Inside Late Night with Mark Malkoff - The Bill Carter Interview: Conan O'Brien

Episode Date: March 11, 2026

On the eve of his return to host the Academy Awards, late-night legend Conan O’Brien joins Bill Carter for a wide-ranging conversation about stepping back onto one of television’s biggest—and riskiest—stages.

Hi, I'm Bill Carter, editor-at-large at late-nighter.com. I am so excited to be able to chat today with Conan O'Brien. He's a late-night legend coming off an absolutely spectacular year. He got, I think, the best reviews ever for hosting the Oscars and the Mark Twain Award, which was a great show, very, very funny show. And, of course, he hosts his HBO travel show.

And he has a podcast that is much appreciated, much listened to. But best of all, he is an old friend. Yes, right. Welcome, Conan. Thanks for being here. Yeah, good to see you, Bill. Yeah, we go way back, I think, to 1993 would have been when we first met when I was starting out in late night. So I first saw you in the famous press conference said that the Rainbow Room. The Rainbow Room, yes. That was the Rainbow Room. And very hard to explain to people now. You appreciate it. But very hard to explain to people now what an unusual show business situation that was.

Because now we live in an era where there's no such thing as a complete unknown. Anyone like me starting out today would have 600 hours of YouTube clips and nonsense. It was pretty unprecedented to say, hey, there's this guy who hasn't really done anything on television performing wise. He's a writer, but he's got an interesting vibe. let's give him the most coveted slot in network television. You chronicled all of that very well. And so it's funny all these years later to be talking to you. And we're both still here.

It's been a great ride. It really has. So here you are. You're ready for your second hosting job of the Oscars. You're like a prize fighter. You've done your training. You're ready to get in the ring? Is that what you feel?

Well, how I feel, and this is how I always feel, is I will be ready half an hour before I go out. I mean, I take things up to the wire. So we've been working hard since December, thinking of some things. And then the writer's room assembled in January. And we have a lot of tricks up our sleeve and a lot of ideas. but everything's fluid up until you get to the day of the show. And that's where things get locked in. So you know me, I will never say, yep, I'm all set.

Not a worry in the world. We'll be going right up to the show. And even throughout the show, you know, if something happens, good, bad, we will have to respond to it. So this is one of those things where you're not, you can't rest until you sign off for the night. So that's how I feel now. That's how I'll feel up until this thing is over. Well, you are famous for your cold opens. No one's done more spectacularly cold opens than you.

I don't want to know what it is, but can we expect something great? You can expect something. Now, whether it's great or not, I leave to you, Bill, and your compatriots and everybody with an Internet platform. Yeah. We have something. We have a, and I think more than one thing, we've, we've made some pieces that I really like. We have some live things that I'm excited about. And you start out thinking of everything you can possibly think of, and then it's this war of attrition. What ideas followed by the wayside, what things aren't as funny as you thought they were two months ago. And then some things come up kind of late in the game that are a surprise.

So this is a fair year, do you think? I mean, I don't know how, yeah, better year for making fun of a movie. You know what I mean? You make fun of the movie. You joke about the movies. I think it's a better year for the movies, the crop of movies. I mean, last year we had some amazing films, but this year, there are films that have really touched a nerve with people.

You know, one battle after another, sinners. I mean, a bunch of these movies are very different, but I think they've been seen by a lot of people. They're highly regarded. We have some big stars that are up for movies. And you have a little bit of everything this year. And so I think it's been a very strong year for best. actors, best actresses, and for best picture. I agree with you.

When you were asked this last year, Coleman, I think it came out of the blue to you. I mean, you weren't anticipating this, right? Right, right. So when it came to you at first, what was your first reaction? Did you think, oh, I don't need this, this is going to be, or did you get intrigued right away? I think I was intrigued right away. I thought, you know, as you know, I had done a work. shows in the past. And I like being, I like the format. I like being out in front of people.

I like that feeling of ceremony because you can kind of play against it. I was always, it felt to me with the two Emmys that I did that it was a great device to try some comedic ideas. And so the Oscars is the granddaddy of them all, and it's been around for 98 years. And so when they called me up last year, I thought, yeah, I have to try this. I'm very curious about it. I'd like to try it. And I know it's a lot of work. And I know I'm going to put myself through some misery, but let's do it.

