Playboy Interview: Conan O'Brien

A candid conversation with the once and future king of late night about his new show, his Irish dark side and those pesky troubles with NBC

People of Earth: Conan O'Brien is back on TV In a divorce that was bizarre even by Hollywood standards, O'Brien spent 17 years working for NBC, then left his job in January—less than seven months after tak­ing over as host of The Tonight Show—when network executives announced a. plan to move him back lialfan hour and. insert Jay Leno at the 11:35 p.m. spot. In reply to NBC, O'Brien, issued, a tart, defiant press release addressed to "People of Earth" in which he said the net­work's plan would "seriously damage what I consider to be the greatest franchise in the history of broadcasting." Lawyers and. man­agers negotiated a severance deal in excess of $30 million, and O'Brien, left. NBC petulantly removed his mime arid, image from its website and. returned. The Tonight Show to Jay Leno, whose poorly rated 10 p.m. variety show had contributed to the lower ratings that mused, the network to grow dissatisfied with O'Brien. Got that?

Although O'Brien lost the most coveted, job in comedy, one that usually brings longevity, he won respect for standing up to NBC, shar­ing his severance riches with his staff and bringing a fiery quality to his final shows. "I just want to say to the kids out there, you can do anything you want in life," he told viewers. "Unless Jay Leno wants to do

it too." NBC. honcho Jeff Zucker—who in September was relieved of his job—swiftly denounced O'Brien's remarks as "nasty," which mostly showed how unaccustomed TV honchos are to hearing the truth.

If this was the first time anyone had called the amiable O'Brien "nasty," it wasn't the first time NBC had expressed doubt in him. The son of accomplished, professionals—his dad is a doctor and his mom a lawyer— he was raised in Brookline, Massachusetts, a large boy in a large Irish Catholic fam­ily, and went to Harvard, where he rose to become president of the Lampoon, an august humor magazine that had been spawning successful comedy writers for more than 70 years. After graduating in 19H5, he began his comedy career -writing for an HBO show, Not Necessarily the News, then proceeded to Saturday Night Live and- The Simpsons.

In 1993 David Letterman vacated Late Night on NBC after the network chose Leno instead of him to host The Tonight Show, and Saturday Night Live creator Lome Michaels picked O'Brien to replace Letterman. It was a risk and quickly seemed like a failure—-ratings were low, and a prominent TV critic, who described O'Brien as "a luring collage of annoying nervous habits," called, on NBC to cancel him. Which, O'Brien revealed in

a 1998 Playboy Inlet view, NBC did, before it realized it had no replacement and gave him a reprieve. Within, a few years his audi­ence was Ixirge and loyal enough that NBC promised him the network's prize job, host­ing The Tonight Show.

This summer, while O'Brien was plotting his new 11 i>.m. show on TBS, pi.wboy con­tributing editor Rob Tannenbaum inteniiewed him in a Burbank office so new it was fur­nished with little more than a desk, a few chairs and a giant poster of O'Brien sidekick Andy Richter, put up by Richter himself as a prank. "When I commented on the lack of decor," Tannenbaum says, "Conan's answer was, 'Everything in this office is designed to come down quickly, in, case there's trouble and we need, to gel out of here.' A few limes he said he was tired, of being asked, about what happened, at NBC, but then a few minutes later he'd make a joke about it. Emotionally it's difficult for him, but comedically it's an endless source of punch lines."

PLAYBOY: So a funny tiling happened on the way over here, fay Leno called and said, "You doing anything today? Want to come over and interview me?" O'BRIEN: [Does Leno impression] "Do me instead!" Well, you'd better get over there.

It's close by. We're in Burbank, and NBC is not far away.

PLAYBOY: I low far are we from his office? O'BRIEN: I think if I worked out and had help with hydraulics we could hit it with a tennis ball.

PLAYBOY: Ale you in any danger of bump-ing into him?

O'BRIEN: No. He's a guy you hear coming a long way off. There aren't many three-cylinder engines in California tiiat run on peat moss. And we hang out in different circles, so I don't think we'll be bumping into each oilier.

PLAYBOY: Have you been experiencing deja vu as you prepare the new show? O'BRIEN: Yes, strong deja vu. We had a meeting with the same two set design­ers who had done The Tonight Show, and when they started to show me models of a talk show set, I thought, I was look­ing at a model with you guys 15 months ago. That last project had such a long buildup, and so much thought and work went into putting it together, that imme­diately starting to set up another one is a strange experience. This is our pirate ship—that's how I think of this show: I was on a big cruise liner, a light erupted, and I jumped off. And now I've created a pirate ship with antique cannons on it, and I'm looking for trouble. PLAYBOY: Tliis is tlie third time you've cre­ated a show.

