Conan O'Brien on Taking 'Conan' on the Road and How He's Like Winston Churchill

Late night's 'Wily Veteran' discusses how Travel Conan is different from Regular Conan.
Courtesy of Turner Broadcasting System
Conan O'Brien and Zooey Deschanel on 'Conan'

[The Hollywood Reporter spoke with an assortment of the biggest names in late night about changes to the volatile variety talk category at the upcoming Emmys for a magazine story. Some longer Q&As from those interviews are going online.]

Conan O'Brien is a old hand when it comes to being late-night TV's new kid on the block

As a fresh-faced Simpsons scribe, he represented a generational shift when he took over Late Night in 1993. 

After what appeared to be an orderly changing of the guard, he found himself acclimating to the 11:30 slot when he became the host of The Tonight Show in 2009.

And following the unpleasantness of his truncated Tonight Show run, he helped shift the late-night paradigm to basic cable when he launched Conan on TBS in 2010.

Now, O'Brien is the "wily veteran" of the genre, which has received a transfusion of fresh faces and fresh shows in recent years, but venerability hasn't bred complacency.

In this Q&A with The Hollywood Reporter, O'Brien discusses how Conan has continued to innovate in recent years, particularly with the show's expanded concentration on field reports from locations like South Korea, Qatar, Armenia and Cuba. In the lengthy interview, he talks about tapping into his inner Bob Hope, why he'll never be bitter about the Emmys and his own transition to veteran status.

It sort of strikes me looking at all of the changes in your Emmy category field that you and Bill Maher at this point probably have seniority on the field. Does part of you feel kind of still like the new kid on the block?

It's funny. I wouldn't say that. I would say the changeover from being the young punk who needed to prove himself to the wily veteran happened so quickly. It's a whiplash effect, meaning the part when I showed up ... I don't know how old you are. You sound young. When I showed up in 1993, it felt to me like an eternity of being the young guy and being the new guy and being unproven. Then it felt like these 11:30 hosts who had been around — Letterman, Leno, all these guys — leave the scene, and then overnight people are offering to help me into a chair. I would say that part felt like it happened quickly. 

Then you got to do the process kind of to some degree twice, or even three times, because you got to be the new kid in a couple time slots and then on TBS. You've gone through this journey several times before.

Yes. I like to compare myself to Churchill. There have been setbacks. Now it's the 1950s, and I'm the prime minister again, but some people are wondering if maybe I have dementia. I always like a historical analogy, and that's what I'm going with.

I know that the job that you have is insanely busy and constant process. Working within the bubble of your own show, what awareness have you actually had of the half dozen new late-night shows that have launched in the past 18 months?

You know, it's funny because I'm not someone who ever, and I mean ever sat down and said, "Well, time to bone up on the new shows" or "Time to see what other people are doing," because that never helped me. I think sometimes people confuse comedy with sports, and they think, "Oh, so you must be studying the other people to see how they throw a left hook or they throw a jab, and so that you can prepare" or watching tapes of other football team. I think it's really quite different. I've always thought you're best when you just sail by your own compass. Now we're in a maritime metaphor by the way. Whenever I can just try to be truest to myself and do my own thing, and then I have an amazing web team that helps me adapt that to these times, that's when I think I'm doing my job well.

So looking at the other people ... Now that said, yeah, yes, I'm definitely aware of, I see clips I think the way the rest of us see clips. You see clips of things, and you check them out, and you see what other people are doing. To that extent, I feel like I'm aware, but I'm not a regular viewer. I don't check in. I've honestly probably wouldn't watch my show if I didn't have to. I'd be watching a dreary documentary about World War II.

So on that note, when you first came up in the '90s, there was the perception that the ways that you were pushing the boundaries were also helping push the more established people in the late night realm. It sounds like you're saying that no one coming in now can help push you because you're kind of self-pushing, I guess.

Well, I think to the extent that when I do see other people I like, I can appreciate what other people are doing, but it doesn't make me want to ... I'm trying to think what the word is. It doesn't make me change my mind about what I'm doing. It doesn't make me want to recalibrate and think, "OK, uh, you know, I should incorporate more of that into my show." I think that would be a mistake. I think the things that have felt the best for me over the last couple of years have all come about organically. They're things that I would not have done in 1993 or 1998 or 2000, because it was a different culture. There was a different technology. People watched these shows differently.

