10. Willie Nelson
While he may have gotten recent attention for being the only person able to outsmoke Snoop Lion, Willie Nelson is also a dude with some serious rebel style that fits perfectly with his anti-establishment attitude and music. W
illie was one of the founders of outlaw country, a sub-genre of country music that was mostly a big "fuck you" to the corniness that the music industry Nashville had become by the late 1960s. With his signature headband, long red hair, and proud drug usage, his whole manner of being and style was one big flipping off of the industry and The Man.