O'BRIEN: I'm going for the record of seven in a four-year span, held by Charles Nelson Reilly. I'm going to become a mercenary: Drop me into any hot spot in the world with a desk, a microphone and a chair and I will put together a talk show, get it pretty well lit, get an audi­ence in there—and evacuate. Then it's up to the local government to keep the show running.

PLAYBOY: Is Andy Richter part of this team of guerrilla talk show experts? O'BRIEN: Andy will be part of it, for brute strength alone. Andy is the stron­gest guy on television. He's a man-child, an incredibly powerful human being. He could take Charlie Sheen in hand-to-hand combat. It wouldn't even be close. If Charlie Sheen were sleeping and unwarned, Andy would win. And sedated. Those are the rules. Andy does very well against an opponent who's sleeping, heavily sedated and doesn't know he's being attacked. PLAYBOY: Is 11 pm. on TBS a better slot for you? The Tonight Sliow invented the late-night talk show. You can't screw around too much with that.

O'BRIEN: I feel I did it my way. I fired

Henry Winkler and Tom Cruise wax fig­

ures out of giant cannons, and I would

have continued to do those things. I

like to call this new show Plan B With

Conan O'Brien. That's the title I'm going

with—"Welcome to Plan B With Conan

O'Brien." But I do not like to overthink

these things too much, because at the

end of the day

PLAYBOY: Bullshit, Conaii. Pooplo close to you say you ovorthink everything. O'BRIEN: But I don't want to get. lost thinking how this show will bo difloront from any other show I've done. Will I ovorthink it? Yos. Do I think I should? No. How's that? At the end of the day, it's going to bo mo doing whatever is in my power to entertain people for an hour. I'll break any rule. I'll use dangerous chemicals if I have to. I will meddle with the laws of God.

PLAYBOY: You'll also be talking to actors who have now films to promote. O'BRIEN: No! No actors, no actresses. That's all going. I want to talk to people who are good at a craft, people who work with their hands, someone who's really good at putting up drywall. Or uphol­sterers. We're going to talk to a lot of upholsterers. Will I bar Tom I Ianks from the set? No, I will not. He can come, but he's not allowed to talk about his proj­ect. He's gonna keep his fuckin' mouth shut about liis project. And we may have financial penalties for guests who men­tion their projects. If Jim Carrey or Tom Hanks accidentally mentions his project,

I think the viewer should be compen­sated in some way. That would be a way to turn this economy around. Anytime someone starts to drift into "Well, the great tiling about this movie is that I was reunited with my favorite director"— bzzzzl—everyone watching gets $2,500. I'm pretty much going to pay people to watch the show.

PLAYBOY: Even on cable that could get expensive.

O'BRIEN: If you could actually make money by watcliing Conan O'Brien, help put your kids through college by watching Conan O'Brien or help get out of credit card debt by watcliing Conan O'Brien, you'd watch Conan O'Brien. You say you don't want any bullshit; I don't want to bullshit you. I do not want anyone to say, "Watch Conan O'Brien. He's going to try some new comedic ideas. He's going to blow your mind." I'm going for the jugu­lar: "Watch Conan O'Brien. You will make money, guaranteed." PLAYBOY: You're not ashamed to buy peo­ple's affection?

O'BRIEN: No. I've done it before. You think Andy Richter is really my friend? Andy is

paid to go to dinnor witli me. Everybody I work witli is paid to go to dinnor with me—and occasionally paid to call me and ask how I am.

PLAYBOY: We're Ix'ing paid to interview you. O'BRIEN: Exactly. Your talking to mo is the warmest, human exchange I've had in about eight years. My wife doesn't even exist. She's a Lands' End catalog model who shows up for red-carpet affairs. I don't, know that woman. PLAYBOY: Is she obliged to have sox witli you?

O'BRIEN: No. She said there's no amount :jf money in the world. That's still a problem. It's been a problem since high school. Prostitutes have told me, 'No deal." And I've said, "I'll give you 1100,000 in gold Krugerrands." I don't know what the problem is. I think I have an odor, which is why I'm most palatable :)n television. As soon as smell-o-vision conies out, I'm through. PLAYBOY: The last time you did the Playboy hdennew was 1998.