Now the fact that I can sit down with Peter Dinklage and Lena Headey and play a video game on a cheesy Game of Thrones set, and it's really fun and entertaining, but it also is relevant to all these young gamers that are out there, and it feels different than some stuff that other people were doing, it all happened organically. It wasn't a plan, but it feels like, "OK, this fits my sense of humor," as do the travel shows, which I dabbled in before, but until Cuba, we didn't really start to go at full bore.

It has felt like a natural progression. I did a Finland show in the 2000s. Lately this has felt like, "Oh, TV is different in the way these shows are watched is different, so I can take off, and I can commit all of my resources to making one really good special show, and since I've been at Turner to work the schedule around me doing that, and then have a team that's just only doing that." 

I think there's been another nice thing, which is I always did remotes. I loved getting out of the studio and doing remotes. We now have a culture where online, remotes do very well. People see them. I think, between the travel shows, which is a new thing, but the remotes, I've always done, but if you missed it, back in the old days, if you missed me playing old-timey baseball, that was it. You didn't see it. There's some of my remotes for me forming a boy band. Those are some of my favorite things I've ever done. Now, what happens is if they catch people's fancy, they're very digestible on the web. People zap them around. Then, if they like one, they drill down. A couple of years ago when I rode with Ice Cube and Kevin Hart, that was just a fun goof around thing. I didn't know that that would blow up like that. Then, when we did it again, and went weed shopping, we had a feeling like, "This will probably do well, and it's fun. These are funny guys," I like that it has a narrative. Those remotes have a narrative, and when someone likes one, now, they can click on, there's always 10 or 15, or in my case there can be 40 more, that I've done. People start drilling down. They'll say, "I watched that, but then I watched you do this, and then I watched you do that." That's the aspect of this new world we're in that I really like.

Last year, you did Armenia, you did Qatar, and you did Korea. Did that feel like the amount of travel? Could you imagine doing more than that in a year?

There were times where, especially, Armenia and Qatar happened right on top of each other. There were a few moments there, where I was getting no sleep, and feeling ... I don't know if you've ever watched that movie The Right Stuff, but there's a part where they get up really high, and the test pilot starts to see the space turn purple-blue, and then he passes out and almost crashes? It felt a little like that at some point. I don't know why. I think there are times where you run on fumes, you don't sleep much, because when you work that hard to get to a country that's hard to get to, you don't want to waste any time. You want to be shooting as much as possible. You're jet-lagged, and there were a couple of times where I thought, "Yeah, this is probably ..." depends on where you're going, but if you're going to really far places, and you're really trying to make a quality show, probably four times a year would be hard to top.

Along those lines, have you discovered that Travel Show Host Conan is different in any ways from talk show host Conan? Do you have a Tony Bourdain hat that suddenly, magically appears on your head, and you suddenly start talking differently, or acting differently?

Tats just start appearing on my arms and I try eating $3 crab off the street. I would say the biggest thing that is different about Travel Show Conan is that if you think about it, I'm not the host. I take the hosting job really seriously and when you're the host, there's an audience there and I've worked hard at it and I think it's still essentially me, but you are making sure that these different elements come together. Sometimes, you're taking care of someone, getting them through an interview, when it's really not their favorite thing in the world to do. Don't get me wrong, because I love the spontaneity of interviews, and I love when an interview spontaneously turns into something and there are great moments. That's something that still thrills me after all this time. I love the old time classic format of that kind of show that I grew up watching.

What I really like on these remotes is that, first of all, you're seeing me completely out of my element. I think people like seeing that. You see me humbled a lot, which is good comedy, because I don't know what the f--- I'm doing. I'm being schooled by these different cultures, and I'm not the host. In fact, the country's the host. I'm there. I think that's probably the biggest difference is people get to see me buffeted by these strange experiences and these people.

I'd say the one common thing, my favorite type of comedy is when the butt of a joke is on me. That's actually always been the thing that I've been most comfortable with. What fits well on these travel shows is that it's almost like a form of diplomacy, where the American goes over and they're laughing at me. Even if they don't speak the language, they can see that I'm not good at the thing that they're great at. They can see that I'm struggling and they can see that I'm out of my element. I appear foolish to them, and I just feel like, "Well, there's a sweetness to that, that I like" and that I think is not a bad way for these countries to see an American comic.

