The War for Late Night (11 page)

Crushed to learn that all the classes were filled, Conan said he had to do something, so they recommended a woman named Cynthia Seghetti, who taught at the Coronet Theatre. When Conan turned up there, he realized it was extremely informal, the kind of class where you stuck ten bucks in a jar when you left. The students, such as they were, seemed engaged in various exercises. One was “space work”—doing things like pretending to lift an imaginary heavy desk. Conan went at this assignment with his customary 100 percent conviction—so much so that an attractive tall blond girl came up and complimented him on his commitment to the exercise. Her name was Lisa Kudrow, and a long, sometimes romantic, always warm relationship was born.

The group performed improv in places like the basement of the Scientology Center, where it was almost impossible to get audiences because people were afraid of being shanghaied on their way in. There was no money in it, but money wasn’t the point; O’Brien was already making a fine salary for an LA newcomer, thanks to his HBO job. But in off hours he was also accepting oddball assignments like industrial videos, driving two hours out into the San Fernando Valley in his 1977 Isuzu Opel, applying his own makeup during the drive. Often he played the know-it-all salesman whose technique drove the customers away. He would make up patter on the spot—something else he discovered he had a talent for. The level of gratification in this sort of acting was as slight as the pay, but it was an opportunity to perform.

Mainly, he was writing. The
Not Necessarily the News
job soon led to another gig: O’Brien and Daniels, already making an impression, were hired by a new late-night show concocted for the Fox network and touted as being the first real alternative to the staid talk-show format.
The Wilton North Report
—a bizarre amalgam of fake news and silly gags—lasted less than two months. O’Brien figured it was good experience doing “service on a ship that sank.” Plus he occasionally got to warm up the (sparse) crowd.

But Conan knew in his gut the show he really wanted to write for—the show that had so captured him with its comic sensibility that he cringed with regret when it was impossible for him to catch it every night when he was in college. Everything about what David Letterman was doing on his NBC
Late Night
show spoke to the creative core of Conan O’Brien, and he was spurred by the possibility that he could someday write for Dave and find ways to satisfy his jones to perform at the same time. His inspiration in that regard was Chris Elliott, the young Letterman writer who had become a regular performer on the show, creating off-the-wall characters, most memorably “The Guy Under the Seats,” in which he played a nutjob who lived beneath the seats of Letterman’s studio.

Conan finally put together a packet—a collection of comedy pieces based on what the show was then doing, including monologue jokes, material written for established sketches, and some the writer would invent—sent in his submission, and waited for the good news.

The wait was considerable, because writing openings on Letterman’s show were rare and, with a sizzling-hot show on their hands, the staff was flooded with submissions. But Conan’s packet eventually made its way to the top of the pile, and when the first opening in a long stretch came up, he learned he was in contention for the spot with just two other guys. One was a kid named Rob Burnett, who had been on the Letterman staff for a while as an intern, receptionist, and anything else he was asked to do; the other was an advertising copywriter from Oklahoma named Boyd Hale.

The show went with Hale. Steve OʹDonnell, the already legendary head writer for Dave—who had succeeded the equally legendary Merrill Markoe, Dave’s first head writer and also once his longtime girlfriend—called Conan with the bad news. O’Donnell, himself a
Lampoon
alum, told Conan, “Dave doesn’t want to go with another Harvard guy.”

The news devastated O’Brien—he had been
that
close to working for his idol. The disappointment lingered for some time, although it would be mitigated somewhat years later when Dave, after being reminded during an interview that Conan had almost been a writer for him, replied wistfully, “Well, our loss.”

Within months of that setback, however, he and Greg Daniels made it past another of television’s toughest cuts and were hired as staff writers for
Saturday Night Live
.

The show, by then just into its second decade and with Lorne Michaels back in charge after his self-imposed interregnum, had been the incubator for a generation of comedy talent, in both performers and writers. Landing there in 1987, with a new cast (Phil Hartman, Dana Carvey, Jon Lovitz) about to explode, Conan thrived, though the fit always felt imperfect to him. Something about what Letterman did, the everydayness of it, simply appealed more to him. At the same time, breaking through as a performer on
SNL
given the existing lineup posed a forbidding challenge. Conan wasn’t a mimic on the level of Carvey; he couldn’t create and lose himself in characters the way the phenomenal Hartman did. Conan knew that whatever part he might play in a sketch, his sheer Conan-ness would burn through.

What his
SNL
stint did accomplish was to expose his burgeoning writing skills to a critical group of contacts. Lorne Michaels, chiefly, made note of the new kid’s remarkable facility to write any kind of comedy and marked him as someone to keep his eye on. Conan was also slaying longtime
SNL
presences like Jim Downey and Al Franken with his spontaneous bursts of silliness. And he found a kindred spirit in Robert Smigel, a young writer with swagger who had been among the few to survive a staff purge by Michaels at the end of the 1986 season.

When a writers’ strike hit the TV business early in 1988, shutting down production on
SNL
, Smigel and another staff member, Bob Odenkirk, decided to try creating a stage show of sketches too outrageous (they thought) to ever make it onto television. They had witnessed some of O’Brien’s wilder moments in the writers’ room and perceived someone like themselves: a performer caged inside a writer and not so quietly thrashing in the effort to get out.

Smigel and Odenkirk, who had made their first comedy bones at the Players Workshop in Chicago, asked Conan to join them in a show they were putting together that they would mount in Chicago that summer. It sounded to him like a fantastic adventure, and Conan jumped on board.

The income from this exercise figured to be so minuscule that Conan asked his new partners if they knew of some way he could save on housing expenses. Odenkirk, as it happened, had a friend with an apartment that might have an empty room, and a call secured the space. Jeff Garlin, then twenty-six and himself just trying to break in as a stand-up, had rented a place in his native Chicago within steps of the home of his favorite team, the Cubs. All he had to offer was a tiny room with no window and barely big enough to squeeze in the futon Conan was going to use as a bed. O’Brien took one look and concluded, “Not even by prison camp standards is that a room.” But it was cheap, and he didn’t expect to spend a lot of time there anyway.

Most of his time was going to be consumed first with putting together and then with staging the review, which they had decided to call “The Happy Happy Good Show.” They rented out the Victory Gardens Theater on North Lincoln Avenue and got ready to rock and roll.

Conan had written a few sketches with Daniels. In one he played a character called “Kennedy Baby” and simply rolled on the ground in a diaper, saying “a dep, a dep, dep,” and other gibberish in a Kennedy accent. For another character, “Spoon Eye,” he came out holding a spoon over his right eye and in supercilious fashion would ask for questions from the audience. Whatever anyone asked of Spoon Eye, from politics to the weather, the answer would always contain the word “spoon.”

The biggest hit of the “Happy Happy Good Show”—and there weren’t many, because even the performers thought the show was only erratically funny—was a sketch Smigel had created called “Chicago Superfans.” Later a legendary
SNL
sketch, it featured a mustachioed character named Bill Swerski and his deeply Ch-caeh-go-accented mates celebrating coach Mike Ditka and “Da Bearss” with copious quaffs of lager and mounds of Polish sausage.

That summer of 1988 in Chicago was torrid at record-setting levels. Conan’s little windowless cell had no air-conditioning. He would return from the theater and enter the hot box like Colonel Nicholson getting into the corrugated torture oven next to the River Kwai. He would collapse onto his now permanently sweat-soaked futon, but not before he and Garlin spent some quality time together deconstructing their lives and careers, with Conan frequently setting off on one of his unfettered comedy rolls. Garlin would sometimes wake O’Brien in the middle of the night because he wanted to hear again something that Conan had said that destroyed him earlier in the evening.

But nothing killed Garlin quite like one regular bit he and Conan cooked up that sweltering summer. Joan Rivers had just flamed out in her effort to start up a late-night show for Fox, and the talk in the comedy business was about possible replacement shows and all the different names people were kicking around as candidates. Without any kind of forethought, sitting around the apartment, O’Brien and Garlin fell into a byplay that quickly took the shape of a new talk-show entry, one they called, for no apparent reason, “Wild Blue Yonder.”

Conan played the host—but not as himself. Instead he pulled up his deadly impression of the onetime
Star Trek
actor George Takei. In this conceit, Takei had somehow landed the new Fox talk show. And every night he had the same guest: Jeff Garlin. They created an ersatz set with host base behind a coffee table and guest on the couch. Almost every night they would fall into doing the show. Conan as George Takei would ask Garlin about his act and touring: How was that going? Garlin would go along for a time, but eventually he would come around to asking Takei about those residuals from
Star Trek
: And how were they coming along? After first trying to be dismissive, or to change the subject, Conan’s Takei would start to become agitated and then bitter about how he’d been cheated on his residuals. And the interchange would get out of hand, with Takei ever more furious.

The bit slayed Garlin. He marveled at Conan’s ability to wind the Takei character up ever tighter. All summer they went back to “Wild Blue Yonder”—always only for themselves. It did not make Garlin picture Conan as a future talk show host—maybe because he was always George Takei. But he was blown away by Conan’s comedy mind.

When the summer ended, Conan dragged the disgusting futon out of his steam room and threw it away. On his last night in Chicago, though, he had to have George Takei sit down one last time with Jeff Garlin.

Again, Takei tried to explore the homey details of Garlin’s emerging show-biz career, but as soon as Jeff went to the indignity of those missing residuals, it proved too much for George Takei. He howled to the moon and committed seppuku on the spot.

“And that was the end of ‘Wild Blue Yonder,ʹʺ Garlin said.

 

The cast took “The Happy Happy Good Show” for a two-week run in Los Angeles, hoping it might burnish their comedy reputations a little. It didn’t, but it was by chance seen by a young agent for ICM named Gavin Polone. He enjoyed it and was particularly impressed by the tall redheaded guy.

In mid-August, after five months and seven days, the writers’ strike ended, and everyone from the stage show returned to New York and the new season of
Saturday Night Live
. Conan settled back into his writing assignments, relishing the times that he got little on-camera shots on the show, like “handsome guy in the background.”

Conan had idiosyncrasies unusual even for
SNL
. Though he loved to be in the writers’ room kicking around ideas, when he got down to the actual word-on-page process, he would sometimes like to wander off with Greg Daniels—the way they used to at Harvard when they had to study for an exam. At
SNL
they took to drifting through the floors and halls of 30 Rock, looking for the best place to get inspired and write. At some point this led them to the sixth floor and the entrance to Studio 6A.

To their amazement, there was no guard there, nothing to stop them from drifting in and checking out the place where it all took place every evening. The Letterman studio, which always shocked fans when they turned up in the audience because it was so much smaller than it looked on TV, was as quiet as a church late at night when OʹBrien and Daniels moseyed in. Dave’s desk had a plastic covering over it, but it didn’t stop Conan from stepping up and planting himself in the chair, Dave’s chair, facing out into the empty seats of his audience, while Daniels, the undemonstrative partner in the pair, would find a seat down in the first row. There they would sit, Conan behind the desk, conducting a writing session like Dave conducted an interview.

It wasn’t as if he were a kid in a “look at me” moment, sitting behind the wheel of Dad’s car in the garage. Nor was it a sign of any innate audacity; if someone had walked in, he would undoubtedly have been embarrassed and fled the scene. But sitting there, in the dim light, at
that
desk, looking out into
that
studio, the sensation, the aspect, felt right to Conan. He found himself thinking,
What this guy is doing, this is the kind of thing I could do. It wouldn’t be the same way he does it. I’m not a precision instrument like David Letterman. But when I am having fun and I’m in the moment, there’s nothing else like it. . . . If only I could figure out a way . . .

 

In 1991, having established himself as one of the hottest writers on the show, Conan told Lorne Michaels he was quitting
Saturday Night Live
. While the decision didn’t make sense—he had no other job—all Conan could think of was salmon swimming upstream. They don’t know why they’re doing it; they just have to do it. The vaguest of feelings was telling him he had to leave
SNL
, had to get out of New York for a time and do—whatever.