The War for Late Night

by Carter, Bill

  The request struck Ross as slightly surreal. He hadn’t accepted the job, they had no host, and no one had any idea where they were going to find one. But now he was going to sit in on a meeting with the NBC bosses at the network’s Burbank headquarters.

  When he showed up the next morning he was accepted without question as “Lorne’s guy.” Again Ross said nothing as the execs began batting around names; again nobody was compelling. Lorne wasn’t crazy about the idea of a pure stand-up as host, in any case—they always seemed to want to score, and that approach didn’t work when talking to guests. For his part, Ross kind of liked Stewart; he had previously worked with him at a New York Comedy Festival and was impressed by his quick comic mind. But nobody solicited his opinion.

  Then, out of nowhere, somebody asked about Conan OʹBrien: Was he going to run the writing for the show? Michaels explained that Conan had decided he didn’t want to do it. He had his mind set on turning himself into a performer.

  That seemed to stop the conversation dead. After a pause, Lorne had another thought: “Hey, maybe Conan can host it.”

  Few in the room had a clue who this Conan guy was. But Warren Littlefield did; he knew him from his SNL background and from his reputation as the hot writer from The Simpsons. It didn’t seem to strike Warren as all that crazy an idea. “Well, should we test him, maybe?” Littlefield asked.

  For reasons Ross could not fathom, Lorne turned to him and said, “Well, can we test him?”

  The first thought that popped into Ross’s head was, What the fuck do I know? But what he replied was: “Yeah. Sure, we can test him.”

  Conan got the call in his office at The Simpsons. It was Lorne, in that hypercalm voice of his: “We haven’t found anyone yet. Would you consider doing a tryout?”

  Fear? Yes, for sure. Disbelief? Naturally, but there was no time for either. “Yes, of course,” Conan said. “What’s the harm in trying?”

  What Conan had also been feeling was something eerie; he had been feeling it for months, since before he had parted with Howard Klein. Something was coming for him. Maybe it was an oncoming train—or maybe a ticket on that train. But it sure felt like something was coming.

  When he got home that evening to the apartment he was renting on Wetherly Drive at the edge of Beverly Hills, Conan tried to make sense of what might be happening. Before he could get too far, his phone rang. It was Michaels again.

  “Whatever this audition is going to be, you need to meet with Jeff Ross,” Michaels told him. “Jeff’s going to produce it. You guys should arrange to get together and talk it out.” Conan agreed, took Ross’s number, and called as soon as they hung up.

  He introduced himself to Ross, who had obviously been waiting for the contact. “Where are you?” Conan asked. Ross told him he was staying at the Four Seasons—a very short walk from his apartment on Wetherly. “I’ll come over and meet you in the lobby,” Conan said.

  When he arrived, he called Ross, who said he’d be right down. As he waited Conan looked around and noticed that directly past the concierge’s post in the lobby was a small officelike room with a faux fireplace. It also had a desk. Without hesitating, he slid into the chair behind it.

  When Ross entered the lobby a few seconds later, he quickly spotted the guy he was looking for: really tall, really red. Ross walked over and held out his hand. “I’m Jeff.”

  Conan extended his arms wide over the desk, slapped both hands down on top of it, and said, “Whaddya think?”

  “Well,” said Ross, looking at this guy behind a desk in a hotel lobby pretending to be on television and wondering just how crazy this was going to get. “I, uh . . . I—I . . . guess?”

  Conan had only a couple of weeks to get ready. He worked on writing a little monologue, but had to cover a few more bases. Not only did he own no suits, but he didn’t even own a sports coat. He contacted Lisa Kudrow, his one female confidante at that point in his life, and they went jacket shopping. They picked out a pale linen sports coat—a little casual, yes, but that was what they were going for. What they weren’t going for would only become apparent on the air—a pale coat on a pale face was not a good look.

  Polone weighed in with some help. The actress Mimi Rogers was a friend; she agreed to act as a first guest. Larry Charles, one of the top Seinfeld writers, was a Polone client; he helped get Jason Alexander as a second guest. NBC carved out some time in Jay’s studio at The Tonight Show. Ross took care of the details, and though the process was rushed, it would do as a reasonable facsimile of a late-night show.

