Hangin' 10: On his anniversary, CONAN O'BRIEN recounts how he rode the wave from laughingstock to late night's foremost lunatic in one decade flat By Dan Snierson; Conan O'Brien -- Entertainment Weekly -- September 12, 2003 A hot, drizzly night. August. Rockefeller Center. Passersby jam up against security barricades, trying to sneak a peek as Conan O'Brien tapes promos for the 10th-anniversary celebration of his late-night talk show on NBC. After zinging the lens with prepared one-liners--"When I started, they said I wasn't going to last six months. Ha! Stupid doctors!"--he scribbles autographs, nods at shout-outs from fans, and is shepherded away by his staff, whom he mock-abuses. (To one: "Don't speak to me directly." To another: "You're fired." To another: "Take his job.") Safely ensconced in an Italian restaurant a few minutes later, he reflects poignantly on the hubbub. "Whenever there's a lot of people staring at me, I'm always thinking 'Here comes the gun,'" he says. "If I start thinking 'We've finally made it!' a guy would leap out of the crowd with a thick wax mustache and say, 'Now Carson Daly is 12:30!'" Assuming an anchorman's stentorian voice, he continues: "He fired four shots. Conan slumped quietly to the floor. His last words were 'Tell the Masturbating Bear I love him.'" With that, the 40-year-old host turns straight-faced. "Never say we finally made it. Never say it." Okay, how about this: The man once saddled with limp ratings, pin-drop buzz, and daily threats of cancellation now anchors one of the most revered, inventive comedy hours on television. Don't believe us? After scoring eight Emmy nominations for writing, Late Night just received its first Outstanding Variety, Music or Comedy Series nod. Still don't believe us? Maybe David Letterman can convince you: "In the world of television, 10 years is a true accomplishment. Conan deserves all the credit in the world." As Late Night With Conan O'Brien prepares to ring in the milestone with a 90-minute prime-time special on Sept. 14, we asked Conan & Co. to reflect on a decade of deliriousness. "The last 10 years have been like a Bataan Death March that ended at a Dairy Queen," notes O'Brien. "Long, arduous, difficult--but ultimately happy and refreshing." I. A LONG SHOT'S JOURNEY INTO NIGHT "The perfect world would be where The Conan O'Brien Show would be on, and you'd be reading my short story somewhere and wearing my designer jeans," O'Brien told The Harvard Crimson upon graduating in 1985. Designer dreams were soon crushed, though, and he pursued comedy. He applied to write for Late Night With David Letterman in 1987--but was rejected. Eventually, O'Brien got a writing gig with Saturday Night Live, then joined The Simpsons. In 1993, Letterman bolted for CBS, leaving NBC desperate for a 12:30 a.m. replacement. RICK LUDWIN (NBC SENIOR VP, LATE NIGHT): Whoever was going to get this job was going to be somebody who frankly had nothing to lose. If you took that job and failed, you were likely to be through in show business. NBC enlisted SNL creator Lorne Michaels to oversee the show. After O'Brien passed on producing the new Late Night, Michaels offered him a crack at the hosting chair. An audition went down on the Tonight Show set in Burbank. LUDWIN: He looked like he just fell out of bed at his fraternity house. [But] the wit was there from day one. CONAN O'BRIEN: I was much better at my audition than I was for the first year of my show. Meanwhile, Garry Shandling took himself out of contention. In April 1993, O'Brien was announced as the new host of Late Night. O'BRIEN: When I got the call, I wasn't, "Yeehaw! Let's go have some champagne!" I was, "Okay, time to suffer." Part of me in a sick way liked the idea: "I'm going to go get the s---kicked out of me for two years and I'm going to be mocked and ridiculed but slowly over time, the show's going to get better and better." It's like a Catholic masturbatory fantasy. LORNE MICHAELS: I said, "It's a 12-round fight in which you're going to get pounded for the first eight rounds. And if you're still standing after the eighth round, people will go, 'You know, I like that guy.'" I wanted him as mentally prepared as possible for the pounding. Whoa, was the pounding worse. The gamble was on. Studio 6A, Letterman's old home, was gutted. Robert Smigel, an SNL scribe and O'Brien pal, was tapped as head writer; Bruce Springsteen's drummer, Max Weinberg, was hired as bandleader. And O'Brien met with actor-writer Andy Richter at an L.A. deli. O'BRIEN: It was a really hot day. I got a Coke, and Andy said, "I'll have the borscht." And they brought this big bowl of borscht, which looked like blood. Within 45 seconds, I was thinking "I love this guy and I want him on the show. We'll figure out what he does later on." ANDY RICHTER: It's a deli. That's what you do there. You eat deli food. You don't just drink a Coke. That's what's weird. Late Night With Conan O'Brien debuted on Sept. 13, 1993; in the first few weeks, signature bits like In the Year 2000, Clutch Cargo, and If They Mated were launched. O'BRIEN: The first week felt really good. Then Chevy Chase got canceled. I just had this bad feeling. People were so angry about The Chevy Chase Show, but once they killed it, I think they felt like, "Serve up the next one." I was the guy tiptoeing out of the room, and they're like, "You! Get back here!" That's when the s---hit the fan. ROBERT SMIGEL: We were getting bad reviews fairly quickly, but at the same time I was getting congratulatory phone calls from people in comedy. George Meyer, legendary Simpsons writer, calls and he's like, "Amazing. You guys figured out how to replace Letterman. It's completely original and funny." And at the same time we're hearing "This is a disaster." O'BRIEN: The most compelling TV we ever did was the first year because we were trying stuff that was like, "Oh, my God, they shouldn't have tried that." We had a bird that came down halfway through Mary Tyler Moore's charming story and it goes [makes squawking noise], and I'd say, "You just said the secret word!" and we startled her. You can't drop a bird on Mary Tyler Moore's head halfway through an interview. The show's ratings were lackluster (averaging 2 million viewers the first year); reviews were even worse. (Washington Post critic Tom Shales called Late Night "roadkill.") Audience seats had to be filled out by NBC interns. JEFF ROSS (EXECUTIVE PRODUCER): We're getting all these notes from the network. Every day. On and on with notes. His hair, what he was wearing, they didn't like the comedy.... LUDWIN: He was giggling too much. It was a nervous tic. SMIGEL: He was Conan everywhere but on camera. RICHTER: One guy told Conan what he needed to do was get up in the audience and run around. Like that's the silver bullet. O'BRIEN: [Then--NBC Entertainment president] Warren Littlefield told me "You have to fire Andy Richter." RICHTER: I wasn't aware of them trying to do that. I was just "the other one" and they didn't need to talk to me. WARREN LITTLEFIELD: Early on, those two guys were awkward together. We wondered if having Andy was holding back Conan's growth. Conan felt strongly that Andy was a critical part of the mix. SMIGEL: It did make things more challenging for Conan that we picked a guy who's actually funny. It might be easier for him if he had a doormat so he wouldn't have to worry about making room for Andy to get in his lines. O'BRIEN: I told [Littlefield], "I'm working on a different role for Andy." And Andy kept being there and being there. And to his credit, when it was clear that Andy was hilarious, he called me up and said, "I was wrong about Andy." Soon the issue was bigger than saving Andy, as NBC's Ludwin found himself battling disenchanted colleagues. One ominous sign: Up-and-comer Greg Kinnear was hired to anchor NBC's Later at 1:30 a.m. O'BRIEN: It was very clear why he was being brought in. Like, "This robot's malfunctioning. What are you guys working on over there?" "The RXK-55 series. It has twice as many transistors as yours." LUDWIN: There was a meeting in Burbank [in 1994]. And that meeting ended with the books being closed--we're going to cancel the show. We're going to move Kinnear to 12:30. And then the books got reopened--we discussed it more and it was decided, "All right, we won't do it yet." I did feel like The Last of the Mohicans. O'BRIEN: Rick could see what a lot of people couldn't, which was that the audience was laughing. After its near-cancellation experience, Late Night held on tenuously. In 1994, O'Brien was supposed to receive a one-year extension. Instead, he was offered week-to-week pickups. (Producers held out for 13-week extensions, which they got.) Meanwhile, O'Brien worked the phones, calling dozens of disgruntled affiliates for damage control. O'BRIEN: It was like "Okay, for an hour every day after the show, I'm going to soak a long stick in acid and then ram it up my ass." That's how it felt. I would go, "Hello? Are you the station manager? Hi, Conan O'Brien calling." Long pause. They just hated me. I went to one affiliate thing in Florida and I walked up to one guy and put out my hand and he wouldn't shake it. RICHTER: At our first Christmas party, [Conan] got drunk and commandeered the band and made them play these Eddie Cochran songs three times in a row. It kind of got weird and awkward. It was sort of like Valley of the Dolls. "You're all gonna look at me now!"