Let's talk about another great Irish-American comedian. How do you think your pal Conan will do out in L.A.? Do you believe him when he says he's not going to change his comedy to appeal to more middle-of-the-roadTonight Showviewers?
I don't think he has to. He's grown up, too. I was hired to write for him like the summer before he went on the air. So I watched the whole experience of, like, launching that show and was part of it. It's crazy to think now, that when I met Conan he was 30. And he was hoping he was gonna pull it off. He seemed like an elder statesman to me. I was still in my 20s, and he was 30. And now I'm 41. I look back and that and I'm like, that's amazing. He's a really smart and capable guy. Way beyond a lot of people's intelligence. And he's got balls. Conan has brass balls. I really respect the hell out of him. But now, what is he now, 45? He's a much more relatable age for America. So I don't think he has to change everything. He's already grown into a guy who will be fine for people. And people didn't think he could pull it off when he did the first show, and I learned that he was able to because he's such a capable and focused and creative guy, so I think he'll do that going forward. I don't know how he's gonna do it, I don't know anything about what he's doing. But I would just have faith in him as a guy, that he can pull it off.
Still, sad that he'll have to retire characters like the Masturbating Bear and Fed-Ex Pope.
But if you watch the show, he doesn't do much with those anyway anymore. I mean, he's got a few that he screws around with, and there's sort of a feeling that 'This is the part of the show where people have already gone to sleep, so let's try this silly thing.' But a lot of those are already worked out of his system anyway.
You've written for both Conan and Letterman. How do the experiences compare?
With Conan, we got to start a new show, and we were given free reign because we were like charter member writers, and they were very different experiences just because of where I was on the show. Probably if someone, a young guy, a 27 year old went and got hired on Conan now as a writer, they'd probably have a similar experience as I did writing for Letterman back then: which is, it's a show that's already established, it's got its own rhythm, and everybody that works there is a bit older than you, and you've got to find a way to fit into a place that is already legendary. That's really your Letterman. I was really in a weird place because I had just done Conan for two years, and I was really burnt for both formats. I did Letterman for three months and just left. Because I wasn't in a good place to write for another talk show. It felt more like school than work to me. Like I had assignments that I had to do. But I was a big fat baby and a spoiled brat, having come from Conan where, if you wrote the bit, you ran the show, that's what they did at Conan. If they ran your bit, it was entirely your baby. You cast the actors, you edited it, you directed it basically. Letterman, it was like "Give us your Top Ten jokes and go back to your office."