O'BRIEN: Who was on the cover of piayboy llien? Was it Aaron Burr's mistress? What was happening in the country? The bub­ble hadn't burst yet on the Internet. Back then everyone was worth $4 million on paper. Our musical guest every night was Pat Benatar, wearing leggings. She was good, though. PLAYBOY: Well, here's something you said

in 1998

O'BRIEN: "I will never die"? PLAYBOY: You said about doing a late-night show, "The pace will kill you." You have enough money to last the rest of your life. Why do another show? O'BRIEN: I've invested really badly. The pace does kill you. You keep going back for that; there's no other explanation. I'here are probably 35 variables that make up a show, if you think about it. Imag­ine a combination lock with 35 tumblers. How's the audience, who are the guests, what mood am I in? Add all those things up, and you can never have back-to-back-loback great shows. If you have a show that's less than great, you're desperate to have a great one. But when you have :me you feel is great, you want that high again. And it's too late for me to become a neurosurgeon or a cobbler. PLAYBOY: Was there a point when you thought, I've had enough of TV—I don't need to be on the air; I can go write? O'BRIEN: When I parted company with NBC, I honestly didn't know if I would end up with another job. I didn't know if there would be a place for me in tele­vision. But I like performing. I like making people laugh. I really like audi­ences, and it would be hard for me to retire to the Connecticut countryside and smoke a pipe. When it's really funny and surprises me and the audience can tell I'm enjoying myself, that may be one of the happiest experiences I can have. Once you're a father you have to say "one of them."

So why keep doing il? I think there's this compulsion, the way a serial killer has to kill and kill again. Are these analogies helping me or hurting me? I'm just com­pelled to make people laugh—and then quickly move to another state where my DNA can't be traced. PLAYBOY: Here's how it sounds: Your need to perform in front of people is greater than the disgust you feel for the world of television.

O'BRIEN: To be honest with you, I do not have disgust for the world of television. As anyone can imagine, I have moments of bitterness, but my overwhelming feeling is that you have to be an adult about this. When art and commerce get together, it can get bumpy. I've heard writers over the years bitch to me, "Oh, they changed my script for that show I was working on," and I would say, "You know who never had any trouble with that? Emily Dick­inson. No one bothered her. Go in your attic, write what you're going to write and then die of consumption."

Do I agree witli a bunch of things that happened? No. But I don't want what happened in January to define me or ruin my optimism about what I could do in television.

PLAYBOY: You have never been funnier than you were in 2010. The anger was good for your comedy. O'BRIEN: If I were being honest, I would say yes, I think my Achilles' heel over the years has been my need to please. I try really hard to make people happy. What I went through in January was clearly a situation where I had to make a choice between what I thought was the right thing to do and making people happy. And when I say people, I mean the suits, the bosses.

PLAYBOY: The NBC suits. O'BRIEN: Yeah, and it got contentious. And you're right, that was a new space for me to be in. When I did the 60 Min­utes interview, Steve Kroft asked, "Well, couldn't you have just sucked it up and been a good company boy?" And I said, "That's who I've been. This was the exception to the rule." The year 2010 is a seismic change. It's me saying, "I'm going to piss some people off." And that can be liberating. I have a slightly different perspective now, so it'll be interesting. I think this will be a differ­ent Conan. It's the same guy but with a higher testosterone level. It's a pill that I'm on. Actually I took the wrong pill for a while—it was estrogen, and I had C-cup breasts—but now I'm back on the other pill.

PLAYBOY: Andy must have been jealous. O'BRIEN: Andy nursed for a while. I fed him the rich milk of Conan O'Brien for three weeks. \laiighs\ This will never be printed. How does it feel doing the veiy last Playboy Intenriew? PLAYBOY: I low do you think you did as the host aiTlut Tonight Show? O'BRIEN: I've thought about it a lot, as

you know. In the short time I had it, I thought I did a good job of starting to mako it mino and putting my stamp on it. It didn't soom liko it lasted that long. [laughs ] And then I looked at the calen­dar, and it hadn't. The hardest thing I can do is give myself a grade. PLAYBOY: Good, so give yourself a grade. O'BRIEN: I can't, because it will be taken out of context. But if we say pass-fail, I think I passed. \laughs\ It was a pass-fail course. Let other people judge me or say what they want about how I did. PLAYBOY: On 60 Minutes you said, "I hope people still find me comedically absurd and ridiculous." Is it possible that come­dically absurd and ridiculous just doesn't lit on The Tonight Show at 11:30? O'BRIEN: I'm not sure I agree with that. I'm not sure what The Tonight Show will be 20 years from now. Do you know what I mean? It might be a liquid gas that is distributed through tubes. Again, you're going to say "bullshit," but The Tonight Show is supposed to be just a person coming out and being funny, in what­ever way feels relevant to that period. It has already changed a number of times;

every host has done it a completely diller-ent way. But. I don't want this interview to be me sounding off on what happened almost a year ago. [excuses himself tu go to the bathroom]