  On the evening of April 13, 1993, Conan arrived at the Tonight studio, possibly among the few present who could compare what was about to take place to a Pirandello play—though almost all of them surely appreciated that it was all a little absurd. Ross fell easily into the flow of production, but he more than anyone else recognized just how bizarre the situation was. This kid nobody knew was going to sit on the set of The Tonight Show and try to justify NBC’s picking him to replace David Letterman. It was totally nuts.

  Conan was not suffused with fear—this was nothing like Harvard and the Radcliffe Pitches. It was too crazy to get wound up about. Sure, it loomed like the ramp onto that dreamscape freeway, but the circumstances of how it had come together were so bizarre. Why get overwrought about something that wasn’t actually real?

  Robert Smigel had checked in to help with a few of the jokes. The Tonight Show researchers had dug up information Conan could use in talking to Rogers and Alexander. All he had to do was walk out and pretend he knew what he was doing.

  Conan waited for that night’s taping of The Tonight Show to end. As he hung out in the hallway backstage, Jay came by after closing the show. Spotting the tall guy in the ill-fitting coat—he had obviously been clued in to what NBC was up to—he stopped briefly and said, “Oh, Conan,” in his earnestly pleasant way. “Oh, hey!” Jay’s greeting seemed to echo in the air like a distant train whistle as he went by.

  After the seats were cleared the audition audience was brought in, many of them NBC types, others guests of either Conan or Polone. A few minutes before he was to go on, someone told Conan he had a call in the control room. It was Lorne, back in New York. He would be watching on the satellite feed.

  “So listen,” Lorne was saying in his apparently half-distracted way, lowering the flame on Conan’s kettle, making sure he didn’t get to a boil. “You know, nothing is probably going to come of this thing tonight. . . .”

  Conan interrupted him. “Lorne, listen. It’s going to be great. I’m sure of it.” The line had been unplanned, but it was the truth. He wasn’t sure exactly why he had said it, but he was sure of one thing, something that probably nobody out there in that audience would have believed: He was not scared shitless.

  And then he was onstage, standing on his mark, acting like a real entertainer. He looked more sheepish than anything else, a point he underscored with his jokes, which mainly had to do with trying to explain precisely how he came to be standing there that night. “This is the result of a drunken wager between Lorne Michaels and Don Ohlmeyer,” he said. With his arms swinging loosely and his indifferent posture, he didn’t look like a guy accustomed to standing up and telling jokes—but he didn’t look bad, either. Something close to charm managed to filter through the awkwardness.

  His quasi-monologue finished, O’Brien made the crossover to sit in Jay’s chair behind Jay’s desk. He read the prepared introduction, and Mimi Rogers stepped out, looking a bit as though she was worried that she had stumbled into a Candid Camera bit. But she quickly turned giggly and seemed to warm up to the kid behind the desk.

  At one point, after Conan asked about her modeling career, Rogers started to explain what hard work modeling was—much harder than people thought. Conan responded with his best unscripted line: “No. People always say being a model is hard. Turning a big crank, that’s hard”—and he mimicked great effort with a crank (not unlike trying to lift an invisible desk). He scored—with Rogers, who
laughed effusively, and also with the little audience in the studio.

  During an ersatz commercial break Jeff Ross approached from where he had been standing off camera and leaned in to straighten Conan’s tie a bit. “How’m I doing?” Conan started to ask. But before he could finish the question Ross held up a piece of paper. On it was written, “You’re killing.” Then he walked away.

  Conan chuffed up, having concluded, At least I’ve won him over.

  As he left the studio that night, Conan felt he had done well, surely better than anyone expected. As he replayed the audition, he started to feel real joy—euphoria, even. He let himself dream: Shit, I think something’s going to happen now.