And I felt the same way when they asked me again. So. You again like as you were walking, Thussing. Well, yeah, I think it was pretty quick. Yeah, they asked me very quickly. And I thought, yeah, I'd like to try that again. I had such a good time the first time.

And I'm glad I did. And, you know, it's what I love the most is the process. I love having a writer's room. And in my post late night life, the thing that I've, the two things I've missed the most are having a writer's room

and having a band. Those are the two things that I was most sentimental about. And so I have an incredible writer's room. It's the same team we had last year. And I, they're just, one floor down from me right now, and I hang with them, and we first talk and pitch things that could never, ever, ever be on the Oscars and make ourselves laugh silly. And then once we get that all of our system, we talk of that ideas that maybe could be on the Oscars. And so it's, that's kind of a joy. And I like

the process of shooting things ahead of time, the meetings where we try and out how could we make this idea better? How could we make it actually work? And yeah, there are moments of feeling the pressure and feeling just the workload. But most of all, I like making things and this is a great opportunity to do that. You have, I guess Mike, is he having writing? Mike Sweeney. Mike Sweeney. Mike Sweeney has been with me since 95? 1995. They're doing to old writers too, right? Yep.

Yeah, Brian Kylie, who's been with me since 94. And he also went to Catholic instruction class with me in Massachusetts back in the day when we were kids. It's like being Marines together back in the day. And we lost some good friends. But so, yeah, I have a couple of people who've been with me. Jeff Ross, obviously, has been with me since day one. And then we have a lot of other talent we've picked up along the way. So it's been kind of joyous.

Well, the Oscars are known for being a tough room. The actual room itself, you got all these people very nervous, anticipating joy or despair, I guess. And it's known to be a tough room. And yet, you know, that's not the audience. you really have to play to. I mean, you have, I don't know, 100 people are so crazy number like that. Yep.

Are you aware of that when you're up there? I try not to think about that stuff too much because that's all an abstraction. I mean, I know what worked for me eventually doing the late night show was I got in a habit of not thinking about the people at home, just thinking about. about Studio 6A.

And I would say, if we can make it work in here, these cameras will capture that. And so that worked for me for, you know, 28 years of doing late-night television is, you know, you can't imagine all the people watching. You have to get out there and just try to harness whatever it is that's helped me all of these years connect to people. try and harness that.

And so don't overreact if the room's a little tight at first because they're not a normal audience. They're normally when I go out in front of people, it's people that really want to come see Conan O'Brien. When you're on the Oscars, you're talking to people who you're literally the last thing they're thinking about, if they're thinking about you at all. And so you need to factor that in a little bit and think, lead with what I think is funny.

Try and, you know, take, don't try. Take charge of the room. Take charge of the show. Say this is what we're doing. And do the things that make me happy. And go with that. Because if I started individually thinking about, you know, well, gee, is Leonardo DiCaprio laughing right now? I can't quite see him.

Is Michael B. Jordan okay? And what about that person in Schenectady who's watching? You'd go mad. You'd go insane. Mm-hmm. Last year, as I said, I thought it was maybe the best reviewed Oscars I remember. Did you know, you walked off the stage at the end of that show? Did you know, okay, I killed?

I felt like I had fun. And if I have fun, it's really that simple. If I had a good time, and that goes with anything, if I give a wedding toast, if I, you know, get up and speak at a do a bit at a fundraiser, if I've had a good time and I felt like there was a flow to it all and that I wasn't thinking the whole time I was just doing and making myself laugh, usually 90s. 99% of the time, that means it went well. Or there was a gas leak somewhere and I'm diluted. But I'll go with the prior one. So I think I just thought, well, that was fun. I had a good time.

And the feeling I really go for is that feeling you have when you did what you wanted to do. You did it the way you wanted to do it. And you walk off and you think, well, if someone doesn't love, like it, I'm okay. The bad feeling would be, gee, that wasn't what I wanted to do. Those ideas didn't work out the way I wanted them to. And, you know, that can happen too. But I think it's all about that just very simple feeling that goes back to making your friends laugh in the playground you know, 50 years ago, which is, was it fun? And that's how I felt.

