The War for Late Night (12 page)

Michaels had a keen feel for the psychology of talent, and he recognized that indefinable urge in talent to move on even when nothing specific was impelling them to do so. Still, he implored Conan to stay; he loved the guy’s writing. Conan didn’t offer any ultimatums, such as insisting that he be added to the cast, because he still knew that was not right for him. What was right, he still couldn’t say. But he parted with Michaels on excellent terms and pondered his next move. He had some money because he rarely spent any, so he decided to hit the road.

Not long after word got out that he had left
SNL
, Conan got a call from Al Jean. Like many young comedy types, O’Brien had been bowled over by the early years of
The Simpsons
on Fox. He was keenly aware of Jean not only as a famed
Lampoon
alum, but also as one of the top
Simpsons
writers. Jean, who had just taken over as show runner, was, in turn, well aware of Conan’s reputation on
SNL
and invited him to take one of the rare slots that had opened up on the writing staff. Not having done that kind of formal scriptwriting before, Conan temporized for a moment, but this was
The Simpsons
, after all, and he had to give it a shot.

Soon fans of the show, who were acute observers of even its smallest details (trained, as they had been, to look for the most subtle sight gags and throwaway lines), began to notice that some of the episodes they were enjoying most bore a writer’s credit with the odd name of Conan O’Brien. Conan soon had gained a reputation as a spinner of gold, never more so than in his script for “Marge vs. the Monorail,” an elaborate gag-filled quasi-takeoff on
The Music Man
, always cited by fans and critics as one of the classic episodes in the show’s long history.

Thanks to his impressive work on
The Simpsons
, Conan’s name circulated around Hollywood studios as potentially the next great creator of sitcoms. His manager (and Greg Daniels’s) at the time, Howard Klein, called to tell him that the Fox production studio Twentieth Television was beating down his door to sign Conan to an overall deal as a writer. (Studios secured hot writers by committing them to deals in which they would be paid simply to sit in a room and develop ideas for shows.) Conan suggested that he and Klein meet to discuss the offer.

In the meantime, hanging out with Lisa Kudrow, who was beginning to land parts in shows like
Mad About You
, Conan only felt the tug to perform ever stronger. He found himself getting edgy, angry even, at the prospect of restricting himself to writing. Kudrow suggested they might do some kind of Nichols and May improv act together, but then the Groundlings called with an offer to bring a bunch of alums together for a special show, people who had been associated with the troupe in some way. Conan qualified because he had finally taken some classes with them and at one point had been on track to get into the company. He enthusiastically signed on.

The show was impromptu and nerve-racking, because he had never really performed improv on a big stage before. But Conan loved it extravagantly. That night “the nickel dropped” for him. He realized he would rather make no money at all doing this than make several hundred thousand a year working as a
Simpsons
writer.

When OʹBrien had his meeting with Howard Klein, he decided to reveal to his manager what he had really been thinking about for a long time. “I really don’t think I want to sign myself up to a long-term thing as a sitcom writer,” Conan told him. “I think I need to start performing.”

It seemed to Conan that the mere mention of that word caused Klein’s face to fog over. And after some hemming and hawing, he would come back again with: “But, anyway, at Fox, we can get this fantastic deal . . .”

Conan liked Howard Klein, respected his work—but he fired him.

He started having a vague feeling that his life was changing, and he needed to be ready when the next door opened. So he asked a string of high-profile agents if they wanted to step up and explain why they might want to represent him. The agents all but lined up to pitch him their credentials. At the various meetings, Conan let them all know what he was intending: He wanted to shift to performing.

When Gavin Polone arrived for his appointment, he knew Conan would remember him from parties involving writers from
The Simpsons
, because many of them were Polone’s clients. He was now at United Talent (having been fired from ICM, the first of many contentious business separations in Polone’s career). But he had another ace to play.

Conan made his usual points about wanting to find a way to tap his urge to perform. Polone responded that he could totally understand that, because when Conan and his
SNL
friends had brought “The Happy Happy Good Show” to LA several years earlier, he had made a point of seeing the act. And he had liked it; he had especially liked Smigel and the redheaded guy. Of
course
you should be a performer, Polone told Conan. Maybe they could build a sitcom where he would write
and
star in it. Gavin was hired.

 

Still writing on
The Simpsons
, Conan spent his free time fighting off anxiety and frustration—and depression. He had always been prone to falling into an occasional slough of despond, sometimes even when things were going relatively well. Now he was picturing himself on an access road running parallel to the freeway, riding along mile after mile, looking for a ramp to get on but never seeing one. He knew he was close, so close, but he had no idea how to get onto that main highway.

Not that there weren’t distractions to alter his mood. It was 1993, and he couldn’t help but follow the tumult going on over at NBC in late night. NBC had picked Leno over Letterman as Carson’s
Tonight Show
successor—unaccountably, to an unabashed Letterman fan like Conan. Now, in the subsequent uproar, Dave was leaving for CBS and NBC seemed to have no clue how they were going to replace him.

By sheer coincidence Conan’s younger sister Jane had landed a job at the William Morris Agency. This put her in position to see confidential e-mails, and in the midst of the Letterman-Leno fracas, one that crossed her desk caught her eye: NBC was about to make a deal with Lorne Michaels that would give him control over the choice of the new host of the
Late Night
show. (NBC had to announce
something
the day Letterman was exiting; while it still had no host, it could at least tell the world that the talent maestro Michaels was on the case.) Knowing how much Lorne had respected Conan during his time on
SNL
, Jane called her brother to tip him off and assure him: This was meant to be; this is your slot.

Conan waited. He couldn’t realistically pitch himself to NBC as the replacement for David Letterman. Who the hell would take
that
seriously?

