Watching the classy late-night transition from Jay Leno to Jimmy Fallon and David Letterman to Stephen Colbert, it is hard not to feel a little badly for Conan O’Brien and the way he was set on fire several years ago when Leno grudgingly handed off the Tonight Show torch to him — and then refused to go away. NBC’s unwillingness to commit to O’Brien despite his lengthy tenure in the 12:30 slot created the biggest bungle in late-night history. A large financial settlement didn’t ease the sting of O’Brien realizing his dream of filling the seat once occupied by his idol Johnny Carson, only to lose it seven months later. O’Brien’s long past that, now, and comfortable and confident in his 11 PM slot at TBS with a show as strong in quality viral video bits as Fallon’s and Jimmy Kimmel’s, and a mischievous spirit that seemed to have gone missing when O’Brien tried catering to the masses from that cavernous Tonight Show set. His show is as sharp now as any time since the lanky redhead came from The Simpsons writers room to NBC in 1993 and honed his distinctive, self-deprecating style for the college and insomniac crowd. Here, O’Brien talks about his place in the shifting late-night landscape, and how social media has played to his strength.

conan ice cubeDEADLINE: Your TBS show recaptured something lost during the Tonight Show stint, that “I can’t believe we’re getting away with this, don’t tell the grown-ups” vibe. What’s the biggest difference between the show you do now and the one you did for so long at NBC?
CONAN O’BRIEN: The biggest difference is how much social media has changed the DNA of what I do. I came up in the old system 21 years ago, when Carson had just retired and there were only a couple of us doing this. It felt then like I was the awkward kid in the tree house, looking down on the adults. When we started the show at TBS, I had to jump into social media overnight. I didn’t even have a Twitter account, but it was so important in launching my national tour and how I stayed alive during that down period after The Tonight Show.

DEADLINE: It seems the viral videos have become as important as star guest bookings, in building audience awareness.  What’s the biggest benefit to you in this evolution?
O’BRIEN: For me, it’s the ability to play to my strengths as a reactive comedian. I’ve always shot remotes, but there is more immediacy to them now because we shoot them so quickly. Whether it’s me playing video games or something else, there is a seat-of-the-pants reactive quality to them. I’m at my best when it’s me in an absurd situation. Me, in the American Girl store. Me, the whitest man in America, in a car with Ice Cube and Kevin Hart trying to score weed. With this show, it came down to me having to make a choice of doing it the old way, or growing. That has been the biggest single difference social media has made. I always liked reacting and improvising, and that plays so well into what this world is all about. It isn’t something that could have happened 10 years ago because that world hadn’t ripened enough.

conan at&tDEADLINE: It must be invigorating not to rely on the formulas and touchstones from years past, as many late-night hosts of the past did.
O’BRIEN: I’ve checked off so many items on the list of great moments that I hoped to have in television and now, it feels to me that the only reason to continue doing this is if I can find ways to surprise myself and have fun. I really want the show to keep evolving — that’s the thing I’m almost religiously driven by. I’m constantly questioning. I don’t think there’s one bit from the old show that we do now, and I think there’s probably a bunch that we could do. I just said, “We should take this as an opportunity to make ourselves work, and rebuild from the ground up.”

DEADLINE: That attitude certainly leads to surprises. You mentioned video games. When you took the show to Texas, you played them on the oversize hi-def screen Jerry Jones built in AT&T Stadium for the Dallas Cowboys. Do these ideas come easy for you now?
O’BRIEN: They don’t. You wouldn’t believe how much we throw out. I learned early on that most of the work in good writing is editing. My method has always been, “Let’s generate much more than we can use and let these bits fight it out and see what wins.” It’s a volume business. So there might be 150 ideas we’ve said no to when someone says hey, they’ve got the largest TV screen in the world in Dallas, and you’re like, “Wait a minute, let’s play video games on that, especially because I’m really no good at playing video games.” It’s wish fulfillment; everybody would like the chance to do that.

