Every Album of the Year Grammy Winner Ranked From Worst to Best

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 week, they awarded Swift for her 2022 LP Midnights, so we thought it would be apt to take a look at all 66 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.

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66. 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 in critical categories. In 1963, though, comedian Vaughn Meader winning over Ray Charles might go down as one of the biggest misfires in Grammy history.

65. 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.

64. 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 legend of the composer craft, 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.

63. 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 won over Revolver, one of the greatest records ever made.

62. 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.

61. 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 the third-winningest Grammy Award nominee 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.

60. 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.

59. 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.

58. Norah Jones: Come Away with Me (2003)

Should’ve Won: Bruce Springsteen, The Rising

The chokehold Norah Jones had on department store radio stations in the mid-2000s ought to be studied 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, especially, Bruce Springsteen’s career-revitalizing LP The Rising is a head-scratcher.

57. 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 far-and-away smarter picks for Album of the Year. But, at the end of the day, channel ORANGE deserved this award.

56. 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?

55. 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.

54. Stan Getz & João Gilberto: Getz/Gilberto (1965)

Should’ve Won: Barbra Streisand, People

The best jazz album to win this award, Getz/Gilberto was a fine choice in 1965. I probably would have picked Barbra Streisand’s People instead, but you can’t go wrong with one of the best American-Brazilian bossa nova fusion records of all time.

53. 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 and pop-rock albums of its era. The Fab Four would get their kudos two years later, and I’d argue that they should have won all five of the Album of the Year nominations they got between 1966 and 1970.

52. 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 likely one of 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 it to Justin Timberlake for FutureSex/LoveSounds, one of the best pop records of the entire 21st century.

51. 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 latest 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.

50. Toto: IV (1983)

Should’ve Won: Donald Fagen, The Nightfly

One of the weaker nominations 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.

49. 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.

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 it could ever be. It’s a tight race between Joel and Floyd, but I’ll give it to Joel—Glass Houses is great, maybe Joel’s very best album that isn’t The Stranger.

47. 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.

46. U2: How to Dismantle an Atomic Bomb (2006)

Should’ve Won: Kanye West, Late Registration

Not an entirely compelling slate of nominees, but the Recording Academy missed out on giving Kanye a trophy for Late Registration. The chokehold U2 has on the music industry ought to be studied for decades to come. How to Dismantle an Atomic Bomb was good but it wasn’t Album of the Year good, you know?

45. 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 further. 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 particularly close.

44. 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, especially, 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 had a certain unshakable momentum and was awarded for it.

43. 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 it. Stankonia is one of the best rap albums of the 21st century, it should have walked away with Album of the Year unanimously.

42. 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 we’re tired.

41. Judy Garland: Judy at Carnegie Hall (1962)

Should’ve Won: Ray Charles, Genius + Soul = Jazz

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, but I would’ve given it to Charles for another brilliant performance on Genius + Soul = Jazz—which featured a 29-year-old Quincy Jones leading the big band arrangements with Ralph Burns. The Breakfast at Tiffany’s soundtrack would have been a good pick, too, if only for “Moon River” alone.

40. 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 good 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.

39. 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.

38. 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.

37. Bruno Mars: 24K Magic (2018)

Should’ve Won: Jay-Z, 4:44

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 Jay-Z should have snagged the win for 4:44. Kendrick Lamar was nominated for DAMN. and Lorde for Melodrama, but Jay-Z’s victory lap record would have been a certifiably based and just selection to make.

36. 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?

35. 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.

34. 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.

33. 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 are career-best performances, too. Steely Dan are all-time greats, and the Recording Academy were making up for passing over Aja and Gaucho during their respective years nominated.

32. Eric Clapton: Unplugged (1993)

Should’ve Won: U2, Achtung Baby

MTV Unplugged and soundtrack albums go hand-in-hand for me. I’m not so much a fan of live records (see #44), 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 ‘n’ 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 as such.

31. Taylor Swift: Fearless (2010)

Should’ve Won: Beyoncé, I Am…Sasha Fierce

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 Beyoncé should have won. Lady Gaga’s The Fame wouldn’t have been a bad pick, either.

30. 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 albums.

29. Adele: 25 (2017)

Should’ve Won: Beyoncé, Lemonade

I love 25 and I love Adele, but Lemonade is 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.

28. 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.

27. Various Artists: Saturday Night Fever Soundtrack (1979)

Should’ve Won: Jackson Browne, Running on Empty

The Saturday Night Fever soundtrack became one of the best-selling albums of all time, netting over 40 million copies sold 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 should have been a safe—and respectable—pick. But you can’t argue with sales.

26. 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.

25. Celine Dion: Falling into You (1997)

Should’ve Won: The Smashing Pumpkins, Mellon Collie and the Infinite Sadness

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 greater ways.

24. 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 is the most 21st century move the Grammys could have made 30 years beforehand. They were ahead of their time, I guess. Nonetheless, I love this record and I love Glen, but him winning over Simon & Garfunkel and the Beatles is just… puzzling. It could’ve been worse, though—Richard Harris could’ve won for A Tramp Shining.

23. 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, even more so, Donna Summer for Bad Girls. Hell, the Doobie Brothers could have gotten it for Minute by Minute and I wouldn’t have even second-guessed it. One of the few moments in Grammy history where each pick is a safe and inarguable one. Oh, how I yearn for times like these.

22. Daft Punk: Random Access Memories (2014)

Should’ve Won: Kendrick Lamar, Good Kid, M.A.A.D City

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 should have won for Good Kid, M.A.A.D City, but this is an instance where the actual pick wasn’t too bad, either. At least Macklemore & Ryan Lewis didn’t win for The Heist; them winning Best Rap Album over Kendrick was sacrilegious enough already.

21. Taylor Swift: Folklore (2021)

Should’ve Won: Dua Lipa, Future Nostalgia

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’d have liked to see it go to Dua Lipa for Future Nostalgia—one of the best pop albums of the last decade.

20. Paul Simon: Still Crazy After All These Years (1976)

Should’ve Won: Elton John, Captain Fantastic and the Brown Dirt Cowboy

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 Captain Fantastic here. Still Crazy After All These Years is one of Simon’s best, though.

19. 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, and I’m glad Morissette got her props.

18. 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 real doubt as to whether or not Adele was going to take home the brass.

17. 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.

16. 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 taking home 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 a torchbearer for her generation, and her massive successes so early in her career is one of the brightest spots in an otherwise uninteresting 21st century for the Recording Academy. She 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.

15. 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.

14. 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.

13. 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.

12. 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 album all-around. 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.

11. Kacey Musgraves: Golden Hour (2019)

Should’ve Won: Golden Hour

The greatest country album 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 a surprise stroke of brilliance that turned her into the matriarch of the genre overnight. And, in a category filled out by Janelle Monáe, H.E.R. and Cardi B, the record’s greatness feels even more massive and Musgraves’ victory feels even more hard-earned.

10. 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 masterpiece, and the Grammys didn’t whiff on recognizing such a monumental success.

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 here. It’s one of Joni’s greatest records, and it would have been a prime opportunity for the Recording Academy to pay her the due she didn’t really get until 2024.

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 lumped into, but 1974 was a weak year of nominees anyways. It was, truly, 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 it, 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. 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 such brilliance. To only drop one album in your career and have it win the top prize at music’s biggest night and endure as immortal far beyond that, it could have only been done by Ms. Hill.

4. 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, so is Carole King’s Tapestry, which is—top to bottom—a perfect, immortal, timeless LP.

3. 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.

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. Considering that the next best nominee was Bobbie Gentry, I guess it’s not so surprising after all. But, when you look at all 66 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 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, 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.