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Conan O’Brien’s Three-Year Overnight Success

What’s he got that you don’t? A Harvard degree, nearly $2 million a year, supermodel neighbors, an annoying laugh and the hottest comedy show on TV

Host, Conan O'Brien, Andy RichterHost, Conan O'Brien, Andy Richter

Conan O'Brien during the 'Art Depreciation' skit on August 28th, 1996.

Norman Ng/NBCU Photo Bank/Getty

You can call it fate or you can call it breaking and entering. The differences are marginal. The time was the late ’80s, a simpler period somewhere before the fall of the Berlin Wall but after Billy Squier had taught us “The Stroke,” a time when the phrase “late-night wars” had yet to be invented. Back then, while David Letterman was quietly building an empire in the hours past midnight, a young Harvard grad named Conan O’Brien was making his way as a writer for the recently resuscitated Saturday Night Live. Every now and then, to get a break from all-night writing binges, O’Brien would sneak downstairs, pick the lock to Studio 6A, pull the tarp off the host’s chair and attempt to write comedy while sitting at Letterman’s desk. “It wasn’t like, ‘Someday I will sit here,’ ” says O’Brien. “It was more like, ‘This is where he sits? Cool.’ ” He laughs – you know the sound: high-pitched, slightly braying – and continues. “Really, the point of the story is that NBC has terrible security, and I’m sure now every night there will be a different weird person sitting at my desk.”

It is sunday afternoon, the day before the staff is to return from vacation, and the 33-year-old O’Brien, all 6 feet 4 inches, obsessed workaholic of him, has come into that very studio to assess the new set that has been built for his show. His show. Gone are the tacky, Ikea-style desk and cheap paneling. In their places stand a plush new couch and a kind of festive blue-and-purple wall ornamentation that suggest O’Brien is enough of a network commodity to warrant a set that looks a bit like a brothel.

O’Brien walks around the couch, idly strumming an electric guitar, telling stories and making suggestions.

“The carpet has to go,” he says. He pauses, as if this has been too demanding. “Don’t you think?” And then, perhaps remembering he’s the boss, he answers his own question. “We need to make sure it’s gone by Tuesday.”

He strums some more and wanders into his dressing room, where an all-too-large picture of Robert Stack stands guard over a punching bag, a Nautilus machine and a pile of rockabilly CDs. He sets down the guitar. The studio and dressing room are still the temperature of an ice-cream truck, but that is the only noticeable nod to the Letterman legacy. These days, as O’Brien nears his third anniversary and the show celebrates its first Emmy nomination for comedy writing, O’Brien is more in competition with himself than the ghosts of talk shows past.

This is not a story of Conan O’Brien, happy accident. It is the tale of Conan O’Brien, paradox: professionally goofy but with a work ethic that he calls “almost humorless.” He was the editor of the Harvard Lampoon for two consecutive years. When he left SNL to become a writer for The Simpsons, producer Lorne Michaels – who also hired him for the Late Night job – kept O’Briens office empty, his name still on it, for a full year, just in case he might return. O’Brien is both a pathologically serious soul and a pointedly funny writer and performer. He has always been focused – working 12- to 16-hour days, decompressing just enough to enjoy a Saturday evening off, then setting his mind to worrying again by Sunday night – but now the show is reaping the benefits of his neuroses.

“Until now, all my life, professionally, it felt half-right, but it wasn’t exactly what I wanted,” says O’Brien. “So when this show eventually stops and is replaced by an hour of country & western music, it’ll be difficult for me to do something different. I don’t know what I could do to make me this happy.”

He falls silent for a moment.

“Fortunately I didn’t think about it too much when things were real rocky,” he adds.

The first time we ever saw Conan O’Brien on the air, he was strolling cheerily to work for his debut while every passer-by taunted him with, “You better be as good as Letterman.” Children, old ladies, even horses: “You better be as good as Letterman.” When he finally arrived at the studio, O’Brien sauntered happily to his dressing room, took out a noose and started to hang himself, only to have a stage manager show up.

