1. Kate Winslet
When you look at soon-to-be space cadet Kate Winslet’s impressive award-ography — Grammy winner for “Best Spoken Word Album for Children” in 2000, Academy Award winner for The Reader in 2008 — only one thing comes to mind: poor Leonardo DiCaprio.
2. Stephen Colbert
Satirist and eagle-eyed newsman Stephen Colbert holds the strange honor of being the only comedian to win the Grammy for “Best Comedy Album” with a Christmas album. Assuming fellow Grammy honoree Louis CK doesn’t drop his long-belated Christmas carol cover album next year, natch.
3. Barack Obama
Commander In Chief? Try Commander In Chief And Also Grammy Winner Because Lets Get Our Priorities Straight Here. Barack Obama swept the “Best Spoken Word” category in 2008 with the audio book version of “The Audacity of Hope,” joining Jimmy Carter and Bill Clinton among the Presidential Grammy Winner elite.
4. Young MC
It’s a shame that more people aren’t aware how the man that first taught us to bust a move also took home the Grammy for the fledgling “Best Rap Performance” category, the second of such awards ever given out. It’s almost enough to make you forget about his stint on Celebrity Fit Club. Almost.
Think what you will of Sesame Street’s premiere little monster, but “Multi-Grammy Winning Vocalist” probably isn’t the first thing that pops into your brain. The folks behind the fuzzy red muppet have waddled home with not one, but three Grammys — in 1999, 2000, and 2002 — all for “Best Musical Album for Children.”
6. The Baha Men
A nation rejoiced when Trinidadian reggae trio The Baha Men swept the 2001 Grammy category for “Best Song Pertaining To Dogs And The Act Of Letting Them Out.” No, just playing — they won for “Best Dance Recording,” narrowly beating out Eiffel 65, Moby, and Enrique Iglesias. In other news: hey, remember Eiffel 65?
7. R. Kelly
Okay, wait, wait, wait. Now, we don’t think it’s unbelievable that R. “The Pied Piper of R&B” Kelly won a trio of Grammys. (If we had it our way, he’d win a Lifetime Achievement award every single year for “Ignition (Remix)”) What we find unbelievable is that the only song he’s ever won a Grammy for is “I Believe I Can Fly,” of Space Jam fame. Argument #1,599,000 that Space Jam is mankind’s greatest achievement since electricity.
8. Mikhail Gorbachev
So, here’s a sentence you probably didn’t think you’d read today: what do Kate Winslet and former Soviet Union General Secretary Mikhail Gorbachev have in common? They both have Grammy awards for “Best Spoken Word Album for Children” displayed proudly on their mantles. Gorbachev won the award along with Bill Clinton and Sophia Loren for their interpetation of classic children’s story “Peter and the Wolf.”
9. Martin Scorsese
Good Guy Grammys: gives Martin Scorsese one of the biggest winnable entertainment awards a full month before the Academy finally got around to tossing him a “Best Director” statuette. Marty took home a golden gramophone for directing the Bob Dylan documentary No Way Home, earning him a “Best Long Form Music Video” award.
10. Tia Carrere
You could say that Tia Carrere won her three Grammy awards because she’s a talented musician with the voice of an angel, perfectly capable of capturing what makes Hawaii’s islands such an amazing habitat. Or you could say that her wildly successful musical career is just life imitating art after she signed that contract at the end of Wayne’s World. We’ll take either/or.