... Once, some network guy, after a really tough show that really went well, insulted him and told him it was terrible. He got so mad that he just had to throw up. O'BRIEN: People can say Wow, you suck at sports, or your hair is weird, but if someone says you're not funny, that's the thing that would hurt me the most. For a year there, it looked like I could become famous as one of the most unfunny people ever, and that was the nightmare. I was in a sinking car that was going to the bottom of the ocean and I was getting out of that car. I was not going to become famous for being unfunny. I'll cudgel America into accepting me. II. TURNAROUND IS FAIR PLAY Ever so slowly, sentiment began to shift. David Letterman's 1994 appearance was the first sign of life. Growing ratings for The Tonight Show helped lift Late Night's numbers, and A-listers stopped ducking booking requests. In 1995, Shales--in a huge about-face--declared O'Brien "one of the greatest examples of a self-makeover in television history." O'BRIEN: There was no one turnaround, there were 45. But you needed each one to turn the whole battleship around. MICHAELS :The real thing was just getting him to the point where he looked like he belonged on television. And that took what it was always going to take--a year. SMIGEL: I'm not sure the show would have made it if Letterman hadn't done it. It meant a lot for the morale, and it had some sort of effect on the press and possibly the network. O'BRIEN: We made it to the first summer and that's when all these kids who'd been watching us in their dorms came [to see the show]. Suddenly, people are standing in the aisles. O'Brien gained even more momentum in April 1995 when he hosted the White House Correspondents' Dinner. O'BRIEN: It's a tough, tough room and I just started killing. Clinton was pounding the table and his face was red and he was crying. The next day I felt like I had taken a backpack off. 6A seemed smaller and more manageable. LITTLEFIELD: Seabiscuit. Complete and total underdog. In entertainment, I'm hard-pressed to come up with a greater turnaround. In 1997, having earned NBC's support and a 25 percent ratings increase from the first year, O'Brien inked a slightly longer contract: five years. "That's when I felt I had battled my way back completely," he says. Things were finally running smoothly--then Richter gave notice in February 1999 he was leaving the following year. RICHTER: I set out to be an actor. I never wanted to be a broadcast personality. Early on, I realized at some point I was going to have to jump off. I think also my attention deficit disorder is too strong. It was a combination of plain old entrepreneurial spirit and itchiness. O'BRIEN: I just knew there's no talking somebody out of something like that. ROSS: It was probably the last network note we've gotten, which was, Who are you going to get to replace him? You should get a woman, you should get a black person. Conan and I talked about it at length and realized that Andy was not created out of a search for a sidekick. We decided unless something organically happens, we'll do without one. O'BRIEN: I really think people didn't want to see someone sitting in Andy's chair and doing Staring Contests with me right away. And I don't feel like we need to arbitrarily have someone here now. III. BIT BY BIT Late Night has birthed some of TV's most bizarre characters and comedy bits, such as Pimpbot 5000 (half '50s robot, half '70s street pimp), Staring Contest (Conan silently squaring off with Andy while distracting him with random acts of absurdity), and the ridiculous prophecies of In the Year 2000 ("In the year 2000, apes will ride on horseback and horses will ride apeback.") Some other classics: The self-explanatory Masturbating Bear, which was a jab at affiliates that had complained that the show was too dirty. O'BRIEN: The thing that's funny to me is that he's wearing a diaper and he's also not crudely masturbating--he's batting at his genitalia frantically, which makes it acceptable to [network] standards. LUDWIN: I remember saying "Can't we call that character 'The Bear That Likes to Pleasure Himself'?" MIKE SWEENEY (HEAD WRITER): If we write other sketches with bears, the second a bear appears, the crowd gets really excited and then they see it's just a regular, non-masturbating bear and they're like, "Ahh, we got screwed." Triumph the Insult Comic Dog (voiced by Smigel) debuted Feb. 13, 1997, mercilessly mocking everything in his path: celebrities, Star Wars geeks, the Westminster dog show... O'BRIEN: There's something anarchic about it. You see a dog puppet with a cigar tormenting people holding lightsabers and dressed as Darth Vader and you think: How did we come to this? SMIGEL: There've been times where I didn't have the balls to say anything to a celebrity's face, so I mouthed Triumph and put a line in later. I was not going to say "I've got chew toys that look better than you" to Mick Jagger. Puff Daddy--the line was like "Hey, Puffy, don't you remember me? We rode together in your limo once, you stuffed a gun up my ass to hide it from the cops." IV. GUEST RELATIONS O'BRIEN: There's part of me that just refuses to have a bad interview. That might just be an extension of my horrible neediness as a performer. I'll stand on my head, I'll get on the desk. It doesn't mean it always works. I just keep trying. That can be sad to watch. Left-winger Alec Baldwin turned his December 1998 appearance into a federal issue.... O'BRIEN: He was going to be ranting about the damn Republicans and we were going to put on an oxygen mask to calm him down. And he got all worked up, which he did great, but then started saying, "Kill Henry Hyde, kill Henry Hyde!" And Alec Baldwin got into a lot of trouble and the Secret Service called him or something. Frequent guest Rebecca Romijn-Stamos helped O'Brien hone his patented inept-flirting shtick. O'BRIEN: I always thought she was just eye-meltingly gorgeous, so it did come from a real place. But she's married to John Stamos. And I realized that making John Stamos my archrival--if you're going to mutter a name menacingly, "Stamos!" just sounds funny, you know? When she came on, I was like, Here we go. I'm going to growl at her. I'm going to hiss. I'm going to lick my fingers and wet my eyebrows. Rebecca was the first person where I really started to crack out all the bulls---. Tom Selleck had a hair-razing experience in January 2003.... O'BRIEN: We reunited Tom Selleck with his original mustache, because he'd shaved it off for a while. And I had to tell Tom that the mustache has been in a coma, and we worked it out that he's talking to his old Magnum, P.I. mustache in a little tiny hospital bed and it's saying "Tom, who's that other mustache on your face?" And Tom takes a tiny pillow off the bed and smothers the mustache and you hear the heart rate monitor go beeeeeeep.... I like the moments where if you had just turned the TV on, you could never get a brain trust to work backwards to figure out how things got to this point. V. IN THE YEAR 2006 Last year, O'Brien signed another lucrative deal, earning him an estimated $8 million a year. But his contract expires in December of 2005, raising the question, Will he be ready to replace Letterman or Leno one day in the 11:30 slot? MICHAELS: When he's called, he'll be ready. And I think he will be called. O'BRIEN: In the next couple years I may or may not get a phone call to take over for somebody. And in that moment I'll know what to do. I hope I have a phone when the call comes. Five years from now, I could be a minor character living in the pool house on The O.C., and that would make as much sense to me as anything else that's happened in the last 10 years. LUDWIN: Could Conan do 11:30? Absolutely. Our wonderfully good problem is that The Tonight Show is stronger than ever. So our goal in the next few years is to keep him happy and visible at places other than 12:30. O'BRIEN: People think you've got to move earlier and earlier to 11:30. But my theory is, like Batman, I want to move deeper and deeper into the night. Carson Daly will be confused because I will pass him going the other way. I'll get his 1:30 show and then I'll go to 2:30 and then 3:30 and by the time I'm a very old man, I'll have a mildly popular morning show in Miami. Andy and I will be just sitting there on stools with pink coffee mugs that say "Mornin' with Conan and Andy" and we'll have a houseboat that we both live on and we'll solve crimes on the side. Yeah, it's going to be good. [QUOTE:] "For a year there, it looked like I could become famous as one of the most unfunny people ever, and that was the nightmare" COPYRIGHT 2003 Time, Inc.