Well, we talked about your preparation and what you might do in the middle of the show. It's always struck me as interesting when something does happen and there's an opportunity. You don't know that at that point, you've not tried that joke out. You've not tried to make coming out. It has to be a misdious. And it's your call at that some point, your writer is going to say, hey, Conan, you could say this. Right? So it's all based on your Instagram.

Right? Yeah. Is this to the work or not? Yeah. Is that a little scary? It's actually, sure. It's not as tried and true, but I think you get points for trying something in that moment. So it's a little bit like an Olympic dive.

You get graded on the difficulty of the dive. If something has just happened, people are looking to the host. to guide them through that and maybe to talk about what everyone's thinking about. And if you can do that in a funny way, the potential payoff is much greater than anything you thought of three months ago that was well crafted and tested in clubs. So there's a humanity to this. It's a bunch of humans in a room. There's a human element.

And I don't know what it is about our species, but boy, do we know when something organic. People can really appreciate a joke you thought out or a pre-tape you did or a bit you're doing that's very well done and well rehearsed. But when something happens in the spur of the moment and you comment on it and it's people find that really exciting and electrifying. And as you know, better than anybody, if you look at back at all of the best of clips, from Johnny Carson, it's rarely a prepared bit. Many times it's something that unraveled or happened in the moment and Johnny commented on it. That is proof that this is nothing new.

You know, the streaker that ran past David Niven in the 1970s and he had a comment, that was electrifying. That's the clip they always play for. you know, great moments in the Oscars, that beats out 10,000 well-crafted jokes or really good pre-tapes. So you get a high reward if you can think of something good in a moment and you can't be too afraid to try. You got to go for it, of course. Yeah. I have to ask you because your comment at Oxford has gotten a lot of attention where you try to distinguish between anger and comedy And of course, I got exactly what you meant.

I think it was probably taken to a place you didn't expect, maybe. But I wonder if you could sort of clarify what you were thinking there. Oh, well, I think you can't talk about anything in politics these days without people wanting to put their own lens on it and take it either to the right or to the left. But I think, as I said before, It's very difficult to satirize something that is so absurd in and of itself. I think that's the main point I'm trying to make, which is the task, I think, has gotten a lot harder because you look at the headlines every day and you think, if the comedians just, if the comedians just, is to stretch and bend something. How can I stretch and bend this thing that's already absurd? It doesn't mean you shouldn't try, but I think it's much more difficult. And sometimes I think

it's easy to just let emotion take over. And the next thing you know, you're thinking, well, you're giving us our opinion, but you're not giving us the comedic take on it, which is fine, but it just it's a more difficult time to come up with the good joke. I don't envy a joke writer in a late night room right now because I think it's

really hard. How do you think of the funny satirical take on something that is so absurd every single day? That seems very difficult. But my hat's off to them for trying, you know. But as you, I think, know,

that there has to be something funny. If you're being a comedian, it's comedy that is important. I mean, like, you have to play. Well, it all depends. Everyone's, I, you know, comedy is my religion, more or less. So I take it really seriously. And I always think it has to,

I'm very passionate about some things and I have very strong feelings. so sometimes I find it easier to take my comedy hat off and put it down on the ground and then say how it is I really feel and then go put my comedy hat back on. But it could probably be very difficult right now to, and look, some people do it brilliantly. I mean, there's always still an onion headline that will bring me to tears. You know, I think they're particularly good at coming up with the, you know, you can tell that there's a lot of passion behind it, but they haven't sacrificed the comedy.

Well, you know, obviously, that these guys, the late-night guys are in a bullseye now. I mean, they're being too good government, which is remarkable. And one guy's been canceled, another guy has been targeted. Right. And actually, he was targeted. Jimmy Kimmel was targeted during an Oscar appearance.

He had a comedy. made from the White House turned into a very funny bit. I mean, I don't know that that will happen to you, but I imagine if it did, that is something you might react to. Yeah, I mean, you'd have to take it. It's case by case, you know, but we have a president who loves to watch television and I think is obsessed with television. There's times where I think maybe you should turn off the TV.