It was Lorne who did the calling, a couple of days later. Conan would compare his overture to being on the street when a meteor hits. But this wasn’t the crash at his feet; it was only the flash in the distance. The job Lorne pitched hard to Conan was as the creative brain behind the new
Late Night
show, a position that would place him somewhere between head writer and producer. Not the executive producer, responsible for the daily running of the show—Lorne had somebody else in mind for that. He wanted Conan to put his wildly inventive mind to work on the comic sensibility of the show.

Without a doubt this was an attractive offer: to put your own creative stamp on a big-time network show; to be, in essence, the Merrill Markoe of the new show, the brains behind the operation. Even so, Conan didn’t jump at the suggestion, but told Lorne about his plan to be a performer. They noodled around with a few ideas. There was the semibaked suggestion that if Conan took this job for a while, maybe he’d be in line to host the 1:35 a.m. show
Later
, which the top NBC sportscaster Bob Costas had put on the late-night map. Costas might be leaving to go back full-time to sports, Michaels intimated.

Conan hedged: Lorne needed to talk to his agent.

Polone, the new agent, didn’t have to concern himself with sounding ludicrous. He was representing a client. He flat out told Lorne to forget the producer thing: “Conan should star in the show.” He wasn’t, in fact, entirely serious. In the back of his mind he was thinking about the 1:35 show. That was Polone’s real plan—insist on the 12:35 job in order to get the 1:35 job. Like everyone else, he expected NBC to go after Garry Shandling for the Letterman job. Who in his right mind was going to suggest Conan over Shandling? Polone was now doing precisely that, but nobody could ever accuse him of being in his right mind where a client was concerned.

The issue never really came to a head, because before Polone could push any harder Conan weighed back in. As he had pondered it, in between
Simpsons
writing sessions, Lorne’s idea grew less and less appealing. Finally, kicking it around in his head one night, Conan had a violent reaction to the whole notion. He decided he just had to get out of this.

Conan called Lorne in New York to tell him thanks, but “I can’t do it.”

Michaels did not hide his disappointment. He had been counting on Conan; that was one thing about this acid-inducing situation that he had been depending on getting off his plate with minimum trouble. The conversation became a bit unpleasant, the first time Conan had ever had that kind of interaction with Lorne. But when they hung up, Conan all but fell back in his chair, overcome with relief. His only thought was:
I’m out of it. I’m done.

 

Lorne Michaels, never fazed when a live show looked as if it was about to implode, was hardly going to be ruffled by not having an easy answer to the question of who was going to succeed David Letterman. He did have a strong conviction that his choice needed to be new and fresh: No one was going to be able to stand up as a match with Letterman, so why try anyone familiar? At least a new name might start out under the radar and get a chance to grow. And young was essential, because the only way to break a new name in late night was to grab the same crowd that had made Letterman a star—college kids.

Even with Conan out of the picture, Lorne believed he had one element solved that would give him some degree of confidence. He would turn the daily control of the show over to Jeff Ross, a producer he had groomed for years for just this kind of assignment. Ross, who started as a road manager for Diana Ross (a job that included managing her famous stormy-weather concert in Central Park in 1983), segued into television when Michaels invited him to produce a series for a Canadian sketch comedy troupe, the Kids in the Hall, in 1989.

Ross wound up working on multiple projects for Michaels, including another Central Park concert, this one starring Lorne’s close friend Paul Simon. Ross had just come off a root canal of an assignment, producing a special with the comedian Dennis Miller—known for being difficult to work with—when Michaels proposed that Jeff become the executive producer of the
Late Night
show Lorne was assembling for NBC.

Ross knew he should be flattered—and he was—because this was obviously a potential career-making assignment. But he admitted to Lorne, “I don’t know if I want to do it.” He knew he couldn’t simply reject an offer like this, but the prospect of building a show that was supposed to follow a groundbreaking, industry-changing icon like David Letterman struck Ross as overwhelmingly daunting.

Lorne assumed Jeff would simply come around, and when he next approached Ross, it was in LA. “Are you going to produce this show for me?” Michaels asked.

Ross told him he was still thinking about it, but it would depend on who the host was.

Michaels looked incredulous. “What do you mean it depends on the host?”

Ross, recalling his recent experience with Miller, knew he didn’t want to live through that on a full-time basis. He repeated his concern. He needed to know who the host was going to be before he could commit.

OK, Michaels told him, it just so happened that that very night he was going over to the Improv club on Melrose to watch a showcase of comics auditioning for the
Late Night
chair. He invited Ross to come along.

The entire NBC Entertainment hierarchy was arrayed at the club, with Don Ohlmeyer and Warren Littlefield the two men in charge, thanks to their roles as the top executives at NBC Entertainment. Ross knew next to no one, so he sat quietly observing the long roster of comics. Most he had never encountered before, some he had seen perform, and a few he—and everybody else—would come to be familiar with over time. The group included veteran stand-ups, like Allan Havey, Paul Provenza, and Michael McKean (well known as a onetime member of Spinal Tap), as well as some lesser-known but accomplished comics, like Rick Reynolds, along with newcomers, like a roundish guy in thick-framed black glasses named Drew Carey and a witty, compactly built guy with long hair named Jon Stewart.

After the long show ended, the NBC group crossed the street to a restaurant for a postmortem. Nobody’s name seemed to be rising to the surface in the discussion, which hardly surprised Ross. How could it? They were all sitting there thinking the same thing:
Not bad, but he’s sure not Letterman
. Ross judiciously kept silent, but as the group was leaving, Lorne approached him. “There’s a meeting tomorrow in Littlefield’s office; I want you to come.”

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.