Unplugged‘s reputation endures because of “Tears in Heaven,” which remains one of the most emotional songs in all of rock and roll. Out of 14 songs on the tracklist, only five were written by Clapton himself and he omitted performing most of his hits, save for “Layla.” Achtung Baby was the bigger musical achievement, and it should have been awarded for it.
35. Taylor Swift: Fearless (2010)
Should’ve Won: Lady Gaga, The Fame
Fearless isn’t one of Taylor Swift’s best albums, but the field of nominees in 2010 wasn’t all that strong, anyway. Her only competition was Beyoncé’s I Am…Sasha Fierce and Lady Gaga’s The Fame, of which wouldn’t have been bad picks. I’ll take Gaga.
34. Celine Dion: Falling into You (1997)
Should’ve Won: The Fugees, The Score
Before Celine Dion cemented herself as the “Queen of Power Ballads” with “My Heart Will Go On,” she racked up a few Grammys for her 1996 album Falling into You, including Album of the Year. It’s a pick that makes sense for the Recording Academy, but three of the other nominees—Beck’s Odelay, the Smashing Pumpkins’ Mellon Collie and the Infinite Sadness, and the Fugees’ The Score—have endured in the zeitgeist in far more inspired ways.
33. Bonnie Raitt: Nick of Time (1990)
Should’ve Won: Tom Petty, Full Moon Fever
Bonnie Raitt’s Nick of Time is a good album, but Fine Young Cannibals’ The Raw & the Cooked and Tom Petty’s Full Moon Fever are better—as is the Traveling Wilburys’ Vol. 1. I would have picked Full Moon Fever here, as it measured Petty’s brilliance without the Heartbreakers behind him. Nick of Time is a really fine example of a safe pick trumping all, but I can’t knock Raitt winning for one of her better mid-career albums.
32. Adele: 25 (2017)
Should’ve Won: Beyoncé, Lemonade
I love 25 and I love Adele, but in 2016 Lemonade was Beyoncé’s greatest achievement and one of the greatest albums of the last 20 years. Adele knew that too, as she cried on-stage while accepting the award and singing Beyoncé’s praises in the process. While it’s all fun and games watching two of the greatest performer’s of our time go head-to-head, it’s not so fun when the wrong one wins.
31. Bruno Mars: 24K Magic (2018)
Should’ve Won: Kendrick Lamar, DAMN.
When the 2018 Grammys happened, I remember pulling for Childish Gambino’s Awaken, My Love! to win. Six years later, and it’s clear that Kendrick should have snagged the win for DAMN.. Jay-Z was nominated for 4:44 and Lorde for Melodrama, but Kendrick’s best record would have been a certifiably based and just selection to make.
30. Various Artists: Saturday Night Fever Soundtrack (1979)
Should’ve Won: The Rolling Stones, Some Girls
The Saturday Night Fever soundtrack became one of the best-selling albums of all time, netting over 40 million copies moved across the globe. Even if it wasn’t a soundtrack, it’d still be one of the greatest disco records ever. Its win here was earned, though it’s not a better album than Jackson Browne’s Running on Empty or the Rolling Stones’ Some Girls. Personally, I would’ve gone with Some Girls but, knowing what direction the Grammys tend to go in, Running on Empty would have been a safe—and respectable—pick. But you can’t argue with sales.
29. Alanis Morissette: Jagged Little Pill (1996)
Should’ve Won: Mariah Carey, Daydream
I would have picked Mariah Carey’s Daydream here, but it was always a two-album race between that and Alanis Morissette’s Jagged Little Pill. The latter had commercial popularity and “You Oughta Know,” but Daydream had “Fantasy” and “Always Be My Baby.” It could’ve gone either way, but I wish Mariah would have taken it all the way.
28. Beyoncé: COWBOY CARTER (2025)
Should’ve Won: Charli XCX, Brat
Beyoncé went country and finally got her due in 2025, but it’s too bad it came on the heels of her weakest album in over a decade. Cowboy Carter is good, but it’s not Renaissance. Charli XCX’s Brat was a cultural phenomenon, one of the strongest trend-setting pop LPs that Academy’s ever nominated.
