On today’s excellent WTF with Marc Maron, Conan O’Brien discusses his “grim” childhood, the long saga of late night and the deep-down Catholic self-hatred that made him the man he is today. “Too skinny, too tall, my dick’s too big,” O’Brien complains, later explaining, “If I think a comedian’s too good looking…I really cannot believe they’re going to be any good. This is for us; this is our consolation prize.” Conan admits that, despite its happy conclusion, his decision to leave The Tonight Show was anything but pleasant: “In the moment, when things were really dark, I had no concept that it could all turn out.” He describes his concert series (depicted in Conan Can’t Stop) with a kind of reverence, saying “I was burning off something that was in me that needed to be burned off.” O’Brien credits his success to limiting his options to great achievement or total failure, rationalizing, “I probably have a Catholic need to suffer. That helps me.” As an Irish-Catholic myself, listening to his interview is like looking in a self-loathing mirror at my own dumb face that’s never going to amount to anything. In other words, it’s really encouraging!
Perhaps as the result of getting his ass kicked in by an Italian gang in high school, grappling with his own intensity, and almost losing his shit after seeing Don Knotts eat a Cobb salad one time, Conan remains humble about his decades-long comedy career. “I’m not a cynical person,” he says. “I can’t believe we’re all here.” As Conan’s father told him once after a performance, “You’re making money off of something that should be treated.” Good thing he hasn’t been cured yet.