What were we talking about? PLAYBOY: You had just indicated you were tired of being asked about NBC. O'BRIEN: [Laughs\ You understand, I'm trying to take the high road, and any­thing I say can be extracted. Then it will look like I'm sitting around bitch­ing and moaning. I think in a nutshell I was given way too much time on The Tonight Show. I think a two-month try-out would have been adequate, and they were very generous to give me six months. [l.aughs\ It's really more than I could have asked for. PLAYBOY: What are your goals for the new show?

O'BRIEN: I'm going for eight months on the air. All I want to do is break my Tonight Show record. I'm a guy who wants to say I did more push-ups today than I did the day before, and the good news is, I did only one push-up yesterday. PLAYBOY: Knowing it would get great

ratings and Ix1 good for your new show, would you invite fay Leno on as a guest? O'BRIEN: He can come on as the musical guest, because that I want to see. No one knows he has an operatic range \sings as fay Leno\. No, there are certain things I will not do, regardless of the price. PLAYBOY: For people who don't know Brookline, describe the town you grew up in.

O'BRIEN: Everyone rode those bicycles with the giant front wheel. The men all had handlebar mustaches and wore arm garters. Children played with a stick and a hoop, and everyone was veiy excited because they'd built the Titanic in the ship-yards nearby. Then the crick rose and we all had to move to higher ground.

I grew up in a tough area. It was kill or be killed. There were gangs of guys in Izod shirts. Actually, it was a funny mix. I was supposed to go to the Irish Catholic elementary school but instead was sent to the Driscoll School, which was surrounded by four temples. All my friends growing up were Jewish, which influenced my comedy. I think I went to 35 bar mitzvahs. Several times I was given gifts. That's a true story—I was an exotic attraction at bar mitzvahs. It was yet another situation in whicli I stood out as a child. And so I became veiy comfort­able with the Jewish faith. PLAYBOY: Wliich serves you well in televi­sion and comedy circles. O'BRIEN: Here at the show we have a blend of repressed Irish Catholics and people from the Jewish community whom I greatly admire.

PLAYBOY: You can say "Jews"; it's okay. O'BRIEN: I can't say "Jews." I can't say "Yes, we have several Jews working here." Are you kidding? You could always insert just beforehand, in parentheses, "German accent." [lauglm]

PLAYBOY: Are the Iiish ever offended by your Irish jokes?

O'BRIEN: Actually I've noticed nobody cares if you make a disparaging com­ment about the Irish. It is the one ethnic group no one gives a shit about. 'The Irish think it's funny. "Oh, those wife-beating drunks." Irish people go, "Yes! Ha-ha! We got mentioned." They don't give a shit; they don't care.

PLAYBOY: Do you envy the Jews? O'BRIEN: I really do. I think Jewish males tend to live to 120. That's my observation. My producer Jell'Ross's heart beats once for every 60 beats of my heart. He's just got a slower temperament. He shuffles in, he has a little soup, he goes home. He will be alive 100 years from now. I come from Irish Catholic stock, and we're junk trees: We grow quickly, and then in a liigh wind we just collapse.

PLAYBOY: Alt' you glad you went to Cath­olic school?

O'BRIEN: I hate what was done to me as a child, being made ashamed of my body. And it wasn't for any Catholic thing. My naked body is something

to be ashamed of. I hat was pointed out by non-Catholics: "You've just got to cover that up. That's a bad situa­tion." I'm 100 percent Irish, and I wish I were an exotic blend. I wish I had some crazy Lutheran in there, maybe a little Calvinist or Ainish. I wish I could go out in the sun. I wish I had a nor­mally proportioned body. I'm about 80 percent leg. When I see other people walk around and their waist is where it should be, I envy them. PLAYBOY: There was a quote recently from one of your Harvard roommates,

Luis Ubinas

O'BRIEN: He runs the Ford Foundation, one of the largest philanthropic organi­zations in the country. As you can see, we took slightly different paths, {laughs] PLAYBOY: Ho said, "I don't think Conan drank at all in college." O'BRIEN: I didn't drink in college. I come from very high-achieving parents, veiy serious, hardworking Irish Catholics, and you didn't screw around with alcohol. It was verboten, to use an Irish word. F.ven when I was running The Harvard Lam-poon, which is basically an organization of alcoholics, I never drank. People ask me, "Were you the class clown?" And I say, "No, the class clown is always killed in a motel shoot-out. That ends badly." PLAYBOY: The class clown is Chris Farley or John Belushi?

