20 Questions: Conan O'Brien

I became 6'4" very suddenly, and I've never quite recovered from it," says Conan O'Brien. The tall television host may be citing his growth spurt as a metaphor for his accession to David Letterman's seat on NBC's "Late Night." But O'Brien has recovered nicely from what some critics viewed as a rocky start. To use an industry term, his show began trending up in the ratings, and finally, just before his third anniversary on the air this past fall, the network that often seemed on the verge of dumping him offered O'Brien a year's contract.

Though billed as an unknown when he took over "Late Night," O'Brien had made a reputation in the comedy business as a writer on "Saturday Night Live" and "The Simpsons." But he insists he'd had his mind set on performing for years. He had studied tap dancing as a child because "I wanted to be an entertainer like Jimmy Cagney."

Although he says his dedication to rock-and-roll drumming saved him from the "classic definition" of a grind, O'Brien made his way from his home in Brookline, Massachusetts to a local college: Harvard. There he found that "comedy was almost a religious revelation, because I didn't have to work that hard at it. It wasn't like memorizing for a big test."

O'Brien was twice elected to head "The Harvard Lampoon," that incubator for the brightest and funniest. After graduating in 1985 he moved to Hollywood to write for HBO's "Not Necessarily the News" and hone his performance style with improvisation groups. The "SNL' and "The Simpsons" stints followed. When NBC began its star search for the 12:30 A.M. slot, O'Brien had his "SNL' boss, producer Lorne Michaels, place his name in the running.

Warren Kalbacker met with O'Brien at the close of one late shift. "I have to believe O'Brien aced his verbal SATs," Kalbacker reports. "He's quite, well, verbal. And he immediately invited me to return for another conversation with the line, 'I love to babble.' "

1.

[Q] Playboy: You're the son of a physician and an attorney. Is hosting a late-night television show an attempt to escape a destiny in medicine or law?

[A] O'Brien: This show is an attempt to say to my parents, "For God's sake, help me." I realized early on that I didn't want to be a doctor like my father or a lawyer like my mother. There had to be something else for me. I seized on game-show host. Everyone has a hero, and for me it's Wink Martindale. I thought, What better thing for me to do than to be able to comb my hair into a pompadour and give away cash prizes? When this Late Night thing came along, I thought, I'll grab it and maybe, over time and with a little luck, it will transform into a game show. We're getting there. Andy and I are starting to develop that cheesy patter. Insincerity levels are rising rapidly, and around 1998--God willing--America will tune in and see a Toyota Camry slowly revolving in the background, and people will be bobbing for apples and cheering wildly. Then we'll really have something.

2.

[Q] Playboy: Your show debuted the day Yitzhak Rabin and Yasir Arafat shook hands. We recall your remark, "Conan O'Brien will get a talk show when there's peace in the Middle East," but we find no mention of your name in diplomatic exchanges. Can we assume it was a coincidence?

[A] O'Brien: It all came together nicely, and I feel the show was influential. Monday, September 13, 1993. The night I premiered, the picture appeared of Clinton with Rabin and Arafat shaking hands on the White House lawn. I had advance knowledge. We don't read newspapers just to come up with the monolog jokes. A good 40 percent of the writers on this show are former Israeli commandos. They rush in at the last second and say, "Madonna's having a baby!" I ask if they're sure. "Yes, we lost two men finding out."

3.

[Q] Playboy: Saturday Night Live impresario Lorne Michaels was assigned by NBC to come up with a replacement for David Letterman. Explain how he tapped you for the job.

[A] O'Brien: I'm not at liberty to go into that because it would diminish what I've achieved. But let's just say that Lorne had to choose me at that point in his life, and I hope to become very wealthy off some land deals. God bless him. I'm sure I owe the guy a lot. He didn't have the power to actually say, "Conan O'Brien is going to replace David Letterman." The crucial role that he played was in telling NBC, "There's this Conan O'Brien guy who will be green at first, but he's smart and has some talent and I think you should check him out." Then there was an audition on the Tonight Show set and some meetings with NBC where I talked about what I'd do with the show: "This will show them. This is going to knock Silk Stalkings off the air."

4.

[Q] Playboy: You've had long-term experience with short-term employment. How did you deal with the lack of job security, which affects so many Americans today?

[A] O'Brien: During the first year and a half of the show's run we were renewed every 40 minutes. I bought one of those digital watches with an alarm, and it was pretty much chiming all the time. Now I look back fondly on those early rough times. My first professional job in Los Angeles, in 1985, was with Not Necessarily the News on HBO. I was on a three-week contract because they didn't know if I was funny. I checked into the Oakwood Apartments, which is kind of halfway between an apartment building and a hotel. It's a great place to meet single, pregnant women, because a lot of them go there when they break up with their husbands, and they ask if you want to go out for dinner. In the middle of my second week I found out that I was getting picked up for 13 weeks more, and then after that I was getting picked up for 26. Here I have my own TV show and I'm 30 years old, and in my gut I just don't feel I have anything to complain about. If I'd started bitching about getting only a 13-week television contract, America would have had the right to kick me in the ass.

