It’s not hard to believe that the author of this thesis also catapulted the “masturbating bear” character to fame on national television when one reflects upon the work he did in his other writing outlet: the Harvard Lampoon, a semi-secret Sorrento Square social organization that used to occasionally publish a so-called humor magazine.
By sophomore year, O’Brien had been elected Lampoon President—a role that suited him beautifully, according to Widmer, who said O’Brien had “the body of Abraham Lincoln and the head of Martin Van Buren.” He became the first leader in the magazine’s 134-year history to reign for two terms.
“The whole job is to try to strike a balance between trying to make as many jokes as possible and appear as non-caring as possible, and yet caring enough to get things done,” O’Brien said in his 1985 profile.
Often, O’Brien’s actions spoke louder than words.
One day in 1984, O’Brien and a few ’Poon affiliates masqueraded as security guards while a decoy in a penguin costume made a grand entrance into a Science Center hall where actor Burt Ward was displaying his Batman costume. According to Widmer’s version of the tale, the penguin unleashed the code words:
“Riddle me this, boy wonder: when is a security guard not a security guard?”
At that moment, the boys hit the lights and dashed towards the costume. But there was one problem.
“We meant to turn off all the lights in the Science Center, but they only have dimmer switches,” Widmer recalled. “It was kind of a bungled prank.”
In the ensuing chaos, O’Brien managed to snatch the costume away.
“I just remember looking at his legs running up the Science Center stairs as I was being tackled by the Dunster House Film Society,” Widmer said.
The legacy of absurdity has certainly not dried up in the Lampoon Castle.
Outgoing Lampoon Ibis Benjamin U. Steiner ’10-’11 said that “Brother O’Brien” still inspires ’Poonsters.
“Additionally, if we say his name at the Hair Cuttery we get a free bottle of styling mousse,” he wrote in an e-mail, in typical Lampoon jest.
STAR ON THE RISE
After graduation, O’Brien ventured west and snagged jobs penning Saturday Night Live sketches and Simpsons episodes. When he took over David Letterman’s Late Night slot, Reiff said O’Brien’s “emotional intelligence” shone.
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