O'BRIEN: I'm thinking Ted Kaczynski or the Green River Killer. I'll never for­get the time I met Steve Martin. I was at Saturday Night Live, and they said, "Go pitch an idea to Steve Martin." I was pet­rified. All I could imagine was the guy witli a fake arrow through his head, this incredible extrovert. Instead I got this thoughtful, quiet man sitting there smil­ing, rarely, when something funny was pitched. I think that may be a big miscon­ception about me. My level of intensity and hard work doesn't necessarily jibe with the guy on television. PLAYBOY: From what you're describing, you were a very grown-up adolescent. O'BRIEN: I stopped going out on Hal­loween when I was really young. I said, "Okay, there's no more time for this." When I was 18 the people I looked up to at the Lampoon were taking comedy seiiously and spending all this time on it, and then they were going to work for David Letterman or Saturday Night Live. So I took this tiling I had a natural abil­ity for and attached it to this hardworking engine that I had, which previously hail boon studying Southern literature and history. I hooked the two together and became the ultimate comedy macliine, a cyborg from the future, here to destroy you all with laughter. PLAYBOY: What comedy jobs did you dream about?

O'BRIEN: I remember thinking there were only two shows I wanted to work for: I Me Night With David Letterman and Saturday Night Live. I was a comedy snob. I wasn't

going to work on Benson. I didn't want to work on a conventional sitcom, and there wasn't a lot else on TV in 1982. PLAYBOY: What would you consider to be your greatest comedic accomplishment at SNL?

O'BRIEN: That's a hard one. I did this thing once just to make [co-writers] Greg Daniels, Robert S mi gel and Bob Oden-kirk laugh. I'd stand on the street, and as girls walked by I would say, "Look at her. She is way out of my league." I would talk about all my flaws, but I would say it in this leering, cocky way. "Here she comes. Look at her, not interested in me at all because my eyes are too small and my lips are veiy thin." It was really mak­ing them laugh, and Robert said, "That could be a sketch." We ended up going back and writing it. Tom Hanks was the host, and he did it with Jon Lovitz. We called it "The Girl Watchers." Al Fran-ken, now Senator Franken, said, "Ilow'd you even think of that?" I tend to like things that are just silly and cartoony. I think I wrote some good stuff when I was there, but I wouldn't say I changed the culture, you know? PLAYBOY: Did you find more of a place for yourself at The Simpsons than at SNL? O'BRIEN: The Simpsons was great. It was this amazing team of writers, and that show was hitting on all cylinders when I got there. But I missed the adrena­line of doing a live television show. The movie My Favorite Year, that's what I miss. My whole career has been an attempt to get at the core of real show business, old-time show business. Sat­urday Night Live was cue cards, running backstage underneath the bleachers— all that crazy, exciting, scary stuff. You'd walk backstage and see people in horse costumes. With The Simpsons we were in a room with hilarious people, but I wanted to be around the makeup and the horse costumes. PLAYBOY: Are you saying that as of 1991, you had not distinguished yourself as a comedy writer?

O'BRIEN: I think I had distinguished myself and had made a name for myself, but I always felt I wasn't there yet. The analogy I had was when you're trying to get on a highway and find yourself on a road that runs parallel to it. I always had that feeling, and 1993, for better or worse, was the year I jumped onto the highway. I almost got killed—three semis came up right behind me. It was gut-wrenching madness. But when everyone else thought, Oh, this guy's going to get canceled any second, I remember thinking, I'm on the right road now. I always had this dim feeling that I needed to get my own little show somehow. I used to talk about it in college. Friends still remind me that I used to tell them, "Someday I'm going to have a show." And they would say, "Yeah, you proba­bly are." They kept me talking until the paramedics arrived.

PLAYBOY: So all along were you planning on how to get your own show? O'BRIEN: I couldn't have made 1993 happen in a million years if I'd wanted to. So many things had to go right and wrong for me to get that opportunity. Replacing David Lellerman from com­plete obscurity—I'm not smart enough to figure out how to do that. You're talk­ing to someone who got hit by a meteor. I have to give myself some credit; I think I had something to oiler, but I was more myself auditioning for that job than I was for the first year and a half on the show. At the audition I thought, Come on, this isn't going to really happen, so watch this. And I acted like a complete ass. Once they handed me the respon­sibility of doing the show, it felt like, Oh my Clod.

