The Late Show host also revealed that, as a performer, he often gets depressed when he’s not in front of an audience. “What’s that like, to be a needy performer?” asked O’Brien. “Who’s only happy when they’re getting laughs and, without it, they feel shallow and empty?”
Changing the subject, Colbert also recalled that his father had seen O’Brien perform once. “You’ve taken something that should be treated and turned it into an occupation,” he quipped.
Colbert replied, “I’ve turned my mental illness into a business model.”
Colbert, who was actually a rejected writer for O’Brien’s show, recalled the era while revealing how it inadvertently helped him celebrate his 25th wedding anniversary with his wife Evelyn McGee-Colbert.
“I wanted to do something special and when we first started dating, she lived in New York and I lived in Chicago and there was no internet, we couldn’t afford telephone calls so we wrote each other letters almost every day,” Colbert said. He revealed that he and his wife have “hundreds of letters to each other,” to which Conan called him a “Civil War veteran.”
Colbert told the Conan host he wanted to get some of the letters out to read them to her on their anniversary. To subtly find out where the letters were, Colbert told his wife, “Remember when I applied to be a writer on [O’Brien’s] show? He called me because he is ending his present show and is going to change up his show. For the end of his show, he’s having people who submitted to his original shows after 25 years come on and read some of the original pitches to the original show.” Colbert said he couldn’t find the original pitches and that the last time he saw them they were in the boxes with the love letters.
The next day, Colbert said, O’Brien ended up changing his show. “I didn’t know. I made that up as a lie to my wife.”