“You’re on, Mr. O’Brien,” the stage manager said.

O’Brien looked at the man and asked, “Now, or do I have a minute?”

The man was emphatic: “Right now.” O’Brien shrugged, removed the noose and took to the air.

It didn’t take long, however, before NBC executives were wondering if they should have given him a little extra time to himself. That laugh. The nervous tics. That sidekick. Those ratings. The only positive attribute ever noted in the show’s early daze was a daring array of musical acts, but that was not enough to quiet the rumblings. Rumors of cancellation popped up more often than high-fives at a frat party. When NBC hired Greg Kinnear to host Later, the show that follows Late Night, most people assumed that O’Brien was, at best, a seat-warmer for the snarky pretty boy. “I’m afraid to say we probably don’t know how close we were to getting canceled,” says Late Night producer Jeff Ross. “Part of me has a morbid curiosity. I think we got a lot closer than we think.”

But all of that was nothing compared with the barrage of personal insults that awaited O’Brien and his sidekick, Andy Richter. It wasn’t so much that critics didn’t like the show, they just plain didn’t like O’Brien and Richter.

I have heard every euphemism for fat,” says Richter, a veteran of the Chicago improv scene. “It’s incredible. They don’t say, “The black actor Denzel Washington,’ or, ‘The medium-build Kevin Costner,’ or, The small, Jewish Dr. Ruth.’ But they say fat, chubby, portly, cherubic. All of which is fairly emasculating.”

Still, the noose stayed in the briefcase. O’Brien’s friends and family stress that, yes, it was a dark period, but, no, his confidence never waned. “The lows were probably as low or lower than people might think,” says his sister Jane, a writer on Cybil. But what became clear is that although it’s gut wrenching to read attacks in the press, at least his name is in the paper. Which means he must still be on the air.

I’m a realist,” says O’Brien. “I live in America in the 1990s, and I entered the ring of pop culture. I’m not going to lie to you. The criticism hurts. But what really saves you is that you have a show to do every day. You don’t have much time to sit around and say, ‘Maybe my laugh is awful, and maybe I do fiddle around too much; maybe I am awkward.'”

And then a funny thing happened on the way to extinction. Several, actually. Like Devil-Bear, a sketch in which O’Brien receives advice from a devil on one shoulder and a bear on the other – except that the bear is only able to give tips like, “When scratching yourself against a tree, do not use a pine tree or you will get all gooky.” And remote segments from events like 1994’s Woodstock concert and the MTV Video Music Awards, in which the overweight Richter has consistently proved himself to be one of the show’s most invaluable assets.

But the biggest difference is O’Brien himself. Where he once appeared more shocked than the rest of us that he was actually on television, now he is comfortable. The program was always intended to be a bizarre sketch-comedy show that just happened to include interviews – a type of alternative universe where men dressed up as flowers dance on the Brooklyn Bridge – and a large number of the show’s original staple comedy pieces (In the Year 2000) continue to be used.” All the plates were in the baby’s skull,” says O’Brien. “They just hadn’t fused yet.” Viewership is up 18 percent from the first year, and Late Night‘s audience has a higher percentage of 18- to 49-year-olds than that of Leno or Letterman; Washington Post TV critic Tom Shales, who once called for O’Brien’s big-haired head on a stick, is now the show’s staunchest supporter; and for the first time, NBC has ponied up the cash for an anniversary show.

Then again, Late Night draws its guests from the celebrity JV squad and is still capable of missing wildly. On any given night, viewers might wonder what cable-access staff has taken the NBC studios hostage (the recent Nerdy Guy on Pommel Horse at the Beach springs to mind). But the laugh-to-cringe ratio is high enough to warrant a little forgiveness. Not to mention that O’Brien has turned into an excellent interviewer; He actually listens.

“I think the home audience needed time to trust Conan,” says original head writer Robert Smigel, a friend of O’Brien’s since they were writing partners at SNL. “We had sort of a cocky attitude. We really set out to do weird stuff. We just wanted to blow people away with how different the show was. But it is really about the host and about trusting the guy.”

