“I have to stand on a chair when we kiss,” his friend Mark R. Ganem ’85 joked in an e-mail to The Crimson.

But did his peers know he was destined for stardom?

“I always thought that of all the talented people I knew in college, Conan was the most likely to appear on the cover of Time magazine—I just thought it would be for mass murder,” Ganem continued in jest.

In a Commencement issue for the graduating class of 1985, The Crimson called O’Brien the class’s “pre-eminent jokester” and predicted big success for the “gangly, freckle-faced jester.”

But O’Brien almost didn’t get the chance to cultivate this glorious reputation—all because of innocent curiosity and a bag of Twinkies.

MISCHIEF MAKER

One question plaguing O’Brien and his roommates during freshman year was whether or not Twinkies were combustible.

In searching for the answer, the boys managed to set a garbage can on fire.

“For fear of burning down all of Holworthy, we threw the flaming can out the window, where it promptly landed at the foot of one of the resident deans—fortunately we were all such good guys that no one wanted to kick us out," Ubiñas said.

Had O’Brien been expelled, he would have had fewer chances to perfect his imitation skills, which have served him well in the world of late night talk shows. Friends say O’Brien mimicked everyone from professors to politicians.

Once, O’Brien and Reiff attended a convention to support Evelyn F. Murphy, who was running for Mass. lieutenant governor against John F. Kerry. Kerry himself strolled over to the Murphy T-shirt clad boys and started persuading them to shift their loyalties in a “very high school politics kind of way,” Reiff recalled.

“Conan thought this was hysterically funny,” Reiff said. “He loved to talk about it and reenact it—he’s a great mimic and he noticed things other people didn’t notice.”

WORK HARD, PLAY HARD

Reiff said that if there was one thing in O’Brien’s life that was not a joke, it was his schoolwork.

A History and Literature concentrator, O’Brien crafted a senior thesis entitled “The ‘Old Child’ in Faulkner and O’Connor.” The 72-page typewritten work argues that the New South’s emerging identity is manifested in the literature of William Faulkner and Flannery O’Connor via the motif of children that age too quickly, a phenomenon O’Brien termed “literary progeria.”