5.

[Q] Playboy: Early in your Late Night run critics knocked you as being a frat boy. Do you consider that criticism unfair given that your alma mater, Harvard, is famous for other types of exclusive societies?

[A] O'Brien: There are a ton of them, none of which I was invited to join. Porcellian is the most exclusive. It turned down Franklin Roosevelt. A lot of people theorize that the New Deal was FDR's revenge against Porcellian for not letting him in. I was never one who would have joined a frat. I don't like to high-five people, and I'm not the kind of guy who likes to bump chests with anybody. Mine would collapse. I have a high, weak sternum that's calcium deficient. Andy's not really a frat guy, either. But people need quick labels for you. I never waste time trying to figure out what's fair or unfair. Critics who didn't like the show at first, most notably Tom Shales [of The Washington Post], have since said they really like it. There's been a terrible mistake, and I'm just going to keep my mouth shut and try to benefit from it.

6.

[Q] Playboy: Television executives are not known for their patience. Why weren't you canceled after just a couple of months?

[A] O'Brien: They forgot I was on the air. They may even have told somebody, "Go cancel that guy," but he didn't know how to get in touch with me. By the time he figured it out, we were doing better. The serious answer is that we were probably staying barely ahead of the machine that cancels you. Our ratings never dipped that low. I don't even want to know how close we came in the first six months. When you're in great danger, it's good you never actually have time to think about how much trouble you're in.

7.

[Q] Playboy: You recently moved to a new Manhattan apartment. Did your first year-long NBC contract make you more comfortable about investing in real estate?

[A] O'Brien: Things are going much better on the show now, but I haven't gotten crazy. I didn't buy an apartment. I'm still renting. I'm not a fool. I looked into buying an apartment in New York, but the process scared the hell out of me. They say, "If you want this small apartment, you can pay $2 million for it, and after you agree to do that, we'll consider whether or not we're going to let you have it." You almost faint dead away. You don't get a park view, and then they tell you Bruce Willis and Demi Moore just bought the penthouse for $15 million, and they bought it to keep their tennis shoes in. I bought a small house in Connecticut. It's not an estate. I was hoping that if I bought the house in Connecticut, then I'd get the stalker. And then maybe I'd finally live up to Dave's legend. But it didn't happen.

8.

[Q] Playboy: We understand you're the lowest-paid late-night host, pulling down about $2 million a year. Won't you be looking to up the ante when your contract comes up for renewal?

[A] O'Brien: "I think I'm still the lowest paid," he said with obvious pride. I don't get into specifics, but it's around there. I'm doing really well compared with the rest of my family. Compared with the 11:30 guys, I'm thrilled with how much money I make. It sounds like a cliché, but I don't get obsessed with money. Doing these shows is fun when it goes well, and that's the addictive part. Later on so much of this business is "How much do you earn?"--meaning the respect you're being shown by the industry. Maybe I have low self-esteem. I'm happy that people know who I am now. They actually make eye contact with me. I'm euphoric that NBC runs promos for my show. It'll be years and years before I make outrageous demands--like renaming NBC the Conan Channel.

9.

[Q] Playboy: The evidence indicates that Harvard graduates are represented in disproportionately large numbers in the comedy-writing business. Should we be concerned?

[A] O'Brien: Yes. Look what happened when Harvard people took over running the Vietnam war. You know it has gone too far when they introduce napalm and chemical defoliants in the prime-time schedule. There have been mentions of it here and there, but I'm waiting for the big whistle-blowing article that says, "Hey, wait a minute. How come all these assholes get to have TV jobs?" The government will step in, the way it broke up AT&T. For some Harvard people, being a TV writer is what being a stockbroker was in the Forties and Fifties. It's socially acceptable now to graduate from Harvard and do a season on Roseanne, which is absurd because the show is about a lower-middle-class woman in the Midwest and deals with the stuff real people have to deal with. You have this image of a guy who wrote his thesis on Nietzsche trying to figure out whether or not Dan should buy a trailer park.

10.

[Q] Playboy: Tell us a tale of young Conan O'Brien, Harvard student.