27. Glen Campbell: By the Time I Get to Phoenix (1969)
Should’ve Won: Simon & Garfunkel, Bookends
Glen Campbell winning in 1969 for By the Time I Get to Phoenix isn’t a bad move. I love this record and I love Glen, but him winning over Simon & Garfunkel and the Beatles is a head-scratcher. It could’ve been worse, though: Richard Harris could’ve won for A Tramp Shining.
26. Billy Joel: 52nd Street (1980)
Should’ve Won: Donna Summer, Bad Girls
Perhaps a consolation prize for not even getting nominated for The Stranger, the Recording Academy gave Billy Joel the prize for 52nd Street in 1980 and I’m fine with it, I guess. I would’ve given it to Supertramp for Breakfast in America or Donna Summer for Bad Girls. Hell, the Doobie Brothers could have gotten it for Minute by Minute and I wouldn’t have batted an eye. One of the few moments in Grammy history where each pick would have been justified. Oh, how I yearn for times like these.
25. Arcade Fire: The Suburbs (2011)
Should’ve Won: The Suburbs
An album that was great when it came out and hasn’t aged beautifully, The Suburbs beat a weak field of nominees. I probably would have preferred to see Katy Perry take it for her smash-hit Teenage Dream, but I’m not going to argue against Arcade Fire winning here. It was easily the best all-around LP out of the bunch, and the Grammys went with critical appeal over commercial this time around.
24. Paul Simon: Still Crazy After All These Years (1976)
Should’ve Won: Linda Ronstadt’s Heart Like a Wheel
Paul Simon’s Still Crazy After All These Years, Elton John’s Captain Fantastic and the Brown Dirt Cowboy, Linda Ronstadt’s Heart Like a Wheel, the Eagles’ One of These Nights—what a lineup. Any of these would have been great picks, but I’d have gone with Heart Like a Wheel here. Still Crazy After All These Years is one of Simon’s best, though.
23. Daft Punk: Random Access Memories (2014)
Should’ve Won: Random Access Memories
I think enough time has passed for the world to admit that Random Access Memories is a great record that deserved its Album of the Year win in 2014. Kendrick Lamar’s Good Kid, M.A.A.D City had a strong case, but this is an instance where the actual pick wasn’t too bad either. At least Macklemore and Ryan Lewis didn’t win for The Heist; them winning Best Rap Album over Kendrick was ridiculous enough already.
22. Adele: 21 (2012)
Should’ve Won: 21
Adele transformed into one of this century’s most important vocalists on 21, and her Album of the Year win was earned and deserved. Lady Gaga’s Born This Way and the Foo Fighters’ Wasting Light were solid runner-ups, but there was no doubt as to whether or not Adele was going to take home the brass.
21. Bad Bunny: DeBí TiRAR MáS FOToS (2026)
Should’ve Won: DeBí TiRAR MáS FOToS
It took almost 70 years for the Recording Academy to award a Spanish-language record its Album of the Year prize. Bad Bunny is one of the biggest superstars on the planet, and he earned every bit of his victory. The field had many worthy contenders, namely Lady Gaga’s Mayhem and Kendrick Lamar’s GNX, but Bad Bunny winning for a generationally good reggaeton album was the correct choice.
20. Bob Dylan: Time Out of Mind (1998)
Should’ve Won: Radionhead, OK Computer
Bob Dylan’s “comeback” moment winning Album of the Year was an easy choice, but it wasn’t necessarily the right one. The Grammys passed up on awarding Radiohead’s OK Computer—one of the greatest albums ever—the top prize and it’ll forever be a what-if. Time Out of Mind is great, but it didn’t effectively change the course of music over the last 25 years quite like OK Computer has.
19. Billie Eilish: When We Fall Asleep, Where Do We Go? (2020)
Should’ve Won: When We Fall Asleep, Where Do We Go?
Billie Eilish won five of the six Grammys she was nominated for in 2020, including Album of the Year for When We Fall Asleep, Where Do We Go? and Best New Artist. It became apparent immediately that Eilish was going to be among the best of her generation, and rewarding her so early in her career is a bright spot in an otherwise uninteresting 21st century for the Recording Academy. Eilish went up against longtime successes like Vampire Weekend, Bon Iver, H.E.R., and Lana Del Rey and beat them all, and she’s continued to wrack up awards at every corner since. Billie Eilish was shot out of a cannon and stuck the landing like no one else has.
