Robert Crumb. Where to start? In his own words, he was born weird. So that is as good a place as any. He was and is a prolific artist and in the sixties became a favourite of the 'counterculture' with his cartoon images in comics and album covers etc. His most famous creations were Mr Natural and Fritz the Cat. But he was also a musician of sorts with a taste for old style 20s music. I would describe him as a radical traditionalist!
Below is a selection of his music and a wonderful cartoon of Mr Natural.