P A R T IV

Playboy: So how do you avoid being Dave-like?

O'Brien: We have always scrupulously avoided found comedy. You never see me going up and talking to normal Joe on the street. The real word of people, dogs, cabbies -- Letterman is great at that. His genius, I think, is playing with the real world around him. Which is not my forte at all. My idea is more about creating a fake, cartoony world and playing with that.

Playboy: Are you goofy in real life?

O'Brien: My private life is boring. I've been with the same woman, Lynn Kaplan, for four years, and there ain't nothing crazy going on. Lynn is a talent booker on our show. We go to my house in Connecticut on weekends. I sit around playing guitar.

Playboy: Gossip columnists have placed you in Manhattan with other women.

O'Brien: One of them had me with Courteney Cox. Lisa Kudrow and I did improv together years ago and we went out for a while. Maybe that's why I can now be romantically linked to the entire cast of Friends. I may be thrilled with that, but my girlfriend is one of those people who believes everything they read in the tabloids. She's sitting at the table in Connecticut when she opens a tabloid and says, "What the hell?" There's a big photo of me with Courteney Cox. The story says, "Courteney's moving in with Conan."

Playboy: Did Lynn believe it?

O'Brien: No, because the story went on to say, "Conan and Courteney were seen at the Fashion Cafe munching veggie burgers." That sentence ended her faith in tabloids. Lynn knows that I would never (a) go to the Fashion Cafe and (b) eat a veggie burger. I'm an Irish-Catholic kid from Boston; I'll eat red meat until my heart explodes out of my chest.

Playboy: Do you still drive an old Ford Taurus?

O'Brien: When I got my five-year contract I moved up. Bought a Range Rover. Now I drive the Range Rover to Connecticut for the weekend, park it and tool around in the Taurus all weekend. I can't let go of that Taurus. It's an extension of my penis.

Playboy: Can you forget about the show on weekends?

O'Brien: I drive around playing Jerry Reed tapes, fantasizing that I'm some backwoods character. But even then -- you know, it's probably not an accident that people who do these shows tend to be depressive. You want so badly for it to be right every night, but mounting an hour-long show four times a week -- the pace will kill you. One night I put my fist through a tile wall. Another night, I walked off the stage, pulled an air-conditioning unit out of the wall and kicked it. This stuff I can't explain. Nor can I excuse it. But there may be something maddening about these shows. The pace is... I forget shows we did last week. That's why I can't imagine doing this for 30 years. I bet you could show Johnny Carson footage of how he shrieked as his body was lowered into acid and he's say, "Hmm, don't remember that one."

� � �I saw Jerry Seinfeld at the Emmy Awards. He said he liked the show, then he paused and said, "How do you do it?"

� � �"Do what?"

� � �"Do what you do every night for an hour?"

� � �That shocked me. This is Jerry Seinfeld, the master. A man everyone can agree is funny. And I really have no answer.

Playboy: Praise from Seinfeld must cheer you up.

O'Brien: (Shaking his head) I worry that we have hit our stride and must be headed for a fall. Because every show has an arc. The Honeymooners had an arc. People forget, but The Honeymooners was mean and depressing. Art Carney wasn't fun and cuddly yet. Even successful shows take time to find their rhythm. Then they get self-indulgent and fuck it up. Look at late Happy Days episodes. They quit shooting on location, Mork keeps visiting, and it's an excuse to spin off new shows.

Playboy: Will you fuck it up, too?

O'Brien: Eventually my only consolation may be that I get paid a lot. I'll say, "I know it sucks, but I'm getting $65 million a year!"

Playboy: Letterman said almost exactly that not long ago. When a joke died he admitted it sucked. "But I'm making a fortune!" he said. Do you really worry about losing your edge?

O'Brien: I want a living will for my career. I want the people around me to pull the plug when I become a self-parody, an old blowhard like Alan Brady. Remember him, the television star Rob Petrie worked for on the Dick Van Dyke Show? Pompous, over-the-top, over-the-hill. I don't want to be Alan Brady.

Playboy: Letterman paid you an odd compliment. "When I see that show it withers me with exhaustion," he said.

O'Brien: That's our new slogan. "Watch Late Night -- We'll wither you." But I think Dave was saying that he knows how hard it is to make a show like this every night.

Playboy: Suppose Leno left The Tonight Show. Would you like to duel Dave at 11:30?

O'Brien: Our best slot would be eight A.M.. We have puppets, cartoons, lots of childishness. I think I'm doing an OK late-night show but it's a great kids' show.

Playboy: This from Mr. Hip?

O'Brien: No. When someone says this or that sort of comedy is hip and alternative -- "Yes, these are cool people" -- I hate that. Because at the end of the day, funny is funny. People get fooled about me because I went to Harvard. "He's cerebral." But I love Green Acres. I love how Green Acres bends reality.

Playboy: Sounds cerebral.

O'Brien: It isn't. In one episode Oliver Douglas has to go to Washington, D.C. His wife says, "Darling, take a picture of the Eiffel Tower." He says, "Lisa, the Eiffel Tower ---" �Then Eb comes in. "Mr. Douglas, git me an Eiffel Tower postcard!" Now Oliver is terribly frustrated. He keeps sputtering about Washington, D.C., but nobody listens. At the end, he goes to Washington, looks up, and there's the Eiffel Tower. That is the kind of thing that made me love T.V.

Playboy: As a TV-mad college kid you cooked up scams to meet celebs.

O'Brien: I wanted to meet Bill Cosby, so my friends and I offered him some fake award. We took a bowling trophy and called it the Harvard Comedy Award, something like that, and Cosby, thinking it was the Hasty Pudding Award, accepted. So I drive out to meet his private plane. "Over here, Mr. Cosby!" And I chauffer him in my dad's second hand station wagon. Cosby sits in the backseat, picking old McDonald's wrappers off the floor, and says, "This is about the Hasty Pudding Award?"

� � �"Oh no, nothing like that."

Playboy: You tricked Bill Cosby into letting you drive him around?

O'Brien: I didn't realize that one does not pick up a famous person in a 1976 station wagon. They like to fly first-class, to be picked up in a Town Car and put up in a nice hotel. Fortunately I am not directly involved in celebrity care anymore.

Playboy: Did you bring other comics to Harvard?

O'Brien: Yes. John Candy's people warned me that John was on the Pritikin diet. They gave me strict dietary instructions. John immediately ran into a bakery on Harvard Square to get pastries. He said they were Pritikin eclairs.

Playboy: You once stole a famous television costume.

O'Brien: When Burt Ward visited Harvard there were fliers all over the campus: Burt Ward to Appear With Original Robin Costume (Insured by Lloyd's of London for $500,000). In fact, Burt Ward was said to keep a bunch of them in his car; he'd pass them out to impress girls. Naturally, I wanted to screw with him. A few friends and I attended his speech at the science center. We went dressed as security guards. I said, "Mr. Ward, I've been sent by the dean to safe guard the costume." As if it were the Shroud of Turin. But the guy is humorless. "Yes, very good. That costume is very valuable," he says.

� � �That's when we hit the lights. Which works great in the movies. In the movies the lights go out and suddenly the jewel is gone. In real life, though, what you get is some dimming. You hit the lights and people can see a little less well.

Playboy: Did you grab the costume?

O'Brien: We grabbed it and the chase was on. Some Burt Ward admirers -- young Republicans, I guess -- took off after us yelling, "Stop them!" But we escaped in a waiting car. We proceeded to torment Burt Ward for hours on the phone, saying, "This is the Joker, hee-hee-hee. I've got your costume."

Playboy: How did Burt react?

O'Brien: Robinlike. He said, "Return it or you will feel my wrath!"

Playboy: Burt Ward used to tell reporters he had an IQ of 200.

O'Brien: He may be delusional.

Playboy: Were you always starstruck?

O'Brien: Stars are fascinating. When I was a writer for Saturday Night Live, Robert Wagner did the show. One day he was sitting offstage, talking on the phone. He had on a camel-hair jacket, silk scarf, and of course his perfectly arranged Robert Wagner hair. "Very good, goodbye," he says, and hangs up. Suddenly his hand shoots up and touches the right side of his head, where the phone reciever may have disturbed a few hairs. At that point you know he has done this smooth move every day since 1948.

Playboy: You seem to prefer goofy celebs -- Jack Lord, William Shatner, Robert Stack. There are photos of Stack and Adam West, TV's Batman, here in your office. Do those guys know you are making fun of them?

O'Brien: I'm not. I have a real affection for those men. To me, meeting Andy Griffith is just as interesting as interviewing Allen Ginsberg. I'm interested in Martin Scorsese and Gore Vidal as well as Jaleel White, TV's Urkel.

Playboy: How do Gore Vidal and Urkel compare?

O'Brien: I'd say Jaleel White's prose style is not taken as seriously. But the same is true of Vidal's nerd character.

Playboy: As one of the writers on The Simpsons you helped create some memorable characters.

O'Brien: What I loved about The Simpsons was that it wasn't a cartoon for kids. A cartoon might look like the friendliest thing in the world, but we were subversive. I loved it when we had Lisa write a patriotic essay in school: "Our country has the strongest, best educational system in the world after Canada, Germany, France, Great Britain..." It was this great sugarcoated cutting remark. I loved her for it.

Playboy: Tell us a Simpsons sercret.

O'Brien: When Dan Castellaneta started doing Homer's voice, he was doing Walter Matthau. Like I said, it takes time to find your rhythm.

Playboy: So are you satisfied with your work?

O'Brien: Intellectually, yes. The show works. Advertisers like to buy time on it. Young people really like it. But I was a moody, driven, self-critical person before I got this show, and that hasn't changed. It's just that I now have something even more frightening than a Saturday Night Live sketch or a Bart Simpson joke to worry about. I have an hour of comedy broadcast every night. My anxiety has finally met its match.

Playboy: Will you and Lynn get married?

O'Brien: The core idea of being a comic, particularly a comic with a talk show, is control. Marriage is a leap of faith, a giving up of control. I'm not sure if I can make that leap.

Playboy: What about kids?

O'Brien: What sort of dad would I make? Maybe this job and a normal family life are diametrically opposed. Dave, Jay, Bill Maher, Arsenio -- where are your kids? Jack Paar seemed to have a normal life with a wife and child, but you don't see much of that. And I believe that your kid should be the most important thing in your life. I may not have room, at least not now. I have Pimpbot to think about.

Playboy: Another foul mouthed Late Night character.

O'Brien: Half-robot, half-Seventies street pimp. He's got a feathered hat and a metallic voice: "Gotta run my bitches. Run my ho's. I'll cut you." Right now my life revolves around Pimpbot.

Playboy: You need to settle a fashion question. You, Leno and Letterman seldom wear suits off stage. Leno likes flannel shirts, Letterman prefers jeans and sweatshirts. You wear T-shirts. Why wear a suit and tie on the air?

O'Brien: There are two schools of thought on that. The Steve Martin approach says that you're putting on a show, so dress up for the people. The George Carlin approach says all that old showbiz stuff is over, this is the new way, so wear a T-shirt. I choose a jacket and tie because that's the uniform people expect talk show hosts to wear. If I came out in a mesh T-shirt and chains it might distract people from the comedy.

Playboy: How would you describe your show?

O'Brien: It's a hybrid. If Carson defined the talk show and Letterman was the anti-talk show, where do you go next? That was the question we faced. What we did was make a show that has the visual trappings of the classic Tonight Show -- the desk, the band, the sidekick -- but with everything else perverted. When it works well I'd say my show is one part Carson, one part Charlie Rose and one part Pee-Wee's Playhouse.

Playboy: Do you have any advice for future talk show hosts?

O'Brien: You had better love the job. Some hosts don't. You can see it in their eyes. Chevy Chase's talk show -- he did not want to be there. And if that's in your eyes you're finished, because there's another show tomorrow and next week and the week after that. You can't conquer it. You can do two or three or ten good shows in a row and still want to punch a wall when you slip up.

Playboy: Can you ever conquer your repressed childhood?

O'Brien: It's always there. I still believe in moral absolutes. Murder, for instance, is wrong, unless it helps the show.

Playboy: Still, talk show hosts have perks most guys can only dream of.

O'Brien: It's great to be played over to the desk. You finish your monologue, then the band kicks in as you cross the set. Fortunately, we have a great band. Even when people didn't like anything about the show, they loved the Max Weinberg Seven. The music heightens everything. Now you are more than just a guy in a suit, you're Co-nan O'Bri-en! I think every guy should have that -- if a band played you over to your rental car at the airport, you'd have a cooler day.

Playboy: Is Andy Richter your Ed McMahon?

O'Brien: He's Andy. When we were getting started and the network wasn't sure of me, they kept asking, "Who's that Andy guy?" I think we've answered the question. Part of the show's rhythm is my energy played against the quiet steadiness of Andy.

Playboy: Is that rhythm genuine?

O'Brien: Yes. Our mentalities mesh. I'm always dissatisfied. He's the guy saying, "Hey, relax. It's good enough." My girlfriend would be happy if I had a bit more of that in me.

Playboy: Who is the guest you can't get?

O'Brien: Werner Klemperer. He refuses to revive Colonel Klink, the commandant he played on Hogan's Heroes. Which confuses me. Is he going to come up with another character at this late date -- Werner Klemperer as the aging black man or kung fu fighter? No, he's Colonel Klink.

Playboy: You once said that as a boy you wanted to be like Bob Crane in Hogan's Heroes, the cool guy who "wore a bomber jacket and wised off to Nazis."

O'Brien: I asked Werner Klemperer to do some bits as Colonel Klink. He refused. Then a strange thing happened. We're shooting abit o the West Side when Werner Klemperer comes around the corner. Pulling his parka up to his chin, just like Colonel Klink, he walks past our film crew and says, "Hello, Conan. I must say the show is very good lately. Give my best to Andy. Farewell!" It was a cameo appearance in reality. He was there, he was gone. I wanted to shout, "Hey, Werner Klemperer just did a walk-on in my life."

Playboy: Are you losing the boundaries between your life and your job?

O'Brien: There are no boundaries. At any minute Werner Klemperer may step in here and give me 30 days in the cooler. It's getting surreal. Just this morning I am going through the lobby downstairs when two girls see me. One girl nudges the other, "Look, it's the guy from Conan O'Brien!" I guess she couldn't quite place me, but she knew which show I was on.

copyright: Playboy INC.

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