18. Stan Getz & João Gilberto: Getz/Gilberto (1965)
Should’ve Won: Getz/Gilberto
Getz/Gilberto is the best jazz album to ever win this award. You can’t go wrong with top-shelf American-Brazilian bossa nova fusion. The field wasn’t strong, but Getz/Gilberto is incredible.
17. Taylor Swift: 1989 (2016)
Should’ve Won: Kendrick Lamar, To Pimp a Butterfly
It’s not Taylor Swift’s fault that she won Album of the Year in 2016. Blame the Recording Academy for executing one of the all-time biggest snubs in the history of the Grammys. Kendrick Lamar’s To Pimp a Butterfly was not just the best album put out in 2015, it’s one of the greatest rap albums of this century and before. But, 2016 was such a stacked year of nominees, too—Alabama Shakes, Chris Stapleton, The Weeknd. It’s likely the best field of nominees since 1985, and it’s fascinating how Swift put out—you could argue—the second, third or, even, fourth-best album of the bunch.
16. Paul Simon: Graceland (1987)
Should’ve Won: Janet Jackson, Control
I revisit Graceland often, but I revisit Control even more. This is the only time Janet Jackson has ever been nominated for Album of the Year and, in a fair and just world, she wins it, too.
15.Kacey Musgraves: Golden Hour (2019)
Should’ve Won: Janelle Monáe, Dirty Computer
One of the greatest country albums of the 21st century winning Album of the Year just feels good. I’m glad that it happened, and I’m glad it happened to Kacey Musgraves—whose LP Golden Hour was so brilliant that it turned her into the matriarch of the genre overnight. But Dirty Computer was also right there. That’s one of the best albums I’ve ever heard.
14. George Michael: Faith (1989)
Should’ve Won: Faith
Yes, Tracy Chapman was also nominated this year. And, while “Fast Car” and “Talkin’ ‘bout a Revolution” are two of the greatest songs ever written, George Michael’s Faith is the better all-around album. Faith stayed in the Top 10 on the Billboard 200 for 51 non-consecutive weeks, and it featured four #1 singles. Commercially and critically, it is one of the best pop albums of its era—and it cemented Michael, once and for all, as one of the greatest performers and entertainers of his generation.
13. Taylor Swift: folklore (2021)
Should’ve Won: folklore
2021 featured one of the Grammys all-time weakest Album of the Year nomination fields, and it was a two-album race the whole way. While Taylor Swift winning for folklore was a smart and valid choice, I would have been thrilled if Dua Lipa won for Future Nostalgia—one of the best pop albums of the last decade. But foklore, that’s Taylor at her best.
12. OutKast: Speakerboxxx/The Love Below (2004)
Should’ve Won: Speakerboxxx/The Love Below
The only album that I would’ve second-guessed not winning this year was the White Stripes’ Elephant, but OutKast’s Speakerboxxx/The Love Below earned this award and there’s no ifs, ands, or buts about it. The Atlanta hip-hop titans struck gold and delivered a commercial masterpiece, and the Grammys didn’t whiff on recognizing such a monumental success.
11. U2: The Joshua Tree (1988)
Should’ve Won: Prince, Sign o’ the Times
I think The Joshua Tree would probably rank higher if it didn’t beat out Sign o’ the Times, which is one of the greatest albums ever made, for Album of the Year. That’s just the way the chips fell though. U2 rock but Prince rules, and the Grammys snubbed him once for Purple Rain and elected to do so again three years later.
10. Judy Garland: Judy at Carnegie Hall (1962)
Should’ve Won: Judy at Carnegie Hall
1962 boasted the strongest field out of the first decade of ceremonies, with Judy Garland, Henry Mancini, Nat King Cole, and Ray Charles duking it out for Album of the Year. Garland ended up taking the whole thing for her live double-LP at Carnegie Hall, and I think the Academy got it totally right. Garland’s performance of “Over the Rainbow” here confirms it.
9. Stevie Wonder: Fulfillingness’ First Finale (1975)
Should’ve Won: Joni Mitchell, Court and Spark
1975 was a terrific year for the Grammys, and they had three top-tier records to choose from for Album of the Year: Stevie Wonder’s Fulfillingness’ First Finale, Paul McCartney and Wings’ Band on the Run, and Joni Mitchell’s Court and Spark. Any of these would have made sense, and Stevie is a tremendous pick, but I would have leaned towards Court and Spark. It’s one of Joni’s strongest records, and it would have been a prime opportunity for the Recording Academy to recognize her as one of the greats.