On a sheerly practical level, the international markets have become so crucial for the scripted field today, when you travel, what is the sense of balance you have to have between creating entertainment that's coming back here for the domestic audience, but also, to some degree, servicing and promoting Conan as an international, worldwide brand?

It's funny, because I should think more about that. I would say, on its purest level, I am like many comics, at core, I have a narcissistic hunger for everyone to see my stuff. That is the thing. I'm delighted when I can take the shtick that I've been working on since the 3rd grade playground in Brookline, Massachusetts, and be trying it out at the demilitarized zone in Korea or in Yerevan or at a massive air base with the first lady or in Cuba or in Korea. When I can get my sense of humor, and get people in other countries to laugh at it, that's the primary thing that drives it. Then, you'd be shocked at how little thought goes into, "This would be good for the international brand," because, honestly, I don't know. Our digital does very well, but, when I go over to these other countries, someone would have to explain to me, probably for an hour, whether or how this could be monetized, if it could be monetized at all. 

What's interesting is so much of it's fan driven. It doesn't economically make sense to dub these late night shows. It does make sense to dub Everyone Loves Raymond, and Friends, because they made 24 a year, or 22 a year, and they're half-an-hour long, and you can dub them, and you can show them forever, but shows like ours, economically, it doesn't make any sense to dub them. What's fascinating is that I don't even know. There are countries where I don't even think that they understand what the hell I'm talking about, and it's always been a barrier for our shows. In Korea, we found out that the fans dub them as a service to other fans, and put them up. That's fascinating.

There is no secret room at Conan, Conaco and Warner Bros., and I'd be proud and I would tell you if there were, where I say, "This is our master plan." There doesn't seem to be a master plan, other than my desperate need to get laughs in every single part of the world before I die.

I mentioned Tony Bourdain earlier, but how much of this, honestly, is you tapping into your inner Bob Hope, at this point?

It's funny. If you and I had talked 10 years ago, and you had said, "What's the one downside to having the perfect job?" I used to think about having my own show when I was 7, and tell people about my show. I would watch Johnny Carson and then later I would watch Letterman, and I would think, "Isn't that the perfect job?" Once I had that job, and was doing it, and was established, the one thing that I could say was a downside, and really, other than having to put makeup on everyday, which I hate, the one thing I could say that was the only downside was that you had to have your ass in the seat of that talk show chair every day, most weeks of the year, and you felt a little restrained and restricted.

I'm a curious person. I like to see things, and I like to meet people. That is the part of me that is completely, almost reinvigorated by these travel shows. I just read a great biography of Bob Hope, really fantastic. One of the best showbiz biographies I've read in a while. It's just called Hope. It came out six or nine months ago. I think he had the same thing, which he just wanted to go to these places. He obviously loved to entertain and I love to be in front of people. I love to be in front of crowds, but I really like to go places where I'm not expected to be.

I also have a personal sense of "I want to see Armenia. And I want to go to ..." There's so many places I would love to go and experience the culture. I'm a history buff, and I love seeing these things. It also happens, I think, when you've been doing this, it's been 23 years for me, the secret, now, is to find ways to be just as excited as I was in 1993, because that's the danger. The danger for me, now, is to feel like, "Yeah, I got this. I can do this for a few more years. It's fine. Wonder what I'm going to have for dinner tonight." That, I think, would kill me, creatively.

The travel shows, they just make me feel youthful. It's new. It's a new experience. When I wake up in another country, and we're driving to a Buddhist temple and it starts to snow outside, or we're driving through the DMZ and they tell us there's a million land mines on either side of our bus, I'm on my toes in way that feels exciting. I think that's part of the thing that pops when you see these shows, is you really see me, I'm delighted. I'm sure that's what Bob Hope felt or Anthony Bourdain feels like. It's just exciting.

When it comes to keeping things fresh, it makes sense how that would keep things fresh. From the outside, we assume that this election cycle has been comedy gold, but being in the middle of it, how great a challenge has it been to keep up enthusiasm with the absurdity, and having to continue to make the same jokes, as it were, for all these months now?

People say that it's comedy gold, and what they don't understand is it's a double-edged sword. I think it is for any comedian. Especially Trump, because the hardest thing to parody is something that's already inherently absurd. 

Back in the day, years ago, when I was on the Lampoon, and you would think about what are things to parody, sometimes people would say, "You know what you should do, is do a parody of the National Enquirer." You'd say, "Well, you can't." How can you top what they already have on their cover? It's so absurd, that how do you parody it? So Donald Trump is now the nominee for the Republican party. It's really happening.

