1. Bill Murray
Tiny camera and plaid suit? Sure, why not! Bill Murray is known as much for his hilarious roles as for his kooky behavior off-screen, like showing up at random parties uninvited and announced.
2. Brian Wilson
Most fear the beard, but what we fear the most is the mighty spandexedo the San Francisco Giants pitcher wore at the 2011 ESPYs.
3. Azealia Banks
Seemingly popping on the scene out of nowhere, the 21 year-old Harlem rapper/singer has definitely done it her way. Most of her awesome releases have been online exclusives she’s put out via her Tumblr.
4. Cee Lo Green
If anyone can make a decapitated red teddy bear look swaggy as a hat, it’s Cee Lo. The eccentric singer has worn many hats professionally and figuratively for twenty years now and shows no sign of slowing down.
5. Dolly Parton
Dolly was initially derided by her fellow country artists for her over-the-top appearance but after selling over 100 million records, there’s not denying she’s the Queen Of Country, big..erm…hair or not.
6. Will Ferrell
No other grown man will ever make donning a cheerleading uniform look more natural than Will Ferrell did during his Saturday Night Live days.
Her swan dress is still the butt of jokes, 12 years after the fact. It’s undeniable that her colorful wardrobe and beautiful videos have made as much of a mark on pop culture history as her music has.
8. Anthony Davis
Anyone who can rock a unibrow with such confidence deserves the admiration of us all.
10. Jack Black
Versatile, musical and hirsute: the Jack Black triple threat.
11. Karen O.
Before there was pantless Lady Gaga, there was the truly unique New Yorker Karen O., Yeah Yeah Yeah’s fashionable and fearless front-woman. No one can screech over a guitar riff quite like her.
12. Sascha Baron Cohen
Three words: neon green swimsuit.
14. Dennis Rodman
What other 6’6” tall Basketball Hall of Famer have you ever seen in a wedding dress just for the hell of it? Dennis Rodman truly set the standard for professional athlete antics during his reign in the 90s.
15. Gary Busey
The first line Gary Busey’s imdb bio says it all “A blond-haired, fair-complexioned actor with a toothy grin and capable of an unsettling glint in his eyes.” The unsettling glint is where the Busey magic happens, obviously.
16. Ron Artest
Feeling so confident in yourself and in the world that you change your name to Metta World Peace is nothing short of amazing.
17. Beth Ditto
Openly gay post-punk singer has been an inspiration for hundreds of young women with body issues because of her unabashed confidence - she even penned a column on body image for the British paper The Guardian. She’s also become a beloved fixture of the fashion and cosmetics world, recently coming out with her own signature line with the a major makeup brand.
18. Nicolas Cage
Nicolas Cage does what he wants! Even if that means staring in every single movie possible, no matter how questionable the outcome might be. Time to get excited for recently-announced National Treasure 3.
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