Buddy Holly

He inspired generations of musical nerds from Elvis Costello to Kanye, not to mention most of the current-day NBA. You know you've arrived when Weezer writes a song about you.

Ray Charles

How is it that blind dudes always rock the freshest shades? Honorable blind guy mentions: Stevie Wonder, George Shearing and Ronnie Milsap.

Roy Orbison

Oh, snap, we picked Roy Orbison over Elton John! That's because Elton John's glasses are often not cool, while Orbison's



John Lennon

OK, we still kind of hate the round lenses, but the dude certainly had a look. Ringo, by the way, has terrible taste in spectacles.

Kool Moe Dee

Honorable hip-hop shout-outs should go to D.M.C, Heavy D, DJ Jazzy Jeff, and E-40 and company, but Kool Moe Dee had the best shades ever. And, yes, we just referred to the man as a "musical genius." Knowledge is king!