DEADLINE: You were always the kid in the late-night crowd. Now you’re the elder statesman. How does that feel?
O’BRIEN: It’s funny. I think I don’t mind it. For the first two years I was on the air, everybody, anywhere, was telling me, “You’ll never make it.” Some of them were family members. To find myself in this position is just funny. When I started out, if someone said, “I saw that thing you did last night,” it meant they were up at a quarter of 1 in the morning and for the first decade, they always felt compelled to explain why. “There’s this cream I need to put on my arm every three hours, so I had to set the alarm.” When we started, there was one late-night show, and now there are so many. What’s interesting is, each occupies its own niche. I am not influenced by those others. I have always tried to keep my head down, to try getting at the essence of who it is I am. That has taken me 21 years and I still think I can get better. I was in an airport recently and an 8-year-old boy was thrilled to see me. He called me Mr. O’Brien. He’d seen every gaming remote and could quote every line because, like my son, he just loves those games. You can waste time bemoaning the changes in the business if you’ve been doing it as long as I have. It strangely feels right to me that things are changing so quickly, that there are this many shows and this much noise about them. I think there’s never been a better time to play with the way the world has changed and with how the internet has changed everything. Just play, don’t overthink, and you’ll be surprised.

conanlenoDEADLINE: You seem at ease now. After that Tonight debacle with Leno, how difficult was it to get back your confidence?
O’BRIEN: It took a lot of time to process. I’m an impatient person with a really strong work ethic. My two least favorite hobbies are cynicism and entitlement. I can’t stand entitlement. So there was a big part of me that was telling myself, “OK, that happened. Suck it up and let’s move forward.” I was trying not to process it, but I had to. Looking back, some spectacular things came out of all that. There were some brilliant moments on those last Tonight shows I’ll always be really proud of. The choice is, you can either go insane or embrace that things happen for a reason. I finally just decided there must be some reason this happened, but it took me awhile to come to the fact. You can’t just put your head down and keep going, you have to feel whatever it is you’re going through. I know it sounds like someone’s been to a therapist, but when you go through something like that, you don’t just dust yourself off and forget it ever happened.

DEADLINE: Few lessons are learned in victory, most come when things go wrong. What were the most valuable things you learned about the business and yourself coming through that adversity?
O’BRIEN: There were a lot of really pleasant surprises. I had no idea I had that many people in my corner. For those many years I had been doing my show, I always called it submarine duty. You’re in the concrete box, doing your show, working all the time on it. I’m not the guy who’d hang out at the clubs at night. I would go home to my wife, watch a History Channel documentary, pass out, get up in the morning and go at it again. I was pleasantly surprised by the outpouring of affection. Lorne Michaels told me years ago, “When you’re on TV every night, eventually what’s in you comes out. They see the real you, there’s no hiding it.” What I went through put me through an X-ray machine, an airport scanner. Even though it wasn’t comfortable or fun, it happened. I was happy with the way I behaved and the way my staff behaved and how we tried to make it into something creative and fun with the tour and then reinventing a whole new show on TBS, one that feels like it belongs in 2014.

andy richterDEADLINE: You started at the beginning with Andy Richter, who came back during the Tonight Show and is now a mainstay of your TBS show. Unlike traditional late-night shows, you are generous sharing the laughs with him. How did that evolve?
O’BRIEN: It felt right, almost right away. I remember very clearly it was the spring of ’93 and I was in New York but came out here to meet about Late Night. They picked me from obscurity, with no TV experience, to take the job. I think it was like April 28 or something like that, and I had to be on the air September 13, an insanely short amount of time to go from zero to 100. We had to find all the writers and figure out how I was going to do this. Jeff Garlin, of all people, suggested I meet with this guy Andy Richter. I saw him do the Real Live Brady Bunch stage show, and knew he was out of the Annoyance Theater in Chicago. I didn’t know what he looked like and I just walked into a diner and there he is with that little kid’s face. I had just turned 30. Andy was probably 24 or something. I immediately loved the guy and we were just making each other laugh and he wasn’t even trying. He didn’t want to be the sidekick but we talked him into it and after all those years he left. I was without him long enough that a whole generation who started watching after Andy was gone didn’t know he’d been part of the show. He came back and it was like no time had gone by.

