Daniel Tosh
The prince of controversial comedy, Daniel Tosh. He created a TV show Tosh.0 with the intent to be as deliberately offensive and crude as possible, without getting kicked off the air. Honestly, maybe that was always the goal— to continue reaching that line. He was also a part of the animated series Brickleberry as Malloy, a really inappropriate bear. The entire show was inappropriate, really, but it tackled some tough topics. So, that evens out.