Talk around NBC initially centered around placing that trust in Garry Shandling, but that quickly fell through. Ironically, O’Brien was asked to be the show’s producer and briefly helped search for a host before executive producer Lorne Michaels finally gave in to O’Briens suggestion – “How about this Conan guy?” – and called to inquire if he’d like to audition himself. In the end, O’Brien was the only person screen-tested.

“When I got this assignment, I thought I would not be predisposed to like the guy who replaced David Letterman,” says O’Brien. “So I probably wouldn’t have given me high marks in the beginning.”

He laughs – you know the sound – and then continues: “But now I’d really be into me.”

When he is on, which is often, Conan O’Brien possesses the kind of personality for which Ritalin was invented, often penning sketches for his writing staff in which he bounds across the room, acting out every role. “Even as a writer, I was a performer,” says O’Brien. “I tried to be the kind of guy who could shut the door and come out five hours later with something funny. But I was never any good at that. At The Simpsons and Saturday Night Live, I was someone who would go to people and act it out for them.”

True to his word, O’Brien will launch into long, spontaneous monologues. He claims to not believe in studying comedy theory. Ask him what makes him laugh, and O’Brien will tell you, “The funniest thing in the world is when someone is acting foolish to get attention and then hurts himself.”

The basis of this insanity lies less in O’Brien’s Lampoon days than it does in his time spent studying with the Groundlings, a prestigious Los Angeles improv troupe. “He’s the funniest guy on the planet,” says O’Brien’s close Friend and fellow Groundling, Lisa Kudrow. “For a long time when he was writing on Saturday Night Live, I would yell, ‘You’re there, you’re right there. Why don’t you just get on the show? It’s insane.’ But he was very firm in saying that people see you as either a writer or an actor.”

Which is both true and false. Just as O’Brien was not plucked against his will to be on television, he was also cagey enough to limit his ego to areas in which he could thrive. He wanted the Late Night job very badly. He has always considered himself happiest when performing but was content on the sidelines, waiting for the right vehicle. “I was working at William Morris and had access to the confidential e-mail when it was announced that Lorne Michaels was given the Late Night time slot,” says Jane O’Brien. “I called Conan and told him. I just knew it was his slot.”

I always joke that I’m the middle child screaming out for attention, and that’s what this show is about,” says O’Brien. “You make that joke, and you realize it’s rooted in something.”

For Conan O’Brien, the screaming began in Brookline, Mass., just outside of Boston, where he grew up as the third of six children born to his father, a doctor, and his mother, a lawyer. It was a close, Irish-Catholic family where jokes and teasing were valued currency.

“Comedy is a great passive-aggressive tool,” says O’Brien. “In my family, we didn’t really yell at each other. I love my family, and I love my parents, but I’m pretty passive aggressive, and I think we all are. I was halfway through my 20s when I realized that when people are unhappy with other people, they actually just tell them. I’m still stunned by that.”

It was a childhood defined by outward success but inner awkwardness and anxiety. O’Brien hated school, ultimately excelling because he saw it as something to which he must apply himself. He was overly earnest and, from the fourth grade on, considers his boyhood unhappy. He describes himself in the school cafeteria as “without a country” – he was not quite a regular with the athletes, the chess-clubbers or the wise-asses. “I didn’t really know what I was,” says O’Brien. “Some kids know who they are. To be brutally honest, I just didn’t. It went on quite awhile in my life. Even into my 20s.”

What O’Brien did know was that he was funny. “Comedy is defense mechanisms on overdrive,” he says. Those initial laughs helped steer him toward show business. Unfortunately, it was show business circa 1920. He wrote short vaudeville-style plays that he and a friend performed for his school, and he begged his parents to let him take tap-dancing classes until they found Stanley Brown, a protégé of Bill “Bojangles” Robinson, and O’Brien began lessons, too embarrassed to tell other kids but absorbed enough to continue for a couple of years.

“I had these very antiquated ideas of what an entertainer was,” says O’Brien. “You don’t have to know how to tap-dance. Tony Danza thinks you do, but you don’t have to know how to be a tap-dancer today. I used to go to these lessons. Just a group of young black kids and this skinny white kid with bright orange hair and his tap shoes in a box.”

And then O’Brien abruptly gave up his aspirations of soft shoes and snappy lines. Puberty was on its way, and as a neurotic in training, he needed to take serious stock of his future and career. Clowning around was strictly an amateur activity to be confined to the neighborhood or family dinner table. And so he did what he has always done: He worked. He devoted himself to school, ultimately becoming the Brookline High School valedictorian and shipping off to Harvard.

“I just assumed I’d become a lawyer or something serious,” says O’Brien. “I was kind of a serious guy.”

Instead he began writing for the Lampoon, the famous humor magazine tucked within the Harvard campus, itself a large brick bastion of unfunniness.

“I fell into it without trying,” says O’Brien. “I just liked to write funny things. And here were these semi-adults taking what I did seriously. It was the biggest thing that had happened to me in my life. It’s very hard to explain, but it was a very powerful thing. And then I got to edit the magazine two years in a row. That’s when I realized I wanted to do this with my life.”

O’Brien parlayed the position into tuxedo-clad spots emceeing campus events, eventually graduating to his post-college jobs writing for Not Necessarily the News, Saturday Night Live and The Simpsons.

“People act like it was just handed to him, and that couldn’t be further from the truth,” says Jane O’Brien. “He has always had a fierce direction and a fierce ability to do the work necessary to achieve a goal.”

Her brother Luke, a lawyer in Boston, concurs.

“I don’t even know how to resolve the two sides of him,” says Luke. “He was always joking and teasing our sisters. But he was also so hard-working. He was always good at saying, ‘Here’s something I want to do. I can’t do it now. How do I get to where I can?'”

His “Batman” Thing
Part 1

I maintain that the television series Batman is one of the most brilliant pieces of American art in the last 30 years,” says Conan O’Brien. When he was at Harvard, Burt Ward was invited to lecture about his role as Robin on Batman. According to the ads, Ward was bringing the original Robin costume, said to be valued at $500,000.

O’Brien: “So Burt Ward gave an interview to the school paper and sounded really pompous. We knew we had to do something.”

That something, as it turned out, involved O’Brien and a friend procuring security-guard uniforms.

“We went up to him and said, ‘Hello, Mr. Ward, the dean is worried about the safety of the costume,'” continues O’Brien. “He didn’t question for a second that the dean of a major university would dispatch guards for the Robin costume. He was like, ‘Excellent, I thought someone would be by.'”

During a post-lecture question-and-answer session, another friend stood up in the auditorium, dressed as the Penguin – despite the fact that he was behaving more like the Riddler – and asked, “When is a costume not a costume? When it’s stolen.”

O’Brien: “And just then we had someone turn off all the lights like in a bad movie. But, of course, in the movies it’s pitch-black, and here it’s really just a little dimmer. Which is an important thing to know for anyone out there contemplating a crime. So it gets grayish brown, and we grab the costume and take off.”

A chase ensued, with O’Brien and Co. eventually escaping to a hide-out where they took turns phoning up Burt Ward and snapping pictures of one another dressed as the caped crusader’s sidekick. O’Brien and his friends were in hysterics. Burt Ward was less than amused.

“I love in life when people act like you think they would,” says O’Brien. “He was on the phone going, ‘That costume better be returned or you’re in big trouble, mister. You’re not going to get away with this.'”

O’Brien laughs – you know the sound – and continues: “We eventually got it back to him, but it was not worth $500,000. If you went to his car and jimmied open the trunk, there’d be like 10 more there. Like he’s always giving them to girls.”

