Q&A with Conan O’Brien writer Brian Kiley

IDS Opinion and WEEKEND Columnist/Writer Chad Quandt spoke with Conan O’Brien writer Brian Kiley. Kiley is speaking at 7 p.m. today at the Indiana Memorial Union Alumni Hall.

IDS: How did you start writing monologues for Conan O’Brien?

Brian Kiley: One of my friends that was working on the show contacted me, and I faxed in some jokes. At the time I did a lot of topical jokes in my act. I basically sent them about 50 jokes from my act.

IDS: Transferring what you already did.

Kiley: Exactly. You know, with topical jokes in the club, you have to change them because they get dated quickly. They have a short shelf life. I sent them in, and they said, “Ok you start tomorrow.”

It’s a bit of an adjustment. Occasionally with other comics you might help them with their taglines. There are times when you write jokes and you think ‘why didn’t he pick this one?’ It’s a little bit of an adjustment for your ego initially. With stand-up comedy there are a lot more artistic licenses. You’re your own editor. You have complete creative control over what you’re going to say. If (Conan) has a joke that I wrote that does great or doesn’t do well you have your range of emotion. But if I go up and bomb or have a great show, the highs are a lot higher and the lows are a lot lower.

IDS: At least if Conan bombs with the joke you wrote, you don’t have to deal with that embarrassment.

Kiley: But I can always say, “Well, I would have done it better.”

IDS: Comedians seem to have this period of eight to 15 years of hustling before you can go onto a bigger project.

Kiley: Absolutely. It really takes a while to find your own voice and build your act. Some people start off and have very good stage presence, but they don’t have the material ... Usually people have one strength or another. You can have funny jokes but if they don’t fit you, then they’re not gonna work. That joke doesn’t fit your act.

IDS: If you don’t look like a ladies’ man and you’re doing a bunch of jokes about sex...

Kiley: There was this guy from Boston who did a seven-minute bit about buying condoms. And here’s the crowd thinking, “Why do you need a condom, buddy?” Once he changed it to, “Well I went to buy some condoms because they reached their expiration date” or whatever, that’s when they were totally with him.

IDS: Have you noticed that the internet has changed the game a little bit? Where you’re seeing fellow writers right out of college? Like Donald Glover for example?

Kiley: I think there’s always been those types of prodigies or something. Years ago there was a guy named Tony Sheehan who was like 19 and writing for Barney Miller. I think Woody Allen was 15 when he was writing. I do think there are those Harvard Lampoon guys who can write right out of college. Everybody has a different career path and peaks at different points.