[A] O'Brien: I majored in American history and literature and, boy, have I put that to good use. I wrote a thesis on William Faulkner and Flannery O'Connor and all the things I have been trying to work into the show. Harvard is deeply ashamed of me. If you write a thesis at Harvard, you, too, can interact with a gaseous wiener. I have mixed feelings about my Harvard past. I don't want to completely trash it because I worked hard to go there. I wasn't a legacy. I wanted to make, something of myself, and I was proud to get into Harvard. Then I got into comedy and they made me president of the Lampoon. I got to edit the magazine for two years in a row, and that was unusual. After college I didn't limit my circle to the Harvard writing community. I made an effort to become friends with performers from different parts of the country who had never heard of the Lampoon. I was getting up on that stage in Chicago wearing a diaper. I used to do a bit called Kennedy Baby, where I played a giant baby who talked like Ted Kennedy, and I would do it in a diaper. To people who say I haven't paid my dues, I've paid my dues. I have pictures to prove it.

11.

[Q] Playboy: Did you feel more secure in the role of host after visits from such late-night regulars as Tony Randall and Dr. Joyce Brothers?

[A] O'Brien: Definitely. We have even had nights when Ed McMahon has come by and chuckled at things. I knew we had a real talk show the night I said, "Ladies and gentlemen, put your hands together for Charo." She came on and shook her tits and said, "Cootchie-cootchie." She'd say things I wouldn't understand, and I would do Carson takes to my camera. I really get excited in those moments because I feel like I've paid for a virtual reality ride: If you're at least this tall and not pregnant and you don't have a pacemaker, you can strap yourself in and make quips and Ed McMahon will sit next to you and guffaw.

12.

[Q] Playboy: Do you pay royalties to the creators of Clutch Cargo, who came up with the idea of putting moving lips on cartoon faces? And have you taken legal steps to protect your own intellectual property?

[A] O'Brien: No, we don't pay royalties, and this interview is over. My God, I don't think anybody would want any of our intellectual property. That's our great security blanket. Letterman actually had comedy bits that people would want to take, but I decided early on that I wasn't going to run into this whole intellectual-property thing. So we create comedy that no one would ever dare touch, and it's worked beautifully. No one rips us off. None of our impressions are accurate. They're incredibly insane and overblown and (continued on page 162)Conan O'Brien(continued from page 114) cartoonish, and people like that. We have a Bob Dole who sounds like the mayor of Munchkin Land. We have a Clinton who sounds like Slim Pickens' character in Dr. Strangelove. We have a Boris Yeltsin who is Boris Badenov of Rocky and Bullwinkle fame. We put these lips on them and people just accept it.

13.

[Q] Playboy: We've noticed you've become much more comfortable with the talk-show host's tradition of interrupting guests to make jokes at their expense.

[A] O'Brien: I usually interrupt them to make jokes at my expense. My style isn't so much to destroy people. I'd do it if I could. If I could rip people apart verbally and leave them smoldering, I'd do it. If there's someone on the show who has to be ridiculed, like Fabio, I'll do the job. But I don't usually see that as my goal. I'll just be the fast-talking, half wise guy--half coward who makes guests act more foolish than they normally would by acting foolish myself. I don't really think I'm a horrible freak, but it's always been a source of my comedy. I've had people say to me, "The show's doing great now, so you should stop doing self-deprecating humor." They don't understand. If the show knocked 60 Minutes and Friends off the chart and became this entertainment juggernaut, I'd still find myself fairly ridiculous. When attractive women come on, I flirt with them. I generally make a fool of myself, but that means all the men watching at home can feel better about themselves because they know they would have handled it better. They choose me for late night so they can feel better about themselves.

14.

[Q] Playboy: Do you predict a talent-search program and magazine publishers' prize giveaways in Andy Richter's future?

[A] O'Brien: Ed McMahon and Andy have already entered into discussions. It's really up to Ed who will be the chosen sidekick for the next generation. On our show, there was no goal to revive the sidekick. The only goal was to go back to more of a Carson treatment--to revisit that era of TV talk shows with full-blown sketches and production numbers. What Letterman did so brilliantly was to create the comedy of not trying. I couldn't out-Letterman Letterman. I couldn't take ironic detachment to the next level. I kept hearing the name Andy Richter, so I set up a meeting with him. I was ten minutes into talking with him and I thought, I'm going to hire this guy. What's great about Andy is he has that solid Ed McMahon look and a deep announcer's voice, and he has a little bit of the polish a second banana should have.

15.

[Q] Playboy: The clip of a guest's latest movie is standard late-night fare. Do you feel terribly used when guests plug their projects, or are you grateful for anything that helps fill airtime?

[A] O'Brien: I choose B. So they show a clip, great. That's 30 seconds I don't have to think about. These shows are whorehouses. People come on and pretty much prostitute themselves for their projects, and I prostitute myself for their projects. I do an hour a night, and if someone came on and wanted to show a 40-minute clip, I'd shake his hand and say, "Go ahead, I don't care." During clips, I leave the stage, get a massage and talk with my family in Boston.

16.

[Q] Playboy: You're an M.D.'s son, so we presume you take a special interest in your employees' medical care. Have you enrolled Late Night staffers in an HMO, or do you allow them to choose their own physicians?

