The Conan We Knew

Renowned talk show host Conan C. O’Brien ’85 was a loyal friend, a literary scholar, and two-term Lampoon President during his Harvard days

Courtesy of Eric Reiff

“Book checker, book checker, please check my book! Open my bag, please take a look—Book checker, book checker, please check my book, Oooooh book checker!”

The long legs of 18-year-old Conan C. O’Brien ’85 bounded across Harvard Yard, red hair bobbing up and down, his impeccable mock cockney accent ringing out into the night.

O’Brien’s Holworthy 16 and later Mather House roommate Eric B. Reiff ’85 strode alongside him, laughing aloud and thinking to himself, “That’s unusual.”

“Most of us are not walking around making up musical comedies in our heads when we’re 18 or 19-years-old,” Reiff said.

The subject of O’Brien’s musical ode was an elderly gentleman who worked the desk at Lamont Library in 1985. O’Brien befriended the book checker, always engaging him in hilarious banter on his way out of the library, according to Reiff.


“Conan does not have an elitist bone in his body,” Reiff said. “He is as interested in what the book checker says as what some eminent professor says—and is open to the idea that the book checker might be funnier.”

From running the Lampoon, to penning Saturday Night Live sketches, to hosting Late Night with Conan O’Brien for 16 years, and finally to his brief stint as host of The Tonight Show, Reiff said there are things about O’Brien that have never changed: keen powers of observation, a killer range of spot-on impressions, and a genuine interest in everyone he meets. And, of course, that hair.


The third child of six in a big Irish Catholic family, O’Brien grew up in Brookline, Mass. with father Dr. Thomas O’Brien, a physician and Harvard Medical School professor, and mother Ruth O’Brien, an attorney. The O’Briens were incredibly “gracious and generous,” Reiff said, and frequently opened their home to their son’s roommates.

“It was this big, rambling, wonderful family house filled with wonderful family people and a loving mother and a loving father—it was almost the kind of family you dream of having but don’t think can be found anywhere,” said O’Brien’s former roommate, Ford Foundation President Luis A. Ubiñas ’85.

According to Ubiñas, O’Brien’s middle-child status forced him to cultivate two important skills: watching and communicating.

Indeed, the other member of the Lamont book checker’s “two-person admiration society,” O’Brien’s friend Edward L. Widmer ’84, said that “with Conan, every single thing over the course of the day is an object of humor and observational comedy and wordplay—it was just always great to be around him.”

After graduating as valedictorian from his class at Brookline High School, O’Brien arrived at Harvard full of contagious energy.

“My first impression was that he was incredibly tall and incredibly red—he seemed seven feet tall to me and that giant shock of unruly red hair was unlike anything you’ve ever seen,” Ubiñas said.

His height still resonates with Lampoon buddies 25 years later.


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