DEADLINE: Still, from Carson to Leno and all others, sidekicks know that overshadowing the host is dangerous.
O’BRIEN: I have always been a believer that authenticity has to be your coat of arms. The thing about Andy is that I really love the guy and think he’s one of the funniest people I’ve ever met. There’s never been any rules of vanity. I’ve never said, “Hey, don’t you dare catch that big laugh. Lean back and let me get it.” I’m perfectly happy to have the guests get laughs every night or for Andy to get them. Or someone in the audience, for that matter. My job is to facilitate funny stuff happening. With Andy, it’s like music. You’ve got two guitar players and you want one playing high on the neck and you want one playing low on the neck. Andy has a completely different rhythm than me, a completely different energy. What people are seeing is, “Conan really loves this guy and really thinks he’s funny.” And that’s true. In show business, there are a lot of people playing roles and pretending. Andy and I go to restaurants together and hang out and it’s real and it’s nice. They’re not good restaurants. In fact, they’re pretty shitty restaurants. Andy has gambled his money away and I’m not going to pay for those big checks.

conan stephen colbertDEADLINE: I saw your Legally Prohibited From Being Funny On Television Tour at Radio City, and recall Stephen Colbert among the guests who stepped up to help make it funny. There seems to be genuine affection among the current late-night hosts, compared to those bitter rivalry days when Leno’s manager Helen Kushnick bullied potential guests into not doing the other shows. Can you explain the cordiality, given you are all still competing for ratings and guests?
O’BRIEN: Comedy is supposed to be ruthless and cutthroat and completely and incredibly competitive. You’d almost think it would be more competitive with more hosts but, in a weird way, it allows you to realize how much we all have our own unique approach. I’m a huge admirer of Stephen Colbert, he’s a friend, and I think he’s enormously talented and does things that are very different from what I do. Everyone is putting their own stamp on their shows. I think the key is when you see everyone doing it their own way and when you get to a certain age and you’ve logged thousands of hours on television, you get this life’s-too-short thought ringing in your head. My competitiveness has always been with myself; there, I’m ruthless. I don’t watch other shows and diagram what they’re doing and try to figure out how can I do that. I get no joy out of that. Occasionally, if we’re in rehearsal and we come up with something and someone says, “Oh, that seems a little like something somebody else does,” I cut it right away. Not out of altruism, but just because it doesn’t feel good if you’ve wandered accidentally into someone else’s territory. You want to leave. Comedians are amazingly intense people. Johnny Carson was the last guy to have the luxury of thinking, “I’m the only one.” He was a completely unique talent and that was a different time. The rest of us had to grow up and accept and actually embrace the fact that there’s so many talented people doing late-night, and putting their own spin on it.

DEADLINE: How much of what you just said was forged by being knocked around a bit?
O’BRIEN: It necessary for everybody to get knocked around, at least for anyone who’s going to have anything interesting to say, whether they’re a musician or a comedian or an architect or a chef. It definitely helped mature that viewpoint. When I got into this I was incredibly young with very little experience. And then you get knocked around and put through a meat grinder at different times. It puts some hair on your chest. From being knocked around, you learn how the world works and how things can go, and so you’re not just skipping through the valley looking for a pot of gold at the end of a rainbow. You get toughened up a little bit but you don’t want to become  completely hardened.

conan obrien will ferrellDEADLINE: How did it make you feel when a competitor like Kimmel or Colbert spoke publicly about what a raw deal you got and how ungracious Leno was?
O’BRIEN: It wasn’t just them; there were a lot of people. It meant a lot to me that they would say that, but it also meant a lot that someone at a gas station would say it, or people would literally drive me off the 405 to tell me. It’s always been important to me that there’s a lot of goodwill I feel I have with those other hosts. I’d like to leave this business someday with a lot of friends. I went on a ski vacation last year with my family and we bumped into the Colberts. I got absorbed by Stephen and his large family and we spent a whole day together and I had such fun. We’ve kept in touch. I congratulated him on getting the Late Show job, I felt really good about it. I’ve had plenty of good fortune come my way. It’s so nice to come to work here at Warner Bros and do this show; Turner has been amazing to me, they let me do what I want. They said I could do this show until, I think 2065 is the official day. It feels nice to get to a point in your career where you can honestly feel good for other people, you know?