[A] O'Brien: I'm the Henry Ford of late-night talk shows. I'm for getting the cheapest labor possible and providing the fewest services. I'm very backward in my views. I'll provide leeches if you get sick. But I'm one of those people who lets everything get better on its own. So was my dad, who would say if I had a sore throat, "Your immune system will take care of it and you'll get better."

17.

[Q] Playboy: Fashion style is evolving from grunge and stubble to the clean-cut look with a healthy shock of hair. Want to claim some credit?

[A] O'Brien: Yes. But the master is really Jack Lord of Hawaii Five-O. Nobody has ever had cooler hair than Jack Lord. If they don't broadcast Hawaii Five-O in your area, call your cable company and ask for it. That guy had the hair. Some people think I started having crazy hair when I got my TV show. Not true. In high school I looked like Jack Lord. I was working on the Jack Lord thing when I was, like, 16 years old. I don't know why I had that obsession, but I wanted my hair to be a shelf that I could keep figurines on.

18.

[Q] Playboy: One night you showed a tape of a White House dinner you attended in honor of Irish president Mary Robinson. Wasn't that instance of self-promotion just a bit too blatant?

[A] O'Brien: There's this old saying that the reason American Plains Indians--Native Americans; I want to be politically correct here--were able to survive was that they used every part of the buffalo. They didn't just use the meat, they also used the foreskin to make coin pouches and used the hooves as telephones. This show uses every part of the buffalo. If something happens in my private life or in Andy's private life, we turn it into a comedy sketch. When the White House invites me to a state dinner because it's rounding up "prominent Irish Americans"--isn't that a great phrase?--and there's footage of me shaking hands with the president, we're going to turn it into a comedy bit. For this, by the way, they invited every Irish American who had a job to the White House, and those who wore tuxes were allowed in the door. The White House has it down like a good restaurant. The maître d' comes by and shakes your hand and knows who you are and says, "So good to see you, right this way." We got real good Irish cuisine: beef marbled with lots of fat and a potato and then another potato and then for dessert, a potato. The weirdest part of the evening was when dessert came: It had a chocolate Irish flag on top. I thought it was such a strange act of patriotism to eat your native country's flag, but I did it happily.

19.

[Q] Playboy: You recently visited the Emerald Isle. Was it only your great height that set you apart from the locals?

[A] O'Brien: Visiting Ireland for the first time was very much like waiting to use the bathroom in my family's house, hanging around with people who have big, wide faces and pleasant dispositions. Suddenly it all made sense. Going back to Ireland, I understood why my skin is so pale. It's really foggy and rainy there. And I understood why I talk so much, because everyone was very inquisitive and talkative. I saw why my cholesterol is so high. Want some more butter? How about more meat? Want some sausage? Have some butter with that meat. Some more meat with your sausage? Gravy with that? So many things hooked up for me, it was a revelation. So this is why I am the way I am. This is why I'm destined to have a heart attack when I'm 48.

Something most people don't know about the Irish is that our heads are twice the size of other people's heads. We have giant heads and big faces. Look at Ted Kennedy's head in your spare time. That guy's got a giant melon. And Daniel Patrick Moynihan. That's the curse of the Irish--giant heads, balloon heads, parade-float heads. Irish people can have normal-sized heads into their 30s, but once they get into their 40s, their faces get really big and red and round. It's going to happen to me. I'll have to get out of TV for that reason.

20.

[Q] Playboy: You and your girlfriend spent a New Year's Eve together with your ex-girlfriend, Friends star Lisa Kudrow, and her husband. Are you trying to show the rest of us how to manage our relationships with women in a sophisticated, mature way?

[A] O'Brien: I hope so. That's the point of it all. The reason it works is that Lisa and I were really good friends for 98 percent of the time we knew each other. I know you're not interested in that, but we created a foundation that helped us survive the fact that we were involved and then we weren't. Would you like to hear that we spent the evening in a chalet? I can make it a chalet if you want. All right, it was in a chalet. Lisa's husband and I came to blows. We fought in the snow. Lisa came out and said, "Stop it, I won't have it anymore." Just then lightning struck. We realized we had been making fools of ourselves, apologized and walked all the way back to town as the snow fell. How do you like that? Want the truth? We had a really good time. We went to a restaurant. The part I didn't like about the evening was that they provided silly hats. I'm just not a silly-hat guy, not because I might make a fool of myself but because it obscures valuable hair. But Lisa and her husband and my girlfriend all put on the silly hats, so eventually I had to.

the hair-enhanced talk-show host cracks wise about his alma mater, his brush with tv death and his treatment for a sore throat

Nobody has cooler hair than Jack Lord. I wanted my hair to be a shelf that I could keep figurines on.