2. Bob Dylan
Bob Dylan was a rebel before anybody even knew his name. Prior to the release of his first album, he told Columbia's press people that he was a runaway who spent his childhood working at a traveling carnival. He wrote the greatest protest songs ever created, but then quickly moved away from them near the height of the Civil Rights Movement. He plugged in at the 1965 Newport Folk Festival and spend the next year playing incredibly loud rock & roll shows to crowds full of booing folkies. He made a country album at the peak of the psychedelic era, and 10 years after that, made a gospel album and went on a tour featuring just that material. In recent years, he appeared in commercials for Victoria's Secret and the Cadillac Escalade. Simply put, he doesn't give a fuck and he never does what anyone expects.