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Metallica's ...And Justice For All loses to Jethro Tull's Crest of a Knave for Best Hard Rock/Metal (1989)
The Holy Grail of perhaps all award-show upsets. Heavy music had gotten short shrift from the Grammy folks since its inception, so the introduction of the Best Hard Rock/Metal category in 1989 was supposed to be the long-awaited mainstream coronation of Metallica (who were nominated for ...And Justice For All and who were also booked to perform). The prize went to Jethro Tull, who received boos upon the announcement and were confused they were even nominated in the first place.
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Eminem's The Marshall Mathers LP and Radiohead's Kid A both lose to Steely Dan's Two Against Nature for Album of the Year (2001)
In 2001, the two front-runners for Album of the Year were Radiohead and Eminem. Each were nominated for huge watershed releases: The former had released the moody, complicated Kid A, the latter the caustic, bipolar The Marshall Mathers LP. They each represented high points for two of the 21st centuries greatest artists, and yet Steely Dan won for their comeback album Two Against Nature in yet another case of the Grammys looking back when they should have been looking forward.
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Amy Winehouse's Back to Black loses to Herbie Hancock's River: The Joni Letters for Album of the Year (2008)
While Amy Winehouse's sound wasn't necessarily progressive, it was refreshing, and her second album Back to Black was a huge cultural milestone that scored both critical and commercial success. In a notoriously head-scratching upset, Herbie Hancock's collection of jazz interpretations of Joni Mitchell songs (which most people were not aware of until it was nominated) walked away with the win.
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Justin Bieber loses to Esperanza Spalding for Best New Artist (2011)
Bieber was the biggest thing to happen to music in years when his My World albums became massive hits. Though he sold millions of albums and was the most identifiable and successful teen idol since the boy band era, Bieber lost to a jazz bassist.
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Elvis Costello loses to A Taste of Honey for Best New Artist (1979)
The Best New Artist category is a weird one, because the rules govern that ''new'' means ''we've never heard of you before,'' which is why artists with five albums have been nominated for the award. The winners list is full of never-were's, including A Taste of Honey, who bested post-punk legend Elvis Costello in '79 and were never heard from again.
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U2's All That You Can't Leave Behind loses to the O Brother Where Art Thou soundtrack for Album of the Year (2001)
After floundering for nearly a decade in the wake of Zooropa and Pop, U2 got back to the business of being U2 for the turn-of-the-century statement All That You Can't Leave Behind. It became an iconic album with a handful of hits, and ushered in U2's third act as a legendary band. But it apparently was not as powerful as the collection of bluegrass tunes that made up the soundtrack to the overrated Coen Brothers flick O Brother Where Art Thou?
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Metallica's ''Enter Sandman'' loses to Sting's ''The Soul Cages'' for Best Rock Song (1992)
Metallica just can't buy a break. Three years after getting upset by Jethro Tull, the band's juggernaut crossover anthem ''Enter Sandman'' lost the contest for Best Rock Song to a nondescript Sting vibe-a-thon. Don't weep for them, though: They won Best Metal Performance that same year, and have collected 8 prizes over the course of their long career (though they still come up short when it comes to Sting, who has 11 on his own plus 6 more with the Police).
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Notorious B.I.G.'s ''Hypnotize'' and Missy Elliott's ''The Rain (Supa Dupa Fly)'' both lose to Will Smith's ''Men in Black'' for Best Rap (1998)
Look, Will Smith is great, and we won't begrudge him his victory the following year for ''Getting' Jiggy Wit It,'' even though it beat out Lauryn Hill's ''Lost Ones'' and Jay-Z's ''Hard Knock Life (Ghetto Anthem).'' But the success of ''Men in Black'' in '98 was pretty jaw-dropping, especially considering the sentiment surrounding the Notorious B.I.G. (who was murdered right as ''Hypnotize'' was peaking) and the game-changing weirdness of Missy Elliott's debut single.
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Madonna's ''Music'' and Britney Spears' ''Oops!...I Did It Again'' both lose to Macy Gray's ''I Try'' for Best Female Pop (2001)
Madonna was in the midst of yet another career surge when she dropped ''Music,'' a song so durable it made an appearance at her recent Super Bowl halftime show. Spears' ''Oops...I Did It Again'' was one of the year's biggest songs and proof that she was going to have a long-lasting career. Gray's ''I Try'' remains a pretty song, but she has not had nearly the longevity and timelessness of the two women she beat.
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Bruce Springsteen's ''Born in the USA'' loses to USA for Africa's ''We Are the World'' for Record of the Year (1986)
It's hard to root against a charity single, but for all of USA for Africa's star power and good intentions, the big secret is that the song is terrible. What's more, Springsteen's ''Born in the U.S.A.'' was a rare bird, a shout-along anthem that painted a dystopian picture of life in Reagan's America. ''We Are the World'' was a nice charity stunt, but ''Born in the U.S.A.'' was the superior record.
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Mariah Carey's ''Vision of Love'' and Sinead O'Connor's ''Nothing Compares 2 U'' loses to Bette Midler's ''From a Distance'' for Song of the Year (1991)
There's nothing wrong with Bette, but Carey's ''Vision of Love'' introduced a new era of R&B that ruled the radio in the '90s, and even if you're looking for naked sentiment, O'Connor's take on Prince's ''Nothing Compares 2 U'' is the superior piece of treacle.
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No Doubt's ''Don't Speak'' loses to Shawn Colvin's ''Sunny Came Home'' for Song of the Year (1998)
Like some of the other awards on this list, it certainly seemed like a good idea at the time. But in retrospect, it seems crazy that one of the definitive tunes of the late '90s (and Gwen Stefani's breakout moment) lost a Grammy contest to a piece of Dawson's Creek strum-and-feel-bad campfire rock.
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Red Hot Chili Peppers' ''Californication'' loses to Creed's ''With Arms Wide Open'' for Best Rock Song (2001)
Don't weep for the Peppers, who have won a total of seven Grammys over the course of their career. But ''Californication,'' the band's greatest latter-day statement of purpose, should have bested ''With Arms Wide Open,'' a song about which the best thing you can say is that it's one of the least obnoxious Creed tracks.