7. Doug Stanhope
The answer to the headline of a 2006 feature on this guy in British GQ, “Is This America’s Most Depraved Man?” depends on who you ask. When it comes to boundaries, it doesn’t seem like Doug Stanhope has many. Jokes about subjects like terrorism, misogyny, and suicide are completely fair game, and much of his stand-up tends to be about politically charged subjects in a fashion so offensive that, in 2004, a total of 600 people walked out of one of his gigs.
The thing about his stand-up, though, is that it’s also completely self-aware. It’s clear that he just wants to mess with people, and he plays upon their sensitivities well. Depraved or not, by doing so, he’s become one of the most notoriously controversial guys out there. And, of course, we all know the saying in Hollywood: Any press is good press.