On one hand, he never should have joined. On the other hand, he was looking for his first real break into the biz as it was disintegrating. Being twitter famous and writing the occasional piece at SBNation? wasn't going to pay the bills. But big cat is just a jock sniffing douchebro. And even if you are doing a bit, at some point in the process, if all you do is act the douchebro to make fun of douchebros, you're being a douchebro. The comedian that plays the racist homophobe all day every day is eventually just hiding behind the label of comedian. At some point you have to come on the other side of the camera and make clear where you stand. Their audience is littered with the people they are making fun of, and those people don't view it as them being made fun of, because in their eyes they are being celebrated. Out of completely random curiosity, how did Colbert strike the balance? Well, he existed in the public eye before that show went big, he did interviews all the time and the way he went about it was beyond obvious. He also didn't work for a company that was openly exactly the same thing he was making fun of. If Colbert was doing the Colbert Show on Fox that would have been a different thing.