The War for Late Night (10 page)

There had been one other demand from the Conan side, tied to their desire for some guarantee of good faith from NBC. It was all well and good to be told Conan was getting
The Tonight Show
in five years, but as even one senior NBC executive conceded, “You can’t trust network executives; they go back on their word.” The Endeavor agents were hardly going to take at face value NBC’s assurances that they would go through with the deal, no matter what the coming five years would bring. They required a bit more value.

What was needed, Ari and his team concluded, was a penalty payment so crushing, so overwhelming, that nothing would ever induce NBC to put itself in the position of having to pay it. They consequently asked for $80 million. After the usual haggling, both sides settled on $45 million. Conan’s agents plugged in various bells and whistles, accompanied by recitations about how Conan could have taken another offer to go to a different network, and how he was staying only because NBC was promising this show, and if he didn’t get it, the damage was surely worth $45 million—plus his attorney’s fees after he sued.

Simplified, the terms meant that if NBC decided to renege on Conan for any reason—other than Conan’s refusal to work or some transgression of moral turpitude—the network would be compelled to sign a check of truly imposing magnitude. It was even bigger than Dave money.

That night, with a larger audience than usual watching—it included, after all, everyone who had been involved in this protracted deal, including Conan’s lawyers, who would be checking to make sure that whatever Jay said satisfied the stipulations—Jay stepped up to his assignment.

Looking sharp in a fresh haircut, Jay sat at his desk after the first commercial and, displaying something that looked like enthusiasm, laid out the tale. Like Conan and his backers, Jay clearly dissembled on the details, making it sound as if the two NBC decisions—extending Jay, anointing Conan—had been agreed to at different points in time. He certainly implied that he had agreed with the notion that his doing the show past 2009, when he would turn fifty-nine, was untenable, because “there was really only one person who could have done this into his sixties, and that was Johnny Carson—and, I think it’s fair to say, I’m no Johnny Carson.”

Leno acknowledged that Conan was funny and “the hottest late-night guy out there.” What was unquestionably true was the rationale for the move that Jay explained, which was the same one he had expressed to Zucker and Ludwin: He didn’t want Conan to go anywhere else. Jay cited the animosity between him and Letterman that had marked the previous turnover in the job and regretted that “good friendships were permanently damaged. And I don’t want to see anybody ever have to go through that again.”

Leno ended his statement by linking the move to NBCʹs late-night doctrine of temporary stewardship. “’Cause this, you know, this show is like a dynasty,” Leno said. “You hold it, and then you hand it off to the next person. And I don’t want to see all the fighting and all the ‘Who’s better?’ and nasty things back and forth in the press. So right now, here it is—Conan, it’s yours! See you in five years, buddy!”

O
n a brisk evening in September 1981, hanging around his cluttered room in Holworthy Hall, an eighteen-year-old Harvard freshman from suburban Brookline—near enough to Cam-bridge that he could have been a commuter—had no special plans.

He had spent his first weeks wandering the impressive and imposing campus, trying on different hats, looking for a place where he might fit in. Fitting in had always been an issue for the spindly young man, who had reached six foot four but at that date weighed just 150 pounds. He was also a startlingly red figure, a mass of coppery hair and matching freckles that would have screamed Irish even if his name hadn’t been O’Brien.

Having served the previous year as editor of the school paper at Brookline High, Conan had already tried on one hat, dropping into what was called a “comp meeting” at the
Harvard Crimson
, the deadly serious, tradition-steeped daily that beckoned to those among the student elite with a calling for journalism, social commentary, and perhaps even literary pursuits. O’Brien fell somewhere within that territory, having formed a vague picture of himself working in the future as a serious writer of short fiction. Still, the
Crimson
meeting hadn’t felt right; he emerged thinking,
This isn’t me; this isn’t it.

In the days since, he had wandered around the campus pondering which other Harvard headwear he might try on, without much success. Like most everything else he had experienced in his early life, this Harvard thing was starting to feel as though it was going to be a slow build.

Then one of his suitemates, John O’Connor, poked his head in the door and asked, “You wanna go to the
Lampoon
meeting?”

Conan knew the name but not much else about the
Harvard Lampoon.
He had never even read its more popular commercial offshoot, the
National Lampoon
, in his life. In his ongoing hat survey, the
Lampoon
hadn’t figured in at all. But he had no special plans. “Well, I’ll come along with you,” he said.

At the meeting, held in the
Lampoon
“Castle”—every Harvard publication had its own pretensions—prospective contributors were given the rundown: They had to write three audition pieces. If they made the cut with those, they would have to write three more. That’s all it took: six funny pieces, and you were in.

Conan’s reaction was not immediate enthusiasm, but writing something purely out of his head—rather than having to, say, gather facts for a piece in the
Crimson—
appealed to the nascent creative side of the O’Brien brain. So that night he sat down and wrote his first piece. It was quickly approved, so he wrote another. That, too, got enthusiastic approval. The third got him hired and also put him on the fast track to becoming the only freshman on what they called the “lit board” of the magazine.

For OʹBrien, the experience was a rush. For the first time in his life, he was doing something that came easily to him and that people apparently valued. Suddenly a group of people who seemed like actual adults—twenty-two-year-olds—respected him, wanted to publish things that sprang from his imagination. And then he started hearing about former
Lampoon
writers who had written sketches on
Saturday Night Live
. That was another revelation: People got
paid
for doing this kind of thing? You could make a career out of this?

The following year O’Brien was elected “president” (anywhere else, editor) of the magazine, an unusual honor for a sophomore. That led to the even more unusual honor of holding the position for two years. (It was only the second time in the magazine’s then-century-old history that that had occurred, and the first to hold that distinction was Robert Benchley.) His funny credentials assured, Conan began, at editorial meetings, to unleash his highly energized, spontaneous, almost Dadaist comedy, hurling himself around the room, doing almost anything to make his colleagues laugh—which they did, a lot.

His pals began to tell him he should save some of this material for when he had his show. His
show
—that sounded right. An inveterate doodler, he had already created the self-caricature—outline of features, dots for freckles, big swoosh of hair—that would later become his signature. When he passed the information kiosks that dotted the Harvard campus, he would quickly sketch the little Conan head and have it saying some nonsense words like “Jub, Jub.” When people would ask him what he was doing, he would say, “It’s a promotion—for my show.”

It was all talk. When offered his first real on-campus performing gig—a chance to emcee the annual concert of the Radcliffe Pitches, an a cappella group that traditionally invited the
Lampoon
president to do the opening jokes for its show—Conan had to choke down raw panic before saying, with manufactured panache, “Yes, I’ll do it!”

He went out and bought blue index cards and started writing jokes. He acquired a white yachting cap and a big cigar. And—even paler than usual from the surging fear—he set off for his stage debut. As he sat upstairs in the big Sanders Theatre, going over his cards, praying he knew what would make these people laugh, Conan could hear the crowd below, thump-thump-thumping their feet in anticipation. He realized he had arrived at the most frightening moment of his life and found himself frozen in his chair.

A stagehand finally came to nudge him: “You gotta get out there.” So Conan O’Brien sucked in some air, stuck on his yachting cap, picked up his cigar, and galumphed those big legs out onto the stage.

He got laughs—genuine, honest laughs. The sound wafted up from the audience and enveloped him, embraced him, cocoonlike—or maybe like the ring of smoke in an opium den. O’Brien had never used drugs and never would. But this? This was the same thing; this was cocaine.

The week of graduation, the
Crimson
—now edited by a kid named Zucker—ran a series of profiles of some of the departing seniors. Conan had his own framed and hung in his boyhood room back in Brookline (where it would remain, always). It identified OʹBrien—even with his American lit and history double major, and his thesis on “literary progeria” in the works of Flannery O’Connor and William Faulkner—as the “preeminent jokester” of the class of ’85. The profile ended with a quote from Conan, answering the question “What do you want to be doing twenty years from now?”

“I want to be hosting my own show,” O’Brien replied, “and hawking my own line of designer jeans.”

 

Conan Christopher O’Brien was born in Brookline, Massachusetts, on April 18, 1963, third in a brood of six, the children of Thomas O’Brien and Ruth Reardon O’Brien—a family so deeply Irish they might as well have lived in a bog.

But they didn’t; they lived in a big, rambling, comfortable home in a lovely neighborhood, a product of conspicuous professional success. Dad was a prominent physician, a specialist in immunology, who eventually would wind up teaching at Harvard Medical School. If anything, Mom’s record of achievement was even more impressive. A scholarship student at Vassar, she graduated from Yale Law School (after turning down Harvard Law), worked on the creation of the Peace Corps for the Kennedy administration, put aside her legal career to raise her children, and returned to law and became only the second female partner at the well-regarded Boston firm of Ropes & Gray.

Their third son did not spring from the womb funny—nor academically driven, despite the parental example. Though well loved in his supremely functional and warm family, Conan felt awkward and out of place for much of his childhood. He started out with a deep distaste for school, until he saw it as a route to recognition for achievement. Then he applied himself toward excelling with a steely purpose. Too gangly to be an athlete, unwilling to turn himself into a bookish nerd, and not confident enough yet to exhibit publicly the wiseass within, he was a kid without a natural constituency through most of his precollege years.

His sense of humor was initially more defense mechanism than personal statement, and it certainly did not seem an avenue to show business for the young O’Brien. But then, what did a kid in Massachusetts, with two professional parents, know about getting into show business? “You might as well say I’m going to Mars” was how it seemed to Conan. But he loved the
idea
of show business. He loved comedy, loved to make his family and the other kids laugh. He loved comedy movies, watching them obsessively, especially the classics featuring the Marx Brothers or W. C. Fields. He took note of everything about comedy—pratfalls, verbal byplay, pure wit.

The young Conan thought the way you became an entertainer was by learning the basics—like, for example . . . tap dancing. How could you be in show business without being able to tap dance? His doting—but likely confused—parents found a protégé of Bill “Bojangles” Robinson, and Conan diligently took tap lessons for several years, the distinctly odd kid out, one white face among a group of inner-city black youths.

When that ended—as it had to, once the realization set in that vaudeville was dead—Conan channeled most of his deep reservoir of energy into shining in school. He became a grinder, especially in high school, when Harvard loomed as his goal. (The role of class clown had zero appeal; Conan always maintained that “the class clown is killed in a motel shoot-out.”) He focused on schoolwork with an intensity that few of his contemporaries could match. His mother noticed and started to believe her son was a person who would never take things lightly. Conan wanted Harvard because no one in his preposterously high-achieving family had ever gone there. But mainly he wanted Harvard because that was where all the smartest people went, and this was a smart young man who wanted to get someplace.

High school was the last time Conan was unsure where he was ultimately headed, but it helped get him on the road. He did, inevitably, give the class speech as valedictorian—and, yes, he got some laughs.

 

Being funny onstage may have been something of a drug, but from the day he left Harvard, heading for LA and a career, O’Brien recognized that one form of comedy did not fit his particular specifications—or vice versa.

He knew he wasn’t a stand-up. He had a different kind of mind, one that truly sparked only when touched to another. He was interactive—he was funny with people, and he made other people funny. Stand-up seemed a different art form, one he respected, but did not want to practice.

The notion of improv, however, intrigued him. He knew little about it, had never taken a class, or even seen it performed. But it
sounded
like him. So when he and his best
Lampoon
writing buddy, Greg Daniels, landed in LA in the summer of 1985, already hired as writers for the HBO sketch comedy series
Not Necessarily the News
, Conan spent part of his first day at the Sunset Gower Studios trying to wheedle his way into a class given by the improv troupe the Groundlings.