Brookline babylon

Cult leader Charles Manson. Serial killer Jeffrey Dahmer. Essayist John Hodgman. What was it in the tap water of Brookline, Massachusetts, that led this town west of Boston to spawn such infamous progeny? It was from this fetid cesspool that Conan O’Bryan emerged in 1963, born out of wedlock to a Welsh bootlegger and his jam maker bride.

With Prohibition having ended several decades earlier, the elder O’Bryan’s bootlegging failed to bring much money into the home. While Conan’s mother doted on her only child, his father’s failed attempts to enter legitimate business as a phrenologist only furthered his bitterness and mood swings.

Socially awkward and cursed with the physique of a malnourished undertaker, Conan O’Bryan retreated to a fantasy world, imagining his bedroom as a talk show set, always with the same two cardboard cutouts serving as his guests: Winston Churchill and Joyce DeWitt.

Fate intervened when the high school senior O’Bryan found himself behind local mob boss Whitey Bulger in line at Beefsteak Charlie’s all-you-can-eat salad bar. O’Bryan warned Bulger to avoid the Thousand Island dressing for gastrointestinal reasons. Feeling indebted, Bulger asked O’Bryan what he could do to repay the favor, and O’Bryan suggested, “Could you get me into Harvard?”

Two phone calls and an unsolved arson later, O’Bryan received an acceptance letter from Harvard University, followed up shortly by a weeping, terrified admissions officer begging O’Bryan to enroll. O’Bryan agreed, and in a confused attempt to hide his family’s Welsh bootlegger origins, “Anglicized” his name to O’Brien.

Young Conan at Beefsteak Charlie's