PLAYBOY: What were the first words you said to your wife when you met her while shooting a segment for I Me Night? O'BRIEN: We went to an advertising agency and I started acting like an ass. Almost immediately I asked her, "Do you have a boyfriend?" And she got really red. Then I started talking to her exclusively. PLAYBOY: What was her answer to "Do you have a boyfriend?"

O'BRIEN: She maced me and we had to rinse my eyes out. She probably thought, she'd never hear from me again. PLAYBOY: Were you just pretending to flirt? O'BRIEN: You could tell I was really hit­ting on her. My pants were around my ankles. \laugks\ Yeah, she could tell the difference. Everyone in the room could tell. It was creepy.

PLAYBOY: You were llirly when you met her. You're also flirty with guests, aren't you? O'BRIEN: I'm good at flirting. When you're the host of a show, it's deceptive: Actresses come out, they lock eyes with you, they laugh at everything you say, they're dressed great. You're getting all the signals that since the dawn of man have meant "You are in." The first time Jennifer Connelly was on I Me Night, in 1993, she just broke my brain. All the blood went to my nether regions, and the brain died. I remember thinking, I love Jennifer Connelly.

PLAYBOY: You thought maybe you would be with Jennifer Connelly? O'BRIEN: That's what I said in the letters. Which took a while because I had to piece them together from cut-out parts of a magazine, because you don't want the handwriting traced. That was later discouraged by some assholes at the FBI. No, I didn't think I would be with Jennifer Connelly. I never saw myself as that guy. And neither did Jennifer Con­nelly. \laughs\

PLAYBOY: Was there ever a guest you llimk you could have dated? O'BRIEN: There was definitely a tiling with Liza Minnelli. If things had gone just a little differently, I could have been her closeted gay man with a weird face. PLAYBOY: Here's another thing you

said in 1998, in your previous Playboy

Interview

O'BRIEN: "I will host The Tonight Show forever."

PLAYBOY: You said, "Marriage is a leap of faith, a giving up of control. I'm not sure I can make that leap." What changed? O'BRIEN: Nothing. \laughs\ Next ques­tion. It's everything that's scary about performing—you're giving up control. It's the yin and yang of "I want con­trol and I have to give it up." I mean, I was built to do it with ladies, all kinds of ladies, and now that's forbidden. Because of some antiquated system, I cannot spread my seed. Here it is eight years later, and I still think it's the smartest thing I've ever done. But let's see how she works out in a few more years. I'm not willing to commit, yet. I always tell her she's an excellent first wife. PLAYBOY: Why did you name your son after Samuel Beckett, the most despair­ing author of the 20th century? O'BRIEN: It could have been Nietzsche. I could have named him little Nietzsche O'Brien. I just liked the name—Beckett O'Brien sounds like someone to be

reckoned with. He's going to be either a great playwright or a bartender, or both. Most of the really good Irish names had been taken by my Jewish friends. I have Jewish friends with sons named Liam and Colin.

PLAYBOY: You know a liam CJoldstein? O'BRIEN: I know an Kamon Bronstein. They're stealing our names. This isn't some crazy conspiracy theory I have, like "They started World War I!" I'm like, "Guys, we don't have much. We have cool first names. Leave this alone." PLAYBOY: And your daughter obviously

was named after Parly uj Five actress

O'BRIEN: Neve Campbell, yeah. The true Irish spelling of Neve is ridiculous. It's N-I-M-F-G-II. You can just picture some­one on their seventh Guinness: "Toss another consonant in there." PLAYBOY: {O'Brien's cellphone rings] Don't you want to answer' that? O'BRIEN: You can ignore that. It'sjust NBC asking, "Are you blasting us?" PLAYBOY: What do your kids think Daddy does for a living?

O'BRIEN: My daughter figured out pretty early that I'm famous. She said, "People

come up and want to have a picture with you, but then they don't know how to work their camera and it takes a long time and you have to help them." PLAYBOY: Have you ever done drugs? O'BRIEN: I've tried pot, but it doesn't do much for me. And I'm not one of those people who get high on life; life really does not gel me high. The concept of me on cocaine is absurd. Here's a true story: I went to a doctor for a physical when I'd been on the air a couple of years, and he asked about drug use. I said, "No." He said, "What about cocaine?" I said, "No." He said, "You don't do cocaine?" I said, "No." And he said, "I've seen your show." [laughs] He assumed I was coked up. PLAYBOY: No alcohol for you and no drugs, either?