  Over the next week, however, the inside word was that NBC was hard after Shandling. For his part, Lorne was still positive. “Bob Wright really loved your tape,” he told Conan. Conan asked, “Who’s Bob Wright?” Then one morning a Simpsons colleague walked into his office and casually asked, “Hey, have you seen Variety today?”

  Conan rushed out to the newsstand on Fairfax Avenue. The headline was on the front page: “Talks of Conan for Late Night at NBC.ʺ It was the first time he had seen his name in print since the Crimson. He imagined people all over Hollywood asking, “Conan who?” and “What’s a Conan? Sounds like a joke name.”

  That same day the call came in: Get to Ohlmeyer’s office for a meeting. So he sped over to Burbank, where he faced another gathering of NBC princes. Ohlmeyer, who seemed intrigued by O’Brien, led the meeting, seconded by Littlefield, who seemed openly skeptical. “The Wrights really loved your tape,” Ohlmeyer said. (Conan wondered: There’s more than one?)

  “Here’s the thing,” Littlefield chimed in. “The tape’s OK, but what kind of show would you do?”

  Conan had not really prepared a formal treatise on this subject, but he had, after all, been thinking through every aspect of having his own show since about the time he gave up tap.

  He leaned forward in his chair and, as though possessed by a demon, let fly:

  “Letterman’s done irony. He did the anti-talk show. This show has to have a different quality. I think the time is right for silliness. Dave’s got that dignity and that personal space. My thing is, I don’t really do that. I do silliness. We’re going to do things like have plants in the audience—not unprofessional performers like Dave uses, but real performers who will actually commit. If someone stands up in the audience and pretends to be a gold miner, they’ll be an actor playing a gold miner. The show will have a little bit of a Pee-wee’s Playhouse feel to it. We’ll have puppets; I think we’ll try to use animation. We’re gonna have fake guests. We’ll bump a guest every night, an actor who will pretend to be really passive-aggressive and pissed about being bumped over and over.”

  Conan sensed that Ohlmeyer had sparked to some of the ideas—especially the fake guests. Littlefield remained impassive.

  OʹBrien left the meeting feeling even more confident than he had after the test show—it had the flavor of a second audition, or maybe an oral exam in college. That evening he spoke with his sister Jane. “I think I may have just talked myself into that job.”

  The NBC executives did like what he had to say. There was a freshness about him that was appealing. But come the fall, they were facing the biggest challenge the network’s late-night empire had ever taken on: David Letterman on CBS. If Tonight took a hit, certainly Late Night would as well. More than $70 million in ad revenue was tied up with that show. The fallback position was to sign Conan as backup to Costas for the Later show—the plan that Polone seemed to be promoting in the first place.

  At that point NBC made a full-out run at Shandling, with a financial offer that had grown to nearly $5 million a year. Shandling pondered for about a week. Finally, on April 26, with Ohlmeyer fed up and opposed to spending that much anyway, Shandling let NBC know his decision: no.

  Jeff Ross, back in New York, had no idea what was going on. The tryout had convinced him that he and Conan could work together well, so he had committed to Lorne. But things had gone quiet. On the twenty-sixth, he came back from lunch and saw a stack of messages waiting. He knew at once: “Oh my god, he got it!”

  Later the same day in LA, Conan was at a table read of another Simpsons episode. The phone rang as the session ended, and the person who answered said, “Conan, it’s for you.” He picked it up and heard Gavin Polone say, “You got twelve thirty.” This time Conan was not euphoric, the cold calculation of what this meant starting to sink in. It was the be-careful-what-you-wish-for moment. Polone said Ohlmeyer would be calling in five minutes.

  Conan was far enough away from his bungalow office that he needed to sprint across the lot to get there. He was slightly out of breath when he grabbed the ringing phone and heard the news officially from the top NBC West Coast executive.

  The life change began instantaneously. That night, Ohlmeyer told him, Conan would do a walk-on with Jay to be introduced to the nation. A few days later they would fly him east, and he would meet the press in New York.

  Back at the Tonight studio that night, Jay brought him on with appropriate fanfare and not a little curiosity. Conan, in a new (dark) blazer over jeans, looked mildly stunned by the latest developments in his life, though he made the point—several times—that he was thrilled.

