Top 10 Biggest Grammy Upsets

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Every year, the music industry gets together to award the most talented musicians of the previous year with a golden gramophone. With all the competition, crowd favorites don't always walk away with the prize. However, there are certain times where a clear winner is shunned and you're left wondering "What were they thinking"? Today we take a look at the 10 biggest upsets in Grammy history.

10Rick Springfield beat Bruce Springsteen - 1981

Perhaps someone at the Academy was suffering from dyslexia or maybe someone didn't take their crazy pills in the morning but either way, Best Vocals were handed out to Jessie's Girl instead of powerful The River in 1981.

9Will Smith beats Notorious B.I.G - 1998

Yeah that's right, I went there. The Academy went for the popular choice instead of the best one in 1998. Men In Black ousting B.I.G's Hypnotize? or even Missy Elliot's The Rain? Sorry but no.

8Baha Men - Who Let the Dogs Out - 2001

Baha Men's Who Let The Dogs Out is the obnoxious equivalent of Black Eyed Peas teaming up with Ke$ha. Horrible.

7Steely Dan Defeat Radiohead - 2001

Steely Dan, a band that hadn't been relevant since the 70s, took home a gramophone by beating Radiohead's masterpiece, Kid A. Radiohead did win best alternative album during the same event as a consolation prize.

6Tony Bennett wins Best Album for "MTV Unplugged" - 1995

Wait wait, don't close your browser, hear me out. There's nothing wrong with Tony Bennett's Unplugged album, but there was nothing original about it either. Here are 5 albums we would have put above Mr Bennett in 1995.

  • Oasis - Definitely Maybe
  • Nine Inch Nails - Downward Spiral
  • Soundgarden - Superunknown
  • Pulp Fiction Soundtrack
  • Pearl Jam - Versus

And that doesn't include amazing efforts by Hole, Nas, Pavement, R.E.M and more. *sigh*

5Milli Vanilli won - 1989

Did you hear me? Milli Vanilli won. I don't even care who they were up against, it could have been the creepy janitor who whistles when he cleans the toilet in the office and it still would have been an upset.