Conan O’Brien‘s origin story is almost purposefully ridiculous. This man began by writing a senior thesis on William Faulkner and Flannery O’Connor. Over the course of three decades, he would perfect the art of awkward self-deprecation and surreal physical comedy. The thesis, Literary Progeria in the Works of Flannery O’Connor and William Faulkner, looked at how children are used as symbols in serious American literature. It’s not exactly what you would expect from a guy who used to slow-dance on cable television with a bear that was masturbating.
O’Brien was born in Brookline, Massachusetts, on April 18, 1963, into a family that valued intelligence. His father taught at Harvard Medical School and practiced medicine. His mother practiced law and was a partner in a Boston law firm. Ambition didn’t need to be explained or encouraged when I was growing up in that setting. It was just the house’s air. By the time O’Brien arrived at Brookline High School, he was already working as an intern for Congressmen, running the school newspaper, and winning a national writing competition with a short story titled “To Bury the Living.” In 1981, he graduated as valedictorian.
What came next was Harvard, where I majored in literature and history, graduated with honors, and served as president of The Harvard Lampoon for two years. It’s worth taking a moment to consider that final role. One of the nation’s oldest humor publications, The Lampoon is run by more than just students at Harvard. It serves as a testing ground. For more than a century, future writers, showrunners, and satirists have gone through those offices. Conan took the lead rather than just taking part. He may have learned how to read a room and trust his own comedic instincts from this experience more than from any classroom.
He seems to have never completely let go of his academic background. The structural discipline needed to write a tight sketch or a late-night monologue is similar to the literary precision needed to analyze Flannery O’Connor. His work on The Simpsons, especially “Marge vs. the Monorail” and other episodes, demonstrated a writer who was aware of timing, subversion, and the absurdity that can be found in everyday circumstances. These are not spontaneous instincts.
Not everyone became famous right away after graduating from Harvard. After relocating to Los Angeles and enrolling in The Groundlings’ improvisation classes, O’Brien wrote for a forgettable sketch show before landing a spot on Saturday Night Live in 1988. Far from the prestige of a magna cum laude degree, the work was tedious and unpredictable. A Harvard man in his late twenties probably caused some family members to take notice when he wrote punchlines for a late-night sketch show. Nevertheless, it’s difficult to ignore the fact that he persisted in writing and honing a skill that his education had enabled him to recognize but was unable to produce for him.
He was chosen by Lorne Michaels to host Late Night in 1993, which was a huge risk for a writer with very little on-screen experience. The initial reviews were harsh. Critics weren’t persuaded. However, O’Brien outlasted the skepticism thanks to his sincere intellectual curiosity and total willingness to look stupid on national television. For sixteen years, he occupied that position.
He returned to Harvard in 2025 to give the commencement speech. The former valedictorian, now inducted into the Television Academy Hall of Fame and the recipient of the Mark Twain Prize, stood in front of a new class of exceptional students. It’s still unclear if any of them really understood what they were witnessing: a man who wrote jokes about a monorail using one of the best educations in the world.
That is either a master class or a waste. As his career develops over the years, it clearly resembles the latter.
