Top 10 Grammy Upsets

The Academy of Recording Arts may have seen these coming, but we certainly didn't. For this list, we’re defining a Grammy upset as one in which an artist was expected to win a specific award in a given year but surprisingly lost to another artist. We’re excluding lifetime snubs where a given artist was overlooked for a specific category or altogether for their entire careers. Look for those in our Top 10 Grammy Snubs video. Join WatchMojo.com as we count down our picks for the top 10 Grammy Upsets. Special thanks to our users Marcomarco and Jerome Magajes for submitting the idea on our Suggest Page at WatchMojo.comsuggest
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The Academy of Recording Arts may have seen these coming, but we certainly didn't. Welcome to WatchMojo.com and today we’re counting down our picks for the top 10 Grammy Upsets.

For this list, we’re defining a Grammy upset as one in which an artist was expected to win a specific award in a given year but surprisingly lost to another artist. We’re excluding lifetime snubs where a given artist was overlooked for a specific category or altogether for their entire careers. Look for those in our Top 10 Grammy Snubs video.

#10: Herbie Hancock Over Amy Winehouse, Kanye West
50th Annual Grammy Awards (2008)


Hancock’s contribution to jazz and the creation of the post-bop sound can’t be denied. But when his Joni Mitchell tribute became the second jazz effort to win Album of the Year, even the musician himself was stunned. Industry watchers had tapped either Amy Winehouse or Kanye West, who were both having incredible years and were already Grammy winners that night.

#9: Eric Clapton Over Nirvana
35th Annual Grammy Awards (1993)


There’s no question “Layla” is an incredible track. But it was originally released in 1971 while the ‘90s was defined by grunge. And while Pearl Jam’s “Jeremy” was also passed over, it was the shunning of Nirvana’s adolescent anthem of indifference and one of alt-rock’s most iconic songs that really shocked us. To make matters worse, the reworked take of “Layla” that won Best Rock Song was an acoustic and decidedly un-rocking version.

#8: The Arcade Fire Over Lady Gaga
53rd Annual Grammy Awards (2011)


These Montreal rockers made Grammy history when The Suburbs nabbed Album of the Year. The win didn’t only make them the first indie act to get the prize but also had little monsters all over the web shocked and confused when Mother Monster didn’t take the cake. Lady Gaga had been making headlines and topping charts the world over so Arcade Fire’s win understandably left many people “speechless.”

#7: DJ Jazzy Jeff & the Fresh Prince Over Public Enemy
34th Annual Grammy Awards (1992)


Few rap acts were as critically acclaimed in the late ‘80s and early ‘90s as Public Enemy. With their politically inspired lyrics and groundbreaking hip-hop sound, they’d had their share of Grammy nominations. But when their album Apocalypse 91… The Enemy Strikes Black lost Best Rap Performance to DJ Jazzy Jeff and the Fresh Prince’s “Summertime,” everyone was flabbergasted; how did one mindless, nostalgic single top a full length, critically acclaimed top 10 album?!

#6: Baha Men Over Everyone Else
43rd Annual Grammy Awards (2001)


Who would’ve thought one of “Rugrats in Paris: The Movie”’s theme songs was better than tracks by Moby or Enrique Iglesias? But that seems to be what the Academy was saying when it gave Baha Men the Grammy for Best Dance Recording. “Who Let the Dogs Out?” may’ve reached the Billboard Hot 100’s top 40, but it’s also commonly cited as one of the worst songs ever. But apparently still better than Eiffel 65, who were also nominated that year.

#5: Steely Dan Over Radiohead, Eminem
43rd Annual Grammy Awards (2001)


For one of the night’s biggest categories, a jazz rock band that peaked in the ‘70s beat out critical darlings Radiohead and one of rap’s biggest stars Eminem for Album of the Year in 2001. Kid A and The Marshall Mathers LP may’ve been chart-toppers that were considered some of the finest works in the respective artist’s careers, but it was Steely Dan’s Two Against Nature that took the prize.

#4: A Taste of Honey Over Elvis Costello
21st Annual Grammy Awards (1979)


By combining folk, blues and reggae, and writing some of pop’s most clever and biting lyrics, Elvis Costello was slowly shaping the sound of punk rock and new wave. Also nominated for Best New Artist were the up-and-coming rockers The Cars. So, during a time when disco was quickly losing its cool, it seemed quite outrageous that the recording act which had topped the charts with “Boogie Oogie Oogie” took home the trophy in 1979.

#3: Christopher Cross Over Pink Floyd, etc.
23rd Annual Grammy Awards (1981)


When it comes to the Grammys, the early ‘80s were all about Christopher Cross. Why? The pop and soft rock artist somehow managed to win all four of the night’s biggest categories over more established and well-received names like Frank Sinatra, Barbra Streisand and Pink Floyd. “Sailing” may have been a number-one smash but it certainly didn’t have the lasting musical legacy that its fellow nominees later left.

#2: Jethro Tull Over Metallica
31st Annual Grammy Awards (1989)


In order to capitalize on the genre’s popularity, the Grammys recognized the year’s best hard rock and metal performance for the first time in 1989. But when prog rockers Jethro Tull won the trophy for Crest of Knave – beating out frontrunner Metallica in the process – metal fans and music critics were enraged. Not only did few people think the band was on par with the other nominees; many also felt they didn’t fit in hard rock OR metal.

Honorable Mentions


O Brother, Where Art Thou? Over U2, OutKast, and Bob Dylan for Album of the Year, 44th Annual Grammy Awards (2002)
Will Smith Over The Notorious B.I.G., Missy Elliott for Best Rap Solo Performance, 40th Annual Grammy Awards (1998)
Rick Springfield Over Bruce Springsteen for Best Rock Vocal Performance, 24th Annual Grammy Awards (1982)
Celine Dion Over The Fugees for Album of the Year, 39th Annual Grammy Awards (1997)

#1: The New Vaudeville Band Over The Beatles
9th Annual Grammy Awards (1967)


The Beatles had already lost to “Mary Poppins” for Best Original Score with “A Hard Day’s Night” in 1965. So when the world’s biggest band lost out AGAIN on Grammy recognition two years later for Best Contemporary Rock & Roll Recording to a POP song no less, many people cried foul. To top things off, The New Vaudeville Band’s “Winchester Cathedral” was even knocked off the number-one spot on the American charts by fellow category nominees, The Beach Boys.

Do you agree with our list? What do you think was the biggest Grammy upset? With new top 10s published every day, be sure to subscribe to WatchMojo.com.
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