After graduating as valedictorian in 1981, O'Brien entered Harvard University. He lived in Holworthy Hall during his first year with future businessman Luis Ubiñas and two other roommates, and in Mather House during his three upper-class years. He concentrated in History & Literature, and graduated "magna cum laude" in 1985. O'Brien's senior thesis concerned the use of children as symbols in the works of William Faulkner and Flannery O'Connor. During college, O'Brien briefly played drums in a band called the Bad Clams, was a writer for the "Harvard Lampoon" humor magazine, and developed a spoof of the video game ' in which the Boston Celtics play against a classical ballet troupe. During his sophomore and junior years, he served as the "Lampoons president. At this time, O'Brien's future boss at NBC, Jeff Zucker, was serving as president of the school newspaper "The Harvard Crimson".