Conan O’Brien’s Hilarious Night in Jail at College

Conan O’BrienAmerican institution and a loved public figure. Harvard University is where the famous talk show host and podcaster was educated. Did you know that he once spent a night in prison during his college years? Here’s the funny story.

Conan O’Brien: Gentleman Of Harvard

The pride of Brookline, Massachusetts, O’Brien graduated valedictorian of his high school class and was admitted to the 1985 class at Harvard University. He majored in History & Literature and graduated magna cum laude. Writing his thesis on William Faulkner and Flannery O’Connor was only part of his workload; he moonlighted as a writer for the Harvard Lampoon. Greg Daniels was his future co-creator. The Office.

Naturally, O’Brien engaged in all manner of tomfoolery whilst learning in Cambridge. Once he pranked Bill CosbyInventing a lifetime achievement prize and telling Cosby he had to visit in person in order to get it. Cosby did, where O’Brien picked him up not in a stretch limousine but his parent’s station wagon. Cosby was not awarded a lifetime achievement award but an old bowling trophy.

Go after his future boss

One butt of O’Brien’s jokes was the editor for the prestigious newspaper, The Harvard Crimson. When O’Brien attended, the editor was Jeff Zucker. This name may sound familiar as he was the President of NBC that chose Jay Leno over O’Brien in the 2010 late-night wars. 

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In College, O’Brien once broke into the Harvard Crimson office to steal an entire print run of the paper. Zucker Called the cops to him. “College pranks are supposed to be clever, but our rivalry with the Crimson had degenerated into us stealing something, Jeff calