I'm always surprised that people hold such a high opinion of Penn Jillette on O&A. He would just treat the show like it was his own podcast and barrel through with his own sermons and stories that gave zero chance for natural conversation.
Some other people I didn't care for on the show:
Joe Derosa: Tried way too hard to ingratiate himself into the Comedy Cellar mentality, which ended up blowing up in his face when he went after easy pickings like Skaterboi Quan and Dr. Steve. He was a dud on O&A, but I did think he was great on Uninformed.
Louis C.K: Just became this pretentious blowhard after his show went big and always acted like he was too big for the room. I mean, he was, but don't come onto the show, so we can listen to you "mmmhmm" in the background like some bored comedic adjudicator who just heard a joke that doesn't meet their bloated head standards.
Big A: Grating to listen to and his gimmick wore out fast. All the wackpackers were just human piñatas to be smacked around, but he's got to be the dullest one.
Dan Soder: You could always tell that he was treating his appearances as a potential "big break" for him, which led to him giving off this uncomfortable and kind of forced people-pleaser energy to the show. Was good on the Bonfire, though.
Gregg Hughes: