Top 10 Biggest Grammy Upsets

We take a look at the biggest failures in Grammy Awards history

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.


Rick 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.


Will 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.


Baha 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.


Steely 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.


Tony 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.

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


Milli 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.


Christopher Cross - 1980

Let's play a quick game, pick the musician least likely to win a Grammy from the following list:

Ok done? Good. Now give him the Grammy.


Mary Poppins beat The Beatles - 1964

In 1964, it was a battle between one acid trip and another. As memorable of a movie as Mary Poppins was (It's the one with the nanny and her umbrella right?), putting it over The Beatles' A Hard Day's Night is a travesty.


Nirvana and Pearl Jam lose to Eric Clapton - 1992

Alright, we have no beef with Clapton, but let's be serious for a second here; Layla over Smells Like Teen Spirit AND Jeremy? What kind of a sick joke is this? Smells like Academy Favoritism. Grunge got gipped.


Jethro Tull beats Metallica - 1989

Even during Jethro Tull's peak and Metallica's lowest, no one in their right mind would ever award the original JT a win over Metallica. In 1988 it was the case as And Justice For All lost out to Crest of the Knave. We're all for flute solos but come on! You know it's bad when your own record label tells you (Jethro) to not show up because you "weren't likely to win".

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Metallica Grammy Awards The Beatles Milli Vanilli Tony Bennett Radiohead Will Smith Nirvana Bruce Springsteen MTV Unplugged Top Lists

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