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Conan O'Brien's Three-Year Overnight Success

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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?'"

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