Stephen Colbert in 'Sick in the Head' by Judd Apatow

To mark the release of Judd Apatow’s ‘Sick in the Head: Conversations About Life and Comedy‘ on Tuesday, June 16th, 2015, Vulture have put together an article featuring some of the best stories from the book, including three from Stephen Colbert.

Stephen Colbert wasn’t burned out, he just didn’t respect punditry anymore.
It wasn’t necessarily that Stephen Colbert got burned out. “I like the grind,” he tells Apatow. The reason why he decided to retire his conservative pundit was because he felt done with the model. “I play a character on my show, and he’s modeled on punditry, and I no longer respect my model. That’s my problem,” said Colbert. “Regardless of whether I was moving on to something else after this show, I don’t know if I could have done it much longer, because you have to be invested in your model. And I really am not. I can’t watch that stuff anymore.” Good thing he quit before the elections.

Colbert refused to look at George W. Bush at the White House Correspondents’ Dinner because then he would be “a guy worried about his bit.”
Before Stephen Colbert’s epic in-character roast of President George W. Bush in 2006 at the White House Correspondents’ Dinner, he sat next to the legendary journalist Helen Thomas, who had a lot of questions for him, like, “So, are you going to do all of your jokes?” Colbert realizes he can do it all and not be “cowed” because he’ll be in character. When Thomas noted that President Bush was also going over his cards, Colbert replied, “Oh, Helen, I can’t look at him right now … Because he can’t be a person. He has to be his ideas.” He had to be his policies, not “a guy worried about his bit at a banquet.”

Colbert and Apatow on trying to get internships at Letterman.
While Judd Apatow was desperate to get an internship at Letterman, Colbert was offered one without even trying. Apatow said he wrote a letter to “every single staff member” asking for an internship. Finally someone called him, and Apatow flew to New York with his own money only for the woman to tell him the job had been filled. He went back home and wrote “the meanest letter, using words that could end my career right now.” Meanwhile, Colbert was offered an internship when his girlfriend was interviewing for one at Letterman. He went in with her, and they asked him if he wanted to chat. They had “a nice conversation” and offered him the internship instead of her. He turned it down, because he thought, “What do you mean I move to New York and you don’t pay me? What do I do, live in a trash barrel?”

Full Article: Vulture.