Playboy: How bad were your early days on the show?
O'Brien: Bad. Dave left here under a cloud; his fans and the media were angry with NBC. Then NBC picks a guy with crazy hair and a weird name. From Harvard. And the world says, "Harvard? Those guys are assholes." I sincerely hope that the winter of December 1993, our first winter, was the worst time I will ever have. I'd go out to do the warm-up and the back two rows of seats would be empty. That's hard to look at. I would tell a joke and then hear someone whisper, "Who's he? Where's Dave?"
Playboy: You had trouble getting guests.
O'Brien: Bob Denver canceled on us. We shot a test show featuring Al Lewis of The Munsters. We did the Clutch Cargo thing with a photo of Herman Munster. Unfortunately Fred Gwynne, who played Herman, had recently died, and Al Lewis kept pointing at the screen, saying, "You're dead! I was at your funeral!"
Playboy: For months you got worried notes from network executives. What did they say?
O'Brien: They were worried. The fact that Lorne Michaels was involved bought me some time. But Lorne had turned to me at the start and said, "OK, Conan. What do you want to do?" Now television critics were after me and the network was starting to realize what a risk I was. Suggestions came fast and furious. I kept the note that said, "Why don't you die?"
Playboy: Did they suggest ways to be funnier?
O'Brien: They were more specific and tactical. The network gets very specific data. Say there was a drop in the ratings between 12:44 and 12:48 when I was talking to Jon Bon Jovi. I'll be told, "Don't ever talk to him again." Or they'll want me to tease viewers into staying with us: "You should tease that -- say, 'We'll have nudity coming up next!'"
Playboy: You did come close to being canceled.
O'Brien: We were canceled.
Playboy: Really? You have never admitted that.
O'Brien: This is the first time I've talked about it. When I had been on about a year, there was a meeting at the network. They decided to cancel my show. They said, "It's canceled." Next day they realized they had nothing else to put in the 12:30 slot, so we got a reprieve.
Playboy: Were you worried sick?
O'Brien: I went into denial. I tried hard not to think, Yes, I'm bad on the air and my show has none of the things a TV show needs to survive. We had no ratings. No critics in our corner. Advertisers didn't like us. Affiliates wanted to drop us. Sometimes I'd meet a programming director from a local station where we had no rating at all. The guy would show me a printout with no number for Late Night's rating, just a hash mark or pound sign. I didn't dare think about that when I went out to do the show.
Playboy: Are you defending denial?
O'Brien: How else does anyone get through a terrible experience? The odds were against me. Rationally, I didn't have much chance. Denial was my only friend. When I look back on the first year, it's like a scene from an old war movie: Ordinary guy gets thrown into combat, somehow beats impossible odds, staggers to safety. His buddy says, "You could have been killed!" The guy stops and thinks. "Could have been killed?" he says. His eyes cross and he faints.
Playboy: How did you dodge the bullet?
O'Brien: There were people at NBC who stood up for me. I will always be indebted to [NBC West Coast president] Don Ohlmeyer, who stuck to his guns. Don said, "We chose this guy. We should stick with him unless we get a better plan." He was brutally honest. He came to me and said, "Give me about a 15 percent bump in the ratings and you'll stay on the air. If not, we're going to move on."
Playboy: Ohlmeyer started his career in the sports division.
O'Brien: Exactly. His take was, "You're on our team." Of course it wasn't exactly rational of Don to hope I'd be 15 percent funnier. It was like telling a farmer, "It better rain this week or we'll take your farm."
Playboy: What did you say to Ohlmeyer?
O'Brien: There wasn't time. I had to go out and do a monolog. But I will always be indebted to Don because he told me the truth. Wait a minute -- you have somehow tricked me into talking lovingly about an NBC executive. Let me say that there were others who were beneath contempt -- executives who wouldn't know a good show if it swam up their asses and lit a campfire.
Playboy: Finally the ratings went your way. Hard work rewarded?
O'Brien: Well, I also paid off the Nielsen people. That was $140,000 well spent.
Playboy: Ohlmeyer plus bribery saved you?
O'Brien: There was something else. Just when everyone was kicking the crap out of the show, Letterman defended me.
Playboy: Letterman had signed off on NBC saying, "I don't really know Conan O'Brien, but I hear he killed someone."
O'Brien: Then I pick up the paper and he's saying he thinks I'm going to make it. "They do some interesting, innovative stuff over there," he says. "I think Conan will prevail." And then he came on my show as a guest. Remember, this was when we were at our nadir. There was no Machiavellian reason for David Letterman, who at the time was the biggest thing in show business, to be on my show.
Playboy: Why did he do it?
O'Brien: I'm still not sure. Maybe out of a sense of honor. Fair play. And it woke me up. It made me think, Hey, we have a real fucking television show here. Of six or seven pivotal points in my short history here, that was the first and maybe the biggest. I wouldn't be sitting here -- I probably wouldn't exist today -- if he hadn't done our show.