Sometimes, it's hard to come up with the angle on that that's actually more absurd than the reality. Also, there's more political comedy and satire than there's ever been before and there's so much of it that you got people with weekly shows taking a crack at it, and people with nightly shows taking a crack at it and there are people online taking a crack at it. I sometimes find that you want to look for the interesting angle on it and try and find it if you can find it.

One of the things I've always appreciated about my show is we've never been overtly a political show. Whenever we've done politics, we do it in our way, but we're more silly than, probably, a lot of the other shows. We don't strictly live off what's happening in the political culture. So sometimes we can be in a political season and there might be a few nights in a row where we do nothing about the election, because it's not feeding us at that moment. That's when you'll see people in bear costumes in my audience or sketches. The travel shows are very apolitical and a lot of the remotes are very apolitical, just because that's what I've always loved the most. I've always loved the silly, and the absurd. If the election can feed that in a natural way, great. There are honestly times when I think I don't know how we can make this Donald Trump thing more absurd than the stuff you read in The New York Times.

You say they're apolitical, but when the leading candidate for one political party is talking about putting a wall around the country, isn't being global inherently very political?

Yeah. I suppose so. I suppose so. I guess, what I meant was, the idea is to make a connection with those people. When we went to Cuba, it was not an overt political statement. Some people might see it that way, but it was more about just connecting with those people. When we go to Korea, it's not overtly political, but we will have sections of those shows where we'll deal with the DMZ, and the horror that is the DMZ, or I'll take my assistant and we'll go to a Holocaust Memorial, but I've always been somewhat uncomfortable saying that my comedy has a point to make. I think it's hard enough just to try and be funny. I think sometimes, if it makes people think a certain way, that's their business, but it's never been my drive, is for my comedy to have an overt message.

This is a very varied Emmy category that you're in. Your competition includes people who air only one night a week, people who air half hour shows, et cetera. I'm curious what your thoughts are on the disadvantages and advantages, at this point, of doing every night, an hour a night, in the traditional fashion.

I've been doing that for so long, and I actually like doing shows more often, because I think some of our best things have come from desperation, when we're backed against a wall. Some of our best ideas, and you really get backed up against a wall a lot when you do a show nightly, that is something that has always benefited us. Some of our best things have come from, "I don't know. What if a dog was an insult comic? It's 2:00 on a Tuesday and let's just try it."

I don't give it too much thought, because my attitude has always been, "I got to do this my way. I got to do the kind of show that I really believe in." If that ends up getting us a nomination, or an actual Emmy, that's great, but if not, that's just the way it is. I don't want the tail to wag the dog. Obviously, yes. Especially, our category has always been apples and oranges. Even when nightly shows compete, they're often quite different, the kind of comedy they're doing. It's probably strange, just to have a competition at all, amongst these shows.

As to whether it puts anyone at an advantage or a disadvantage, I have no idea, and I think it's one of those things I just can't worry about. I'm doing the show I want to do. The stuff I'm making now, like the Korea show, for example, I'm as proud of that, or prouder of that than anything I've done in 23 years of television. The fact that I'm doing that now is really exciting to me and then getting a nomination for an award would be nice, but if it didn't happen, you got to paint what you want to paint. You got to do your thing.

Is there any small measure of relief that Jon Stewart is not going to be in that category this year?

I have the feeling he'll still win. There will be a new category, "Best Retired Host." Yeah. No. I've thought sometimes that the Emmys were just invented to give people who pretty much have had all their wishes come true in life, they've gotta have something to bitch about. I did really think that. Sometimes I've been at the Emmys, and I've seen people with just spectacular lives who get to do amazing things and when they don't win the Emmy, they're like, "I curse God. Why has He forsaken me?"

I've been there. I've been doing this a long time, and I've seen huge stars like, "Let's get out of here" and grab their wife's hand, "I feel like I've been violated." They storm out. You can picture a camera on a boom, moving up into the sky if they shake their fist at God in the rain. You're like, "OK." Then, they get into a $600,000 car and drive home to make more of a show about them. No. I won't go down that road. I'd be delighted, mostly for my staff. I have an amazing staff and they do incredible work. If we got a nod in some way, that would be very nice for them, but to say that I'm relieved, "Oh, good. Jon's not in it." No, no, no. I miss the guy, as does everyone.