8. Simon & Garfunkel: Bridge Over Troubled Water (1971)
Should’ve Won: Bridge Over Troubled Water
The field of nominees in 1971 was interesting, largely because it featured a stacked lineup of artists—Simon & Garfunkel, Chicago, Carpenters, Elton John, James Taylor, and Crosby, Stills, Nash & Young. Crazily enough, only two of those acts were nominated for the best album of their careers, and Simon & Garfunkel ended up taking home the brass for Bridge Over Troubled Water over CSNY’s Déjà Vu. It’s a win that was earned, as Bridge Over Troubled Water was a brilliant coda to the duo’s career together. Likewise, it’s one of the greatest folk-rock albums of all time.
7. Stevie Wonder: Innervisions (1974)
Should’ve Won: Innervisions
The greatness of Innervisions would have trumped whatever field it was put into, but 1974 was an especially weak year of nominees. It was Innervisions and everything else. The next-closest pick would have been Roberta Flack’s Killing Me Softly With His Song, but the Grammys got it right this time, no matter how impossible it was for them to screw it up.
6. Michael Jackson: Thriller (1984)
Should’ve Won: Thriller
Michael Jackson won eight Grammys in 1984, including Album of the Year for Thriller. I don’t think there was ever a shred of doubt that MJ was going to walk away with the top prize, though the Police’s Synchronicity and David Bowie’s Let’s Dance were both good records. Thriller, however, is one of the best-selling albums ever and songs like “Billie Jean,” “Beat It,” and the title track are immortal for a reason.
5. Fleetwood Mac: Rumours (1978)
Should’ve Won: Rumours
Had I been alive in 1978 and was forced to choose between Rumours, Aja, and Hotel California, I would have simply combusted. Three of the sharpest rock records of the 1970s stacked against each other on music’s biggest night—what could go wrong? Rumours winning was an easy pick, and I’m not sure either of the other four nominees had much of a chance to begin with. Fleetwood Mac would never snag an Album of the Year nod again, but they scored when it mattered most.
4. Lauryn Hill: The Miseducation of Lauryn Hill (1999)
Should’ve Won: The Miseducation of Lauryn Hill
All hail Ms. Lauryn Hill, whose Album of the Year victory in 1999 for The Miseducation of Lauryn Hill only further cements the record as one of the greatest of all time. And looking at her competition—Madonna, Shania Twain, Sheryl Crow, and Garbage—it speaks volumes that the Grammys got it right and awarded her the top prize. To only drop one album in your career and have it win big on music’s biggest night and carry on as legendary far beyond that? It could have only been done by Ms. Hill.
3. Carole King: Tapestry (1972)
Should’ve Won: Tapestry
If you think George Harrison should’ve won Album of the Year in 1972 for All Things Must Pass, I won’t argue with that. It’s a brilliant record that separated Harrison from the shadow of the Beatles. But, Carole King’s Tapestry is also brilliant. Take your pick.
2. The Beatles: Sgt. Pepper’s Lonely Heart’s Club Band (1968)
Should’ve Won: Sgt. Pepper’s Lonely Heart’s Club Band
No album gets considered the greatest of all time more than Sgt. Pepper’s Lonely Hearts Club Band. Considering that, it’s miraculous that the Grammys gave it Album of the Year in 1968. They almost never award timelessness so highly. But, considering that the next best nominee was Bobbie Gentry, I guess it’s not so surprising after all. When you look at all 68 Grammy winners on this list, you can’t argue against the Beatles and you certainly can’t argue against Sgt. Pepper’s.
1. Stevie Wonder: Songs in the Key of Life (1977)
Should’ve Won: Songs in the Key of Life
For as bad as the Grammys can be and often are, the fact that they did award five of the greatest albums of all time their most-coveted prize is a refreshing relief. Songs in the Key of Life, the best double-album ever, beat out Georgie Benson, Chicago, Peter Frampton, and Boz Scaggs—which, on paper, isn’t the toughest lineup to overcome, sure. But Stevie Wonder’s magnum opus endures as such. Its existence is marvelous, and its placement at the top of this list is non-negotiable.