But, but, and focus. But he clearly is, you know, and he's obsessed with people's ratings and he's constantly, you know, commenting on people's ratings. And it's this level of interest I don't think we've ever had from a commander in chief. He also doesn't seem to get the idea that you do get joked about if you're in this position. Yeah, exactly. It comes with a job. Yeah, yeah. I mean, if you look at the history of it, every president almost since.

the very beginning has been mocked and ridiculed. And they, I don't think any of them liked it, but they got pretty good at pretending to like it, which is, I think, part of the gig. Part of the gig is being able to chuckle. And then when the time is right, make your own joke. Obviously, this is also a time that the whole late night genre has hit a walls in what happened with his future.

I mean, do you think it's viable? Is the format viable? Well, I mean, you would know better than me because you've been watching this thing. You've been studying it for a long time. I think my assumption has been that it's going to morph as everything does. So many things have changed. We've gone through all kinds of change since I was a kid or you were a kid. I mean, I grew up with three networks and you watched what was on.

And then that started to change. Cable came along. You saw how much that started to change the business. You know, you'd go to the Emmys. And suddenly CBS, NBC, and ABC weren't getting nearly as many Emmys as HBO. And then you saw that fracture some more. And suddenly there are more outlets and more outlets. And then suddenly you have the internet.

And people are watching their face. favorite comedian who no one else in the room has heard of. And they're watching them on YouTube. So all those things have changed how we watch, what we watch immensely. And late night TV has probably endured longer than, you know, if someone was really paying attention, they might say, well, will that endure? I think it's endured a lot longer than you'd think, given how much everything else has changed. But I think it's going to morph and change into something else. And I might be overly optimistic, but I think no one's going anywhere, meaning, yes, you will have, if you were on a network and you're doing a late night show, you know, that may not be viable anymore.

But you have all these other places you can go, and you know this better than anyone, Bill. What used to happen is you really did go away. I mean, I would have left after the Tonight Show. You wouldn't have heard from me again. But I was able to go to TBS. And then I was able to start doing a travel show with TBS. And then I was able to have that travel show go to HBO. And I was able to start a podcast.

and I'm busier now than I've ever been, and I think it's going to be the exact same thing for any of these late-night hosts. So does it have to be a show that's done, you know, from a theater on a network at 1130? That is the system that we grew up with. But if that doesn't persist for any reason, I do think that all these really talented voices are going to be heard in other ways.

I wonder if you ever miss the rush of the Daily Show. I do not. You don't? I do not. I don't. I did it. Great reaction. You know, people, the audience lust to you.

It's hard to give some. Some people think it's hard to give that up. It's, you get one life. I don't think I believe in reincarnation. So you get one life. And I spent a large chunk of mine doing that, and I really enjoyed it, and it was thrilling. And now I like trying all these other things. And there are other ways that you can go out in front of people and get a big reaction and get that kind of feeling.

But no, the day in, day out, I'm surprised. I thought I might miss it, but I do not. I'm really happy I got to do it. Very grateful, but also ecstatic that I get to do all the things that I get to do now. Well, you do exercise some of the same muscles doing what you're going to do on the Fskers. Yeah, yeah. You have an image now as being one of the more creative guys, whoever worked in late night. Oh.

And I'm the think, as you do. That's my take. Okay. Okay, good. Well, try and sell that to other people. Yeah. No, I think people were talking. now about later who's who added to the genre who walked into the genre you'd be very prominent

in that because okay i like that ideas that no one had tried before and i i personally think that's a big part of your legacy i don't know if you think about legacy but but that to me is what i would say someone when they do ask me about it well you have to include conan he he put just much on it and i guess now you sound like my mom yeah you have to include conan we don't want him at our party. Come on. He's sweet. But I'm just wondering if that you take satisfaction in that. I take satisfaction in, I think we did a volume of very different kinds of things. So that's something that I like is that, and I say we, it was a group effort. It was, you know, Robert Smigel and all these other brilliant headwriters. And then just all my writers throughout

the years were great left-brained thinkers and still are. And we, so there are just so many strange things that young people come up to me now because it's all on the internet. That's what I love. It's all out there. It all gets passed around. And a lot of it is evergreen. It wasn't tied to that day's news. It was just presenting very silly ideas and visual. concepts. And so I love that that's out there. And I can't remember most of it now because we constantly, for years, tried to think, okay, what could we do that what's, come on, let's do something that really hasn't, you haven't seen on TV. Or that really makes us laugh. And let's not care if everybody gets it who's watching at home. And we, we, we, we put.

