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The 17 Most Unexpected Grammy Winners

You don't need to be a musician to win a Grammy. Just ask Kate Winslet and Mikhail Gorbachev.

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1. Barack Obama

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The President was recognized in 2009 for the audio recording of his bestselling and widely acclaimed memoir, Dreams from My Father, back when he was just a lowly Grammy-winning Senator.

4. Orson Welles

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The writer/director/actor/overall genius won THREE Best Spoken Word Album Grammys for the soundtrack to Citizen Kane, a recording of Donovan's Brain, and "Great American Documents." There was nothing this man was bad at doing.


8. Shaggy

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He won Best Reggae Album for Boombastic in 1996, although I'm pretty sure he should have won for "It Wasn't Me," AKA the best song ever written about creepin' around on your signifcant other.


9. Whoopi Goldberg

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The famous EGOT-er won for Best Comedy Recording in 1985 for Whoopi Goldberg—Original Broadway Show Recording, and later appeared on 30 Rock to hilariously shove it in all of our faces.

12. Billary Clinton (both of 'em)

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Oh, you thought they couldn't be more of a power couple? Bill won by collaborating with the two following fellow weird Grammy winners on a reading of Peter and the Wolf, and Hillary for reading her book, It Takes a Village to Raise a Child.


16. Kate Winslet

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Oh, cool, Kate Winslet, you not only are a brilliant and beautiful actress, but also a Grammy-award winner for Best Spoken Word Album for Children. Casual human.