DEADLINE: How much of that camaraderie and Kumbaya spirit goes by the wayside when there’s an Emmy at stake?
O’BRIEN: Our category keeps expanding, they keep adding more and more incredible people. If it once felt like comparing apples and oranges, it’s now so fast that it’s comparing apples versus oranges versus a bank safe versus a football helmet. There are shows that are political, shows that are strictly silly, sketch comedy shows. Sometimes in our category we’re up against Barbara Streisand, or Aretha Franklin, when she sang at the Apollo. I feel fortunate to have gotten a few of those things in my career. If it goes my way, great, but I also think the danger with the Emmy or any award, is sometimes I think they were invented to make extremely fortunate people have something to be bitter about because their life has gone too well in every other way and, “Damn, I didn’t get that Emmy.” They’re saying that while floating in a big pool and getting to do a show every day. I’d be thrilled if we got nominated. We use to say it was an honor but it has gotten to the point where there are so many shows that are doing so much good work in the category that you think, “Wow, it’s a miracle.” I’m thinking of reviving the Cable ACE Award, to give myself a better chance at a trophy.

lorne michaelsDEADLINE: You mentioned Lorne Michaels and the 405. Lorne told my colleague Nellie Andreeva he isn’t with you anymore because you made the decision to stay on the West Coast and he’s a New Yorker who’s now  producing The Tonight Show Starring Jimmy Fallon and Late Night With Seth Meyers. Why did you choose to stay in L.A. and what difference has it made in the flavor of your show?
O’BRIEN: First of all, it wasn’t my decision, it was NBC saying, “You’re going to take over this franchise and you’re going to do it in L.A.” They thought of it as an L.A. franchise. At the time, I had to admit, and I still feel it, that after 16 years and maybe 2800 hours of television where every day I was trying to mock stuff in New York City, I needed a change of scenery. I think it has been good. When I go back to New York now I cannot pass a street corner without recalling what we shot there. “Oh, I remember, I was outfitted as a hotdog here,” or, “this is where Kid Rock and I tried to hail a taxi.” This move was good for creative longevity, which is mostly what I’m interested in. At Warner Bros, I’m at small, vintage 1930s lot and I really do feel like it’s that scene in The Godfather where Tom Hagen goes out to Woltz Studios. L.A. has a completely different rhythm. I haven’t changed as a person, but it might be fueling my capacity to do this with a sort of fresh take for a couple of more years.

DEADLINE: Was there a part of you that was annoyed as hell when suddenly The Tonight Show moved back to New York with Fallon?
O’BRIEN: Everything was so different with my situation that no, I wasn’t annoyed as hell. Everyone gets dealt the cards that they’re dealt and you play them the best way that you can. I’ve made my peace with that. I’m happy where I am right now and it was tough getting here but so be it.

DEADLINE: Maybe the new guys benefited from the disservice that was done to you. “Let’s not treat Fallon the way we treated Conan…”
O’BRIEN: Well, if I can provide that service…in that way I think I’m very Christ-like. I really do. I think, if all that happening to me helped others have the sweetest show business experience, then I’m happy.

DEADLINE: You’re welcome, fellas?
O’BRIEN: Yeah, exactly. Anything I can do for you kids, let me know. If me getting hit by a tractor would help you guys in any way, let me know and we’ll set it up.

conan pete holmesDEADLINE: Last question. You control the time slot after your show, picked Pete Holmes and he got canceled. After what you went through, what did you tell him?
O’BRIEN: Pete’s a very gifted and talented guy. The taped pieces that he did on his show are completely unique. There wasn’t a fit right now with TBS at 12. I’ll tell you the same thing I told him: He did himself a hell of a lot of good. He built a really funny show, he learned a lot and I think he is going to have an amazing career and that he’s here to stay. There’s so much going on, a lot of noise out there, but I’m committed to Pete moving forward. He’s an incredible asset and he will continue to do great work. Where exactly that’s going to happen, I don’t know.