We pushed to do that a lot. So I'm proud of that. I don't think much about legacy. To me, what's really important is that is the moments where you got to work with really talented people. And you made yourself laugh. And I think you made other people laugh. But I have no idea how much of this is going to mean anything to anybody 15 years from now. And I think it's okay if it doesn't, you know.

I think that's all right. It served its purpose. And I don't need to be thought of by anyone other than my family after I go. All right, a couple of quick ones. Would you do SNL again? Would you host SNL again? That's a good question. I think it would, you know, I don't know.

There are times where I think, yeah, probably now I might be kind of long in the tooth to do that. I never want to be the guy who comes back and goes, Hey, this is my old high school. I used to go here. Hey, kids, I'm groovy. I mean, I never say never. But if, you know, if it came up, it could be exciting to try. But I'm not banking on it and not certainly not asking for it.

I've, you know, I'll leave that to wiser people to think about. I think a lot of people would look forward to it if that came. The other thing is, I got to ask you about the hot ones. I rewatched that recently. I found it very hot. I'm also Irish Catholic and I don't eat bites. Yeah, yeah. So I watched that thinking, how on earth did he do this?

And how did he feel the next day? It wasn't the next day. It was that day. I mean, one thing I will say is everyone think that's all intestinal, which it is. That's not pleasant. But the thing that shocked me is that I was being so. I was channeling Jerry Lewis or whatever. I was, you know, getting the sauce all over myself and rubbing it into my nipples and putting it on my hands.

It burns. It's an acid. So I have this, you know, I wear a wedding ring and it got in underneath my wedding ring and burned the skin. I mean, I felt it for a while afterwards. But when I get into that kind of behavior, I will do. anything that's good for the comedy and worry about the other stuff later. And that has always been my attitude. It's a little, I was talking to Johnny Knoxville about it, you know, who's done jackass for years. And I can kind of relate to those guys because if I think something's funny,

if I think it might be funny for me to go through a plate glass window and land in a cactus, I might do it and think we'll figure this out afterwards. Someone knows where the emergency room is. So I'm not saying that's a good thing, but that's what I do. Well, you're esophagus. Well, you're in internal order. It's lower down than the esophagus. It's lower down than the esophagus. The esophagus was fine.

There's some large intestine issues. But I'm told with surgery, it will all be corrected. Have you eaten wings since then? I have, but you know, it's funny. I've had people stop and talk to me about hot ones while I'm wearing the denim jacket that I was wearing on hot ones. And I remembered that I put some of the... In the pocket. I put some of the chicken in my pocket on the interior pocket.

And when I look in there, there's still sauce. So I've been able to show fans. Like, oh, see, this... It's right. It went right in there. They're always amazed that I apparently own three jackets, but that's the fuck goes. Well, it was another fantastic thing you did this year. It was fun, yeah.

Which launched that show. That was the biggest show they'd ever done. I interviewed the host. He couldn't believe the thing. Yeah. No, it's, I have no shame, which might be my superpower. And you have no hesitation to be funny. That's certainly true.

I have to say, it's been a fantastic pleasure to talk to you again. And honestly, really looking forward to the Astros coming up. And it's on ABC, of course. Yeah, it won't be for lack of planning. I hope we have a good show. We'll certainly have a lot of ideas. And looking forward to that. And Bill, like I say, we go back to the beginning for me.

And you've always been very nice to me. So I will happily talk to you again. I just am thrilled for you. really am. Thank you. Thank you, Bill. Conan O'Brien hosts the Oscars Sunday, the 15th of March 26 on ABC. I'm Bill Carter for Late-Niter. If this is your first time listening to one of our podcasts, click that subscribe button or visit us online at late-nighter.com. Conan, have a great show. Thank you, sir. Take care. That was great.