A decade ago, Conan O’Brien’s future was uncertain. He’d lost the Tonight Show to its former host Jay Leno in an embarrassing coup, and announced he was moving his late-night show to TBS. Now, O’Brien is doing fine. His new podcast, Conan O’Brien Needs a Friend, is currently the Number One podcast on iTunes. He just wrapped up an 18-city tour that has had him goofing off in front of packed theaters, and tomorrow night he will relaunch his late-night show, Conan, in a 30-minute format he describes as “smaller cookie, more chocolate chips.”
O’Brien had wrapped his tour the night before he spoke with RS, and he was still fired up. “By the end of it, I had people standing up and putting me on the phone with their boss who they didn’t like,” he says. “It would just get crazier and crazier. It was re-energizing to do all that. So between the podcast and the tour, they’ve been like defibrillator paddles — just a jolt of energy, which is, at this stage, a welcome thing.”
O’Brien called from his office to share some of the wisdom he’s learned along the way.
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. Stephen always loves to call me up and say, “You’re still alive? What’s it like to be 111 years old?” 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: “Oh, it’s that guy with the weird name and hair who does weird shit on TV.” There’s a kind of contempt. 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-year-old skater punks. I’ve met many kids who have said, “My friends and I just binge-watched four or five hours of remotes.” That’s my dream. 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?
Obviously, that was a crazy and traumatic experience at the time. But what I learned is 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.
There was a lot of good that came out of it. I was proud of the way I handled it. I was proud of the way my people handled it. We got ourselves into a new situation, and we put our heads down, and we’ve had this body of work now for eight, nine years that I’m really proud of. So I wouldn’t change a thing. I’m grateful that I got to be on NBC for all those years. I don’t bear anybody any ill will.
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.
Listen, I’ve had a lot of therapy, but when you get programmed that early that God is always watching, so if you think you could do better, God will know, and you must try harder … I don’t know. I mean, there are plenty of Catholics that didn’t get that message, but that’s the way I interpreted it.
What’s the most Boston thing about you?
I grew up not expecting a lot to work out. That’s a very Boston attitude. 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. There’s always this feeling of growing up and never catching a break. When you listen to someone like Bill Burr, I knew who Bill Burr was when he said one sentence. 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 and pick it up. 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.
Nobody really sees that side of you on TV.
Well, it’s funny, because that’s the part where there’s a disconnect. People used to say, “What would be the biggest thing that would surprise your fans the most?” I really am this person that you’re seeing. This is an authentic side of me. I really like to make people laugh. But they would probably be surprised at how serious I am about my work.
When I’m doing the show, it’s a reprieve. Once you’re out there and you’re improvising and you’re in front of people, there’s no time to think, so you just go. I’ve actually been able to be very uninhibited on television doing comedy. There’s so many things I can do on TV that I would be probably too shy to do in my everyday life. That’s why my favorite moments on the show are the mistakes. I remember when we did our strike shows and we had to work without writers, so I would just kill time. Everyone understood the context, so there was nothing I could do except completely cut loose and do anything that came into my head. I could not have sustained that forever, but those were really successful shows because I was forced to not play by the rules.
Is being on TV addictive?
Doing a show is addictive. Being in front of humans and trying to use my brain and body to make people laugh is the thing that I’m addicted to. What I’ve found is that it doesn’t always have to be on TV. In 2010, I went on this big tour across the country and played music and performed comedy and absolutely loved it. Had I not ever found a TV show again, I think I would have probably just kept doing that. I like to make stuff. If it comes out as a podcast or a TV show or a live tour, or if it comes out with puppetry or masturbating bears or however that’s going to manifest itself — if I end my career performing in malls, I’m going to work really hard to make that a really good mall show.
What’s interesting is just how the Internet has changed everything. I’m very fortunate in that the kind of comedy that I like to do has been very web-friendly. It’s pretty evergreen. You don’t need to know the context so much for a lot of it. What does it mean to be on television exactly? In the old days, well, the Ed Sullivan show is canceled, Ed Sullivan disappears into obscurity and is gone. The minute you weren’t on, you were gone, and I don’t think that’s really true anymore, you know?
After 25 years on the air, how do you stay excited about what you do?
I think the key is to keep changing. The best analogy I can make is that, if you’ve been driving for a really long time, cross-country, by yourself, you become aware at some point, “Gee, for the last 20 miles, I really haven’t been present.” That’s a scary feeling, and that’s the danger with doing a show like this with a very specific format for 25 years. Sometimes muscle memory takes over, and what people are seeing is you doing your job the way you’ve learned to do it over 25 years.
I think that’s when it’s time to pull the car over, get out, drink seven Red Bulls, roll around in a cactus patch without your pants on, hit yourself in the head with a rock, do jumping jacks, and get back in the car, and maybe start driving it from the passenger side. Now do I recommend this as a method to people out there who are driving? No, but it’s the best analogy I have. I want that to inform the half-hour program as much as possible. I want people to see me having fun and discovering new things and taking some chances. If that means that sometimes the show is a little ragged or we’re rushing to squeeze it all into 30 minutes, then fine, as long as the moments are there and they’re good.
What career advice would you give young people?
This is something that I tell young people all the time, if they’re interested in a good way to get ahead. I didn’t invent this, but it’s really true: make yourself essential. I was very aware when I was starting out that people could fire me, and they wouldn’t be worse off. Over time, through hard work and trying to hone whatever skill I had, I got to the point where it did feel like, “No, we really do need this person here. We need this Conan guy.” Everybody is replaceable to some degree, and I accept that. But you can make yourself essential. So anyone who’s starting now, don’t look for the rewards right away. I know it’s easy for me to say that in the situation I’m in, but don’t make it about the money early on. Go to where they’re making the stuff that you love. Start getting people coffee, even if you’re not getting paid that much. Then always ask, “What else can I do?” And don’t blow your own horn. Humility, work really hard, and you become essential. Then they start wanting you there.
You came from a family of overachievers.
I don’t know that I’d describe them all as overachievers, but my parents set the tone. They were these Irish Catholic wunderkinds in the late Forties and early Fifties that not only were the first ones to go to college on full scholarships, but then went to graduate school on full scholarships. My mom was one of the early women to graduate from Yale Law School. So in a way, I’m relatively uneducated. Did I move the puzzle piece forward for my people, or did I move it back with Triumph the Insult Comic Dog and the Masturbating Bear? There’s that immigrant philosophy that each generation is supposed to move the puzzle piece another step forward. I think the judgment is not in on me yet. We’ll see.
Your podcast is called Conan O’Brien Needs a Friend. Who are your closest friends in real life?
The concept of the podcast is I don’t have friends, but I do. There’s people I’ve known forever like Greg Daniels, my original writing partner, who is a really close friend of mine. I have people who I’ve met in the world of show business who are great, like Megan Mullally and Nick Offerman. I love them as people and I try to see them whenever I can. Kevin Nealon is a great guy to hang out with and is hilarious. I knew him back from SNL days. Then I have friends who aren’t in show business. One of my college roommates, we’ve been friends since 1981, when he had the lower bunk and I had the upper bunk. We’re both fascinated with nerdy stuff in American history and Robert Caro. He also likes comedy, so he’ll come see one of my comedy shows.
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.