Playboy: The Late Night wars were hardly noted for friendly gestures.
O'Brien: How little you understand. Jay, Dave and I pal around all the time. We often ride a bicycle built for three up to the country. "Nice job with Fran Drescher!" "Thanks, pal. You weren't so bad with John Tesh." We sleep in triple-decker bunk beds and snore in unison like the Three Stooges.
Playboy: You talk more about Letterman than about your NBC teammate Leno.
O'Brien: I hate the "Leno or Letterman, who's better?" question. I can tell you that Jay has been great to me. He calls me occasionally.
Playboy: To say what?
O'Brien: [Doing Leno's voice] "Hey, liked that bit you did last night." Or he'll say he saw we got a good rating. I call him at work, too. It can be a strange conversation because we're so different. Jay, for instance, really loves cars. He's got antique cars with kerosene lanterns, cars that run on peat moss. He'll be telling me about some classic car he has, made entirely of brass and leather, and I'll say, "Yeah man, I got the Taurus with the vinyl." One thing we have in common is bad guests. There are certain actors, celebrities with nothing to say, who move through the talk show world wreaking havoc. They lay waste to Dave's town and Jay's town, then head my way.
Playboy: You must be getting some good guests. Your ratings have shown a marked improvement.
O'Brien: Remember, when you're on at 12:30 the Nielsens are based on 80 people. My ratings drop if one person has a head cold and goes to bed early.
Playboy: Actually you're seen by about 3 million people a night. Your ratings would be even higher if college dorms weren't excluded from the Nielsens. How many points does that costs you?
O'Brien: I told you I'm an idiot. Now I have to do math, too?
Playboy: Do you still get suggestions from NBC executives?
O'Brien: Not as many. The number of notes you get is inversely proportional to your ratings.
Playboy: What keeps you motivated?
O'Brien: Superstition. We have a stagehand, Bobby Bowman, who holds up the curtain when I run out for the monolog. He is the last person I see before the show starts, and I have to make him laugh before I go out. It started with mild jabs: "Bobby, you're drunk again." Bobby laughs, hee-hee. Then it was, "Still having trouble with the wife, Bobby?" But after hundreds of shows you find yourself running out of lines. It's gotten to where I do crass things at the last second. I'll put his hand on my ass and yell, "You fucking pervert!" Or drop to my knees and say, "Come on, Bobby, I'll give you a blow job!" "Ha-ha. Conan, you're crazy," he says. But even that stuff wears off. Soon I'll be making the writers work late to give me new jokes for Bobby.
Playboy: Did you plan to be a talk show host or did you fall into the job?
O'Brien: I was an Irish Catholic kid from St. Ignatius parish in Brookline, outside Boston. And that meant: Don't call attention to yourself. Don't ask for too much when the pie comes around. Don't get a girl pregnant and fuck up your life.
Playboy: Were you an altar boy?
O'Brien: I wanted to be an altar boy, but the priest at St. Ignatius said, "No, no. You're good on your feet, kid," and made me a lector. A scripture reader at Mass. He was the one who spotted my talent.
Playboy: What did you think of sex in those days?
O'Brien: I was sexually repressed. At 16 I still thought human reproduction was by mitosis.
Playboy: How did you get over your sexual repression?
O'Brien: Who says I got over it? My leg has been jiggling this whole time.
Playboy: What were you like in high school?
O'Brien: Like a crane galumphing down the hall. A crane with weird hair, bad skin and Clearasil. Big enough for basketball but lousy at it. My older brothers were better. I would compensate by running around the court doing comedy, saying, "Look out, this player has a drug addiction. He's incredibly egotistical." I was an asshole at home, too. My little brother Justin loved playing cops and robbers, but I kept tying him up with bureaucratic bullshit. When he'd catch me I'd say, "I get to call my lawyer." Then it was, "OK, Justin, we're at trial and you've been charged with illegal arrest. Fill out these forms in triplicate." Justin was eight; he hated all the lawsuits and countersuits. He just cried.
Playboy: Were you a class clown?
O'Brien: Never. I was never someone who walked into a room full of strangers and started telling jokes. You had to get to know me before I could make you laugh. The same thing happened with Late Night. I needed time to get the right rhythm with Andy and Max and the audience.
Playboy: So how did you finally learn about sex?
O'Brien: My parents gave me a book, but it was useless. At the crucial moment, all it showed was a man and a woman with the bedcovers pulled up to their chins. I tried to find out more from friends, but it didn't help. One childhood friend told me it was like parking a car in a garage. I kept worrying about poisonous fumes. What if fumes build up? Should you shut off the engine?
Playboy: For all your talk of being repressed, you can be rowdy on the air.
O'Brien: The show is my escape valve. When I tear off my shirt and gyrate my pelvis like Robert Plant, feigning an orgasm into the microphone, that shows how repressed I am -- a guy who wants to push his sex at the lens but can only do it as a joke.