O'BRIEN: You know, I've changed. I like to have a drink now. I like to have two drinks now. Two and a half to three drinks now. Five is just the right amount. Eight is perfect. Nine is too much, but (hen 10 is better and I become more focused, which is weird.

PLAYBOY: You've been hosting a show for 17 years. Do you feel like a comedy veteran?

O'BRIEN: I've actually been around long enough that when I look at a show from 1993 it looks ancient to me. Andy looks like a 13-year-old boy and I look like a 15-year-old girl. There's a whole gen­eration now that has watched primarily reality television, and more and more they accept only comedy that looks like a real occurrence, whether it's The Office or Rural. They're suspicious of tradi­tional comedy. Everything on You Tube is real—epic fail, guy falls down, Snooki gets punched. And so now there's this hypersensitivity to anything that's pro­cessed or fake.

PLAYBOY: Does that make it harder to do comedy?

O'BRIEN: I think it's harder to coast, just because there's so much entertainment. Anybody who has a really funny idea now can make it happen. That wasn't conceiv­able five, six years ago. PLAYBOY: But also anybody who has a not-funny idea can make it happen. O'BRIEN: That's where I come in. [laughs] I have this theory that talent in the human population has been a constant for 50,000 years. There's so much comedy now, but we're not suddenly a more talented spe­cies than we were 100 years ago. Now everyone can express themselves. The amount of water in the tub didn't change, you just made the bathtub 10,000 times bigger and the water level is low. So you've got to earn it. Why should you have that TV show? Why shouldn't it be these other 100,000 people who just did something funny on You'Tube?

PLAYBOY: You mentioned David Letter-man. Did his show have a big impact on you?

O'BRIEN: He had a big impact on not (continued on page 164)

CONAN O'BRIEN

(continued, from page 58) just me but anybody my age. I reniem-Ixt individual jokes. He had a top 10 list, "Things Lincoln Would Say If He Were Alive Today," and number seven—it wasn't even one or 10—was "Keeagh! Iron bird!" I laughed so hard.

PLAYBOY: Here are some things people close to you say: You make yourself crazy. You're too smart for your own good. You're not good with idle time.

O'BRIEN: I can get depressed. I have a very powerful imagination that's like this big lawn mower, but sometimes if I'm not careful it can turn around and run over me. I can get way too self-analytical. That's the struggle. Let's go back to the beginning of the conver­sation, when you asked, "Why do another one of these?" I do make myself crazy, I am too smart for my own good, and I do tend to overthink things. The beautiful thing about these shows is that when you say, "Hey, let's go" and the music stalls playing, then I'm cured of that part of myself. The worry part of my brain, the analytical part of my brain is shut down.

PLAYBOY: So doing a show gets you out of yourself?

O'BRIEN: Yeah, being funny and in the moment. I'm a little out of control and I really don't care. I'm bulletproof. Then I'm content in this way that's hard for me to be content the rest of the time. The list of what I can't do is endless, but I can do this. PLAYBOY: Have you always been prone to overanalysis?

O'BRIEN: When I was a kid I had an over-active imagination, and I was anxious. Someone told me that's why people drink, because the first thing alcohol does is shut down the shame center. That's how we get Jersey Shore. As my mother says, I never took things lightly. I get very dark. Having kids, that's a g<xlsend. Your kids are just a con­stant reminder: Oh, right, I don't matter that much. In a good way. PLAYBOY: Did your parents send you to a therapist?

O'BRIEN: No, they did not. There were six of us; I don't think they knew I was in the house. \lavgks\ There was a lot going on. My dad laughed really hard recently because someone said, "Oh, and your youngest child, Justin"—he was born years alter the rest of us—"when he came along and had five older brothers and sisters, it must have been a great experience for him. You prob­ably all nurtured and tk care of him." I said, "What are you talking about? It was like throwing a tire into the ape cage." It kind of was just like [makes monkey sounds J "Ooh, ooh, ahh ahh!" PLAYBOY: You said, "I get very dark." O'BRIEN: It has happened to me through­out my life. I get consumed with worry to a point where people around me think it's destructive. When I got accepted to Har­vard, I thought, I'm going to be the dumb guy here. I remember sitting in my office the first day at The Simpsons, and they told me to work on a treatment for a half-hour, three-act script. I'd never written that for­mat before; I'd done only sketches. They put

me in a room and shut the door. I remember talking to Robert Smigel on the phone, and I was in absolute despair. I gave this speech at Harvard in 2000 and tried to let them in on how many times I thought my caieer was at a dead end. I've felt that, viscerally, 15 times since I was 22. Maybe I'm due for seven more; I don't know.

