Conan O’Brien
The comedian on being late night’s elder statesman, losing ‘Tonight,’ growing up Catholic, and the time Trump stormed off his show
Stephen Colbert recently called you “the living history of late night.” How did that make you feel?
I felt he was measuring me for my casket. It’s funny how my career flipped so quickly. There’s years and years where you’re the kid. I used to walk into a restaurant, and people in their fifties would look at me with disdain. Then, overnight, it flips. I am technically the guy that’s been in late night the longest. What I find fascinating is because of YouTube I’m constantly accosted by 18-yearold skater punks. As long as it’s keeping them from doing schoolwork, I’m happy.
What’s the biggest lesson you took from losing The Tonight Show in 2010?
If you block out all the white noise and focus on making something good, you’ll be OK. I grew up being in love with the idea of Johnny Carson’s Tonight Show and the whole mystique of it. After I got there, I realized it’s just about the work.
What did you take from your Catholic upbringing?
Constant shame around attractive women. I have this job where the most beautiful women in the world are constantly coming out, dressed to the nines, and they make eye contact with me, and sometimes it can all be very flirty. That’s confusing for an incredibly uptight Irish-Catholic boy. I do have that Catholic feeling that someone’s always watching me.
What’s the most Boston thing about you?
I grew up not expecting a lot to work out. The Patriots were a disaster, the Red Sox hadn’t won a World Series since 1918. There’s the weather — they never canceled school in Brookline, lava could be pouring from the skies — and then there’s the harsh Boston accents. There’s this powerful negativity that makes people from Boston so funny. If I had grown up in Southern California and not been Catholic, and my dad was a surfer and my mom taught yoga on the beach, and we were told early on to just enjoy our bodies and I had a girlfriend when I was 14, I don’t think I’d be a funny person.
How have you adjusted to living in L.A.?
It’s an evolutionary mistake for me to live in Los Angeles. There are teams of scientists working on sunblocks for me. I shouldn’t be living here. I’m like Matt Damon in The Martian. I ride a bike, but I wear long pants. When I’m riding near the beach, I’m dressed like a beekeeper.
What have you had to work on in therapy?
I had one therapist tell me in New York that I had the biggest conscience of anyone he had ever met. If I drop a tiny wrapper of Dentyne gum and walk 15 feet, I will turn around. The part that’s not so noble is, I think if I don’t, something bad might happen to me. Therapy has been trying to turn down the punitive voice in my head saying things like, “You thought that was a good show? Fuck you.” There are times when I get up in the night to urinate, and my wife will just hear, “Fuck, you, man. Get it together. Do better.” I’ll come back and my wife will be like, “Having a nice little party in there?” I’m trying to disassemble that and not pass it on to my kids.
You had Trump on Late Night a lot. What was he like?
I’d always wanted to ask a billionaire, “How much money do you have on you right now?” The first time he was on, I asked him. He said, “I don’t know.” He stuck his hand in his pocket and I could see his face change; he didn’t want me to know what was in there. I was like, “Come on,” and reached over and made him pull it out, and it was a condom. He said, “Practice safe sex, everybody,” and then stormed out. He told my producer, “That’s the last time I’m doing this fucking show.” Cut to seven more times: “Ladies and gentlemen, Donald Trump!”
What did you learn from being a writer on The Simpsons?
At standard sitcoms or even Saturday Night Live, they write the material and then a couple of days later, it’s shot. At The Simpsons, you keep going, rewriting it three or four times before it even gets to the cast. The animations come back months later, and you’re still editing it. It taught me to keep going back at it — something can always be improved.
What character was your favorite to write?
Mr. Burns. You could make him as old as you wanted; there’s not a figure in history you could bring up who he didn’t know. Also, when you give a character unlimited wealth and unlimited cruelty, there’s no end to what they can have in their basement.
PATRICK DOYLE