When I was first lent a Doug Stanhope CD, he was described to me as a comic with "good bar stories." It's no wonder: his delivery style is profane and crude, and he loves questioning societal conventions from the ground up. Many of his filthy and hilarious stories are from his time traveling out on the road. I was able to see him, inebriated and shaggy-haired, at a packed dive bar in Ocean Beach a few years back and his rants absolutely slayed. If you like blue comedy, he's one of the best out there.
For the caricature, I decided to make him a sunburnt, annoyed hitchhiker alone on an Arizona highway, complete with a cigarette and a beer, and wearing the "Libertarian" baseball jersey he wore for a special he put on in New York when he ran for president in 2008.
Here he is delivering the famous "Aristocrats" joke for Penn Jilette and Paul Provenza's movie (NSFW!):
As a guest on the excellent Charlie Brooker's "Screenwipe":