I bottom out. My sister fane said to me once, "You have this need to go to the bot­tom of the pool sometimes; you touch bottom and then you shoot back up again." I get filled with despair. What's interesting is when things get tough, I'm very calm. There's part of me that maybe just likes that and is comfortable with trouble and chaos. When everytliing's line, I'm going from office to office, asking, "What did you think of the show?" "Yeah, the show's really good; I think it's gotten good." "What do you mean i\'sgot­ten good?" This reminds me of something my

dad told me. He said, "You know, it's inter­esting; you're making money oil'something that should be treated." \langhs\ PLAYBOY: How dark do things get for you? Sobbing in a darkened room for 72 hours? Self-cutting?

O'BRIEN: No, no, sorry to disappoint you. It's never not being able to get out of"bed; it's not being able to stop thinking. I'm obsessive and thinking about it and think­ing about it. People say the unexamined life isn't worth living. But don't overdo it. The constantly examined life is not worth living either.

PLAYBOY: Do you think you have OCD? O'BRIEN: I do not think I have OCD, and I've checked with my doctor 10,000 times. PLAYBOY: What have you done to be less obsessive?

O'BRIEN: I did cognitive therapy, which helped me with negative thoughts. I was

suspicious of therapy, probably suspicious of feeling good. I'm not the first come­dian to worry about this; we want to be funny first and happy second. The biggest fear is, If I get happy will I still be funny? What if you're unhappy and unfunny? Then you're really screwed. PLAYBOY: What finally sent you to therapy? O'BRIEN: I used to make myself crazy before every show. I remember think­ing, I have to make these shows happen. Sadly, it was not being unhappy that made me do it; it was the fear that I was being inefficient. I want my kids not to worry as much as I do. That's what I wish for them. I'd like them to worry some but not too much. \langhs\

PLAYBOY: The speech you gave on your final Tonight Show was very touching: "Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you're kind, I'm telling you, amazing things will happen." O'BRIEN: I wanted to end on an optimistic note. I thought it could end up being the most important moment of my television career. It still could be, unless I get shot on the air on TBS, or shoot someone. I have had too many good things happen in my career to end on any kind of bitter note. I'm just saying this to you; we're alone in this office, and I don't have to say this: I am an incredibly fortunate person. I still want that to be the message I go with. And as crazy as this sounds, my career with NBC was overwhelmingly positive until this. "Other than that, Mrs. Lincoln, how was the play?" \laughs\ The play was pretty good until that part. The entertainment business has an amazing way of turning really lucky people into bitter, angry, rage-filled, jealous, resentful wretches who can't believe they got screwed. Some things have worked out great for me, some things haven't. You keep going. PLAYBOY: Has the dust settled? O'BRIEN: I think the dust may not settle for years. Think of an emotion, and I've had it this year: anger, despair, elation. Doing those last Tonight Shows was a high. A lot of people tuned in, and I was really proud of what I was able to make in that situation. So this was good, this was bad, this was ugly, this was beautiful, this was fucked-up, this was sublime. It was cherry, it was vanilla, it was frogurt, it was mocha chocolate chip.

PLAYBOY: Can we end this interview, like your final Tonight Show, on an optimistic note? O'BRIEN: I cannot tell you how, but I think I'm different now. Here's an incredibly nerdy reference: In the first half of the Lord of the Rings movie, Gandalf tries to get over a bridge and falls down a hole. The dragon pulls him in. He's gone, and you think he's dead. Then he shows up late in the movie and he's not dead. They don't quite explain what happened, but he's all white now. He has been through some incredibly trans­formative event; he says he fell and he fell and he fell, and then he comes back, and he kicks ass. I tell my writers I'm the white Gandalf now. 'The guys who work on my website like that one.

/ don't want anyone to say, "Watch Conan. He's going to blow your mind." I'm going for the jugular:

"Watch Conan. You will make money, guaranteed."

If I were being honest, I

would say yes, I think my

Achilles' heel over the years

has been my need to please.

I try really hard to make

people happy.

/ remember thinking there were only two shows I wanted

to work for: Late Night

With David Letterman and

Saturday Night Live. I was

a comedy snob.