The 17 Most Unexpected Grammy Winners
1. Barack Obama
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.
2. Tia Carrere
The Wayne’s World dreamgirl is a two-time winner for Best Hawaiian Music Album.
3. Baha Men
Let me give you a second to process that. Yes, “Who Let the Dogs Out” was officially honored by the Recording Academy for its excellence.
4. Orson Welles
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.
5. “Weird Al” Yankovic
Another three-time Grammy winner, although his work is just a little bit different than that of Welles.
6. Zach Braff
Braff won for compiling the Garden State soundtrack (which you have to admit totally ruled, no matter your opinion about the actual movie).
7. Young MC
Come on, you know “Bust a Move” deserves a Grammy just as well as you know every verse of the song.
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
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.
10. Al Franken
The only person to ever win a Spoken Word Recording Grammy for slamming Rush Limbaugh.
Two Grammys, somehow. ???
12. Billary Clinton (both of ‘em)
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.
13. Mikhail Gorbachev
Like, what? WHAT?
14. Sophia Loren
Of course this queen of the universe has a Grammy along with all her other achievements.
15. Richard Pryor
He earned FIVE Grammys for his legendary comedy albums, way ahead of a huge number of famous musicians. Whoa!
16. Kate Winslet
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.
17. And, of course, Elmo
Who wins everything, always, including all of our hearts.