  Over at CBS Letterman addressed the news on his show. He called Conan “the new guy” and said, “I don’t know him. I heard he’s a nice boy. The only thing I heard about him is he killed a guy once.” He made the subject of that night’s Top Ten List tips he could offer the new host. Based on his own contentious relations with NBC management (and its parent company) as well as several famous incidents Dave had had with a stalker, these included: “GE executives are pinheads,” “NBC executives are bone-heads,” and “Don’t panic if you find a strange woman in your house.”

  Desperate for any information on the new guy, reporters contacted anyone who had worked with O’Brien. Most of his former colleagues had the same reaction: really funny guy, does wild, spontaneous things for no apparent reason. Matt Groening, the cartoonist who created The Simpsons , said Conan made perfect sense as the choice for a talk-show job: “He can keep a room of seething, self-hating, resentful comedy writers laughing for minutes on end. He does a lot of shtick and runs around the room. It first makes you laugh, then gets annoying, then exasperating, and then comes full circle and makes you fall out of your chair.”

  NBC didn’t even have a photograph of him that could be sent out with its press release, as Conan had never bothered to take a head shot—the principal calling card for any would-be performer. Every story wound up being illustrated with the same picture, lifted off the air: Conan with a goofy smile on his face towering over Leno on the Tonight stage. Conan found himself suspecting he was coming off like the Chauncey Gardiner character Peter Sellers played in the movie Being There. He pictured the CIA going though his suits in his LA apartment, ordering people to “pull the file on Conan O’Brien! There is no file? Pull the tape! There is no tape?”

  NBC scheduled his press debut at the Rainbow Room in 30 Rock for a week later, on May 3. That day Conan proved he had some mettle. When he entered the building, he stepped into an elevator and was immediately confronted by a reporter from the New York Post, who taunted, “I counted how many laughs Letterman got in his press conference leaving the show and I’m gonna count how many you get!” Far from throwing Conan, the encounter relaxed him. It was when things were calm that he leaned toward depression or panic. When his back was against the wall, he seemed to do things he didn’t know he could do.

  The press was charmed. Far from shrinking in the spotlight, Conan seemed to grow in it. He acknowledged being a “complete unknown.” He sparred with John Melendez, “Stuttering John” from Howard Stern’s radio show, exposing the silly disguise he was wearing. Conan seemed boyish, clever, fast with his wit, and fully appreciative of the absurdity of the position he was in. To buck him up, Lorne told him that day of an observation on
e of his fellow SNL writers, Bonnie Turner, had offered: “All I know is that guy will charm the shit out of any crowd.”

  For Conan O’Brien nothing would ever quite match the thrill of that first time—his introduction to the American television audience on September 13, 1993. The first look anyone got of him was a pretaped cold opening—a segment run before the credits—in which young Conan strolled cheerfully through Manhattan, greeted by vendors, cabbies, and passers-by, all of whom had the same helpful message: “Lot of pressure—you better not screw this up.” When he arrived at the NBC building, he ran into the news anchor Tom Brokaw, who was sterner, and more specific: “You better be as good as Letterman—or else.”

  Finally alone in his dressing room, showing no ill effects and whistling merrily, Conan pulled out a chair, stepped up on it, and in the same cheerful way swung a noose around his neck. In perhaps an inadvertent callback to the night of the Radcliffe Pitches, a stagehand knocked on the door to say it was time to go on. “Right now?” Conan asked meekly and then climbed down with a shrug, ready to step out onstage.

  That introduction stamped him as an entertainer with obvious charm and pluck, and it was those qualities that dominated the early comments about the show. In The New York Times John O’Connor assessed the opening night as better than anyone could have expected, observing, “There’s a fine lunacy here that bears watching.” Others interpreted that lunacy as an indication that Conan was jumpy, tense, and ungainly. But in truth, he had not been overly anxious that first night. What looked like nerves was actually excitement. A charge had been lit under him; he was exploding with the thrill of knowing: Yes! This is it!