In 1983, Borowitz was back on campus and set to attend a black tie event, but realized when he got to his hotel that he had forgotten to bring his tuxedo pants with him. And due to his extended frame, he had difficulty remembering someone who would have a spare set of pants that would fit him.
“All I could think of was Conan O’Brien, because Conan was on the Lampoon, and they have black tie events on Thursday nights, and Conan is about my height,” Borowitz says.
And although O’Brien—who was also president of the semi-secret Sorrento Square organization that used to occasionally publish a so-called humor magazine—could not be reached to confirm the story, Borowitz claims that he provided some less-than-ideal pants.
“In those days Conan was so skinny,” Borowitz says. “He was so skinny I could barely fit into Conan O’Brien’s pants...It was the tightest fit. It was like wearing a leotard basically.”
Despite O’Brien’s lanky frame, Borowitz credits the late night talk show host for encouraging him to take more risks in his life.
“I got to say that Conan, I think, really was influential in showing that you really do have to follow your own path regardless of whether others think it’s a good idea,” Borowitz says.
After establishing himself through his work as a writer for the hit TV show The Fresh Prince of Bel Air, Borowitz left the security of Hollywood in 1998.
Now he has his own website, has authored four books, and makes regular appearances on CNN’s American Morning and in stand-up—and Borowitz still attributes part of his comedic inspiration to his undergraduate years at Harvard.
While a student, Borowitz made a name for himself as a writer, a director, and an actor in several plays, in addition to his involvement with the Harvard Lampoon. And while many of his exploits helped to garner him notoriety around campus, some of the press he encountered was not quite so positive.
In the summer before his senior year, Borowitz and the Lampoon sent out a special prank issue of The Crimson to all of the incoming freshmen, in which they described college life as one filled with sex, drugs, and rock and roll. The description was so vivid and disconcerting for many of the prefrosh and their parents that University Hall was flooded with angry phone calls and threats of transfers to Yale.
The Harvard administration did not take kindly to the prank and pressured Borowitz to reveal the name of the source who provided him with incoming students’ addresses.
“For about six months of my senior year, they were kind of playing ‘crime and punishment’ with me, trying to figure out how on Earth I got ahold of all of these addresses, which was just an incredibly top secret document, like the codes that NORAD has to launch nuclear weapons,” Borowitz says. “But they never cracked me. I was sort of like Deep Throat. I just stuck to my guns.”
As John F. Bowman ’80—also a former Poonster—recalls, such behavior was not unusual for Borowitz.