Conan O’Brien Talks New Show, Late Night Changes and the Wisdom of Age

When Conan O’Brien began looking for a new base of operations, he wanted a walkable neighborhood, a space that was cozy enough to entice younger staffers to actually come in and something big enough for events. Three years later, he’s yet to host a single party. “The amount of electricity we need for all of this is heavy-duty,” O’Brien says in the top-floor office of the Hancock Park house, zoned live-work, that he finally renovated. “It took 10 months just to do the wiring.” 

Team Coco’s headquarters, often buzzing with a staff of about 30, feels more like a private club than an audio outfit. But since inking a reported $150 million pact with SiriusXM in 2022, podcasting is the main focus here. He has eight titles, including vehicles for Rob Lowe, Nicole Byer, Ted Danson and Woody Harrelson (the Cheers co-stars have commandeered a shelf of the communal fridge, reserved for their nut butters). For O’Brien — the comic hosted TBS’ Conan and NBC’s Late Night, with an infamously brief tenure on The Tonight Show in between — TV is never fully out of the picture. In fact, Conan O’Brien Must Go, a marriage of Emmy-winning travel series Conan Without Borders and his podcast, premieres April 18 on Max. With distance from his late night gigs, he’s looking at his career with renewed excitement. And as O’Brien and wife Liza are about to send the youngest of their two children to college, he’s more than a little reflective. 

As a very tall white man with a camera crew, where in your travels have you felt most conspicuous?

Look, I’m not just white. I’m maybe one of the whitest people in America. I have this Lucille Ball hairdo and I’m 6-4 — 6-5 in boots. We went to Ghana with Sam Richardson [in 2019], and at one point, I ended up at a nightclub. There were maybe 400 people dancing, and I was the only white person. I realized I’d never experienced that before. It was powerful, realizing how many times a Black person is the only Black person in a room with a couple of hundred white people. It’s an unusual feeling. 

Is that part of the appeal?

I do like to be the odd person out, the one that doesn’t fit in. I think I’m funnier when I’m not in the power position. I was talking to one guy, and he was sort of looking at my skin, my freckles, and he’s like, “Are you ill?” Those are the situations that just inherently amuse me — when a bit of the joke is on me.

How did you land on this as your next TV act? There was a lot of talk about a weekly variety show.

That whole thing cracked me up. When we were wrapping up the TBS show, there was a preexisting arrangement that we would continue on at Max — HBO Max then — and that I’d figure that part out. When it came out that I was going to be doing a comedy variety show, we didn’t know where it came from. It turned out that someone in the press department had just said something like, “Oh, that’s his category for us. Variety!” Suddenly I’m getting contacted by jugglers. Writers were calling me up saying, “Are you going to be like Dean Martin?” No, I was never going to be the 75th person to try and bring back the hourlong variety show and have it not work. 

What do you miss most about the nightly gig?

I miss that band terribly, the way you miss a lost limb. I’m an amateur guitarist, and I got to play with those guys every day. It got to a point where they had a hard time getting me to rehearse the comedy. I swear to God, if someone got me a job as a rhythm player in some rockabilly R&B band, I might disappear. You might never see me again.

And the least? 

The volume. The over and over again with multiple guests a night and making sure they plugged their projects. These shows exist because they’re promotional machines. I always understood that. My goal was to make it as creative as possible with everything else. But over almost 30 years, you get to a point where the oil doesn’t get to certain parts of the machine. I started to burn out a little bit. One of the things I love about the podcast is that most people don’t come on to promote. 

What have you learned about yourself in the shift to longer-format interviews?

I don’t know that this would’ve had the same appeal for me at 30. I’m 60, I’ve been working for a long time, and it seems to be a nice fit for me at this age. I’m curious about people and maybe a little more thoughtful than I was when I was 30 and just determined to get my career on track.

At 30, you’re often more interested in the sound of your own voice.

It’s funny you say that because I don’t particularly like the sound of my voice. I don’t have a broadcaster’s voice. I always thought that I had to compensate for that with the comedy, or maybe the hair as a distraction on some subconscious level. As you get older, you start to accept things. I’m not James Earl Jones.

You got into business with SiriusXM right before the podcast boom seemed to implode. How’s that transition been?

That’s what it feels like, yeah, but it hasn’t been difficult at all. The reason that I wanted to be with SiriusXM was that I wanted everybody to be able to hear the podcast. I love the connection I have with people. I cannot tell you how many times people have walked down the street, with earbuds in, and told me, “Hey, I’m listening to you right now.” SiriusXM was interested in us having a channel, and that seemed like a great way to keep things moving. 

Did you approach anyone for advice? Howard Stern has been in business with them for nearly 20 years. 

I’d be intimidated to call Howard. I’m worried that he’d put me on the air. We would be having a really good conversation, and then he’d ask me, “When did you lose your virginity?” with 30 million people listening.

Do you have any predictions of how late night is going to evolve?

It’s already happening. [James] Corden’s show was replaced with a different format [the game show After Midnight]. That’s going to happen more and more. When I got into late night in ’93, I was still dealing with a captive audience. Someone could actively dislike Conan O’Brien — and many did — but if they had insomnia at 12:35 a.m., there were only a couple of choices. I was in people’s bedrooms, whether they wanted me there or not … there’s a terrible pull quote! That’s not the case anymore. Everyone is siloed, in their political beliefs and their entertainment. 

What does that mean for your former peer group? 

An era is definitely over or ending. But this whole idea of it being called “late night”? That’ll probably disappear. It’s all digestible stuff for the internet, which is better produced and has better stars than a lot of what’s out there. But a Jimmy Fallon, Jimmy Kimmel or Stephen Colbert, these are talented people. I don’t fear for them.

In prepping for this, I went back to a lot of stuff from 2009-10 …

Better you than me! (Laughs.)

The Wikipedia entry about NBC’s indecision over you, Jay Leno and The Tonight Show is longer than those summarizing many wars. With distance, how do you look back on that chapter? 

Enough time has gone by where I can see that it didn’t have that much to do with me. I was standing on a fault line. We kept trying to cut this baby in half, Solomon-like, and it wasn’t working. But it just seemed to catch people’s imaginations. And that moment became about the internet, which had existed for a while but was still completely undervalued by the suits. At the time, they were saying, “What the fuck is going on? How is Conan doing this?” I wasn’t doing anything. But if you were a certain age and online, you were probably on my side. I still have people come up to me and say, “That really made me angry what happened to you.” I’m great! Someday, I’ll look at that Wikipedia entry, but 2009 feels like 500 years ago to me.

I’ve never heard your take on this, but is it true that your NBC boss, Jeff Zucker, had you arrested when you were both at Harvard?

Oh yeah. The Lampoon was the comedy magazine that I ran, and the newspaper [which Zucker ran] was the Crimson. The Crimson people go on to serious jobs. The Lampoon people are alcoholics who end up writing Animal House. There’s always been a rivalry. So we stole that day’s papers from the Crimson offices and kept them in ours. The protocol was for the other party to go, “Oh, you wise guys! Give us our paper back!” And it’d get worked out.

But not this time …

So, there’s the campus police and the nuclear option: the Cambridge Police. They’re not fucking around. So when there was a knock at the door, I was thinking I’d see the Harvard police, who’d be like, “Oh, hi, Conan!” It was Cambridge, and they started to put cuffs on me. That’s when I said, “Gentlemen, I will tell you where those newspapers are.” I folded like a cheap tent. 

Between SNL and Late Night, you worked with Lorne Michaels for 23 years. What’s your take on the retirement talk?

If you took an X-ray of Lorne Michaels, you would see SNL in his bone marrow. I just don’t see it happening. And I don’t think anyone’s anxious for him to go anywhere. When Franklin Roosevelt died suddenly in April of 1945, he’d been president for 13 years. There was a whole generation that only knew him. Lorne is the FDR of comedy. Retiring to his blueberry farm? I’m not buying it. 

You and your wife are about to be empty nesters. How’s that affecting your outlook on what’s next for yourself?

We will be in the fall, unless my son ends up going to a college that’s at the end of our street. My wife is in a slow panic. I suppress my emotions to the point that I’m not even aware of them. I have not processed it, and it’s equal parts exciting and terrifying because I don’t know, professionally, what it means. Clearly, I can still travel around and shoot these shows. But the mind boggles at the possibilities.  I could also lose my mind. All the podcasts next year will probably just be me drinking and ugly crying.

This story first appeared in the April 10 issue of The Hollywood Reporter magazine. Click here to subscribe.