by Carter, Bill
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 th
at 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.
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 k
new 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.