The moment you walk into Conan O’Brien’s apartment, you’re hit with a series of disclaimers: It is a mess because he has just returned from vacation; half the furniture is not actually his – he’s subletting; he knows the small pencil drawing of him hanging on the wall looks eerily like Eddie Munster, but what are you going to do? It was sketched and signed by Tony Bennett.

O’Brien grabs some beers from the fridge and settles in next to his girlfriend, Lynn Kaplan. The pair (she is a talent booker on Late Night) have been dating for three years and over the summer began living in sin in this sparse but elegant apartment with enormous windows. The building itself is less a civilian dwelling than a supermodel dormitory – Linda Evangelista lives next door; Cindy Crawford is down the hall – and O’Brien confesses to being unsure of proper celeb-to-supermodel etiquette.

“What am I supposed to do?” he asks, leaning back in his chair, sipping a beer. “Am I required to say something to these people?”

While this is a beautiful location to play out one’s personal life, O’Brien has little time for such a distraction. It is almost as if he doesn’t want to bother existing outside of the show. Friends talk of his confidence in the face of cancellation, but insecurity floats beneath the surface, suggesting that while he is overjoyed to have the show, he borders on being apologetic. He works until at least 9, even on nights when there is little for him to do.

“I was a hard-working guy who was intense about comedy and his career before I did this,” says O’Brien. “And this is that times three or four. I cannot imagine ever giving to anything else the way I do this.” He pauses. “I worry about having kids and doing this.”

He has spent time in therapy, hoping to better deal with what he calls “recurring habits of depression and beating up on myself.” It’s just that nothing is as real to him as the nightly hour of make-believe he lords over.

“It’s a sickness,” O’Brien says, “There are times where we’ll do a piece and I know that there are even hardcore fans who didn’t see it. It breaks my heart. I was a big fan of Late Night With David Letterman in the ’80s, and sometimes weeks would go by, and I wouldn’t see it. And that kills me.”

O’Brien laughs – not so much the sound you are used to but something sadder – and shakes his head: “We put in so much effort, and we think about it and work so hard. It’s on at 12.35 at night.” He laughs again. “There’s times I wish I could just come out and talk about fruit that I bought at the market and then have Andy sit on a stool and sing a song.”

The good news is that slowly, O’Brien is taking steps toward living a life outside the NBC studios. He just bought a weekend place in Connecticut – “Nothing crazy or anything,” he says – and confesses to being a sucker for virtually any movie, especially violent ones and documentaries.

Back in supermodel central, O’Brien gets antsy, grabs his beer and stands to host a tour of the apartment. He walks down the hallway, steps over an unpacked suitcase and scales the stairs to rummage through the second floor’s book selection. He holds one in the air.

“This is it,” he says, “one of the few laugh-out-loud novels I’ve read. Go ahead, borrow it.”

No, really, but thank you.

“Seriously,” says O’Brien. “Just get it back to me.”

He hands over the book, Masters of Atlantis, by Charles Portis, and walks downstairs for more show and tell, this time unpacking the prized Gretsch guitar he recently purchased. It is one of the few indulgences he has allowed himself (he still drives his 1991 Ford Taurus, for instance), and it is obvious he takes great pride in it, ultimately placing it carefully back in its case like a father tucking his child into a crib.

O’Brien distractedly saunters back into the hall. It is getting late. There is work to obsess over tomorrow, so O’Brien shows his guest to the door and suggests taking the stairs to better appreciate the old building’s architecture. The next day, when he realizes the book he has loaned was left behind in his apartment, Conan the librarian sends it along by messenger.

His “Batman” Thing
Part 2

As an adult, O’Brien once dragged his entire family to a Batman convention to meet the show’s star, Adam West. So when O’Brien says, “I never really had big aspirations toward working on sitcoms,” you know there is one notable exception. The title was Lookwell. In 1991, O’Brien and fellow Batman obsessive Robert Smigel, his friend from SNL, made a pilot for NBC. Of course, it starred Adam West.

Smigel: “We were so happy. We had to fight so hard to get Adam West to be the guy.”

O’Brien; “He played an actor named Ty Lookwell who had a hit show in the 70s, a Quinn Martin production. And when he had the show, he got to go to all these law-enforcement luncheons, and it went to his head a bit. So he thinks he can solve crimes. He carries around a badge that’s encased in a Lucite block and shows it to people. He wears turtlenecks. He’s a little down on his luck but just gets by. At the time I thought Adam West was just right.”

The show did not get picked up by the network.

“There’s actually a little cult following of the pilot episode,” says Smigel. “That’s kind of nice. I’m really proud of it. But I was so disappointed that we didn’t get to revive Adam West’s career.”

You wouldn’t imagine that a man who makes nearly $2 million a year would have a giant gherkin pickle in his office, but there it is, propped against the wall, just behind an amplifier, piles of gadgets and an enormous painting of Abraham Lincoln on his deathbed.

The entire Late Night headquarters has the feel of a freshman dorm where the hall monitors have been assassinated. Shouts filter up and down the horseshoe-shaped corridors; Andy Richter, who is fond of saying, “If I play my cards right, I won’t have to say a word tonight,” strolls around barefoot, wearing shorts and a T-shirt; in the conference room there is a stack of TV Guides with O’Brien on the cover; some of them have been defaced to make him, among other things, a pirate, a woman, a devil and a member of Kiss.

It’s doubtful that so much brainpower has ever come together to produce something so silly. O’Brien was an American-history and -literature major at Harvard. His thesis was on Flannery O’Connor and William Faulkner – “The least funny thing I ever wrote,” he says. His head writer, Jonathan Groff, is a five-time Jeopardy! champion. “Our comedy is not real, in a way,” says Groff. “It’s not ironic and winking. Letterman did this show for 11 years and blew past so many boundaries. It’s been kind of fun for us to go back and say, ‘What if we don’t deconstruct this?'” Which is a better way of saying that Late Night strives to keep up the walls between viewer and performer. It also attempts to stay away from topicality. Instead of Kathie Lee Gifford jokes, for instance, you get Celebrities in a Box, a segment in which Nipsey Russell and Hair Club for Men president Sy Sperling were locked in a box. Using time-lapse photography, the progress of their acquaintance was monitored.

“Conan’s humor was never insensitive, which is what I always admired about him,” says Lisa Kudrow when asked if O’Brien always tended toward the surreal. “He didn’t have to destroy anyone in order to be funny.”

The show still considers itself edgy; it’s just that O’Brien and his writers try to remain true to their initial vision for Late Night, creating a world and environment that are decidedly other. It is a direction plotted by O’Brien and Smigel with the help of original writers Louie C.K. and Dino Stamatopoulos, all of whom, surprisingly, have no ties to Harvard Lampoon. To date, in fact, Late Night has hired only one Lampoon alumnus.

“I have such mixed feelings about the Lampoon,” says O’Brien, sitting on a couch in his office. “On the one hand, it was such a powerful thing to me. But it’s pre-professional now. It’s Humor Incorporated. When I got this show, people probably thought I was going to open up some secret book and fill the staff with the Harvard Lampoon, and I didn’t do that.”

O’Brien stands and walks out of his office to introduce various scruffy members of the writing staff, obviously pleased with the ragged assemblage of comic misfits and performers that stalks the halls. It is a type of Wild Bunch, perhaps less homicidal but equally willing to try anything, all equally defensive about perceptions that the show has suddenly, miraculously sprung from the ashes.

“I’m sick of hearing about how the show’s gotten better,” says Richter matter-of-factly. “Yeah, from the first six months. But it’s been a pretty good show for a couple of years now. Duh.”

Richter grins and follows O’Brien as he heads downstairs to the studio, where he slips out of his jeans and dons a suit for a lighting test on the new set. O’Brien proudly remarks that back in the days of SNL and The Simpsons, he was a guy who sat around all day wearing T-shirts and thinking of off-the-wall ways to make people laugh, and now he is that same person – only for one hour a day he is required to play dress-up.


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