5. Iggy Pop
Long before Marilyn Manson, Ziggy Stardust and even Alice Cooper, there was Iggy Pop, the crazed alter-ego of James Newell Osterberg, Jr. Iggy had no problem cutting his chest open with glass, diving headfirst into crowds (only occasionally dislocating his shoulder in the process) and releasing album after album that didn't have a tiny chance of landing a song on the radio. He was playing punk 10 years before it was cool or even had a name, and partied so hard in the 1970s that he wound up in a mental asylum.
Sure, he appears in John Varvatos ads now and does private gigs for sunglass companies and Fashion Week, but he can make anything seem cool. Besides, he didn't earn any money back in the day and he deserves this now. Also, his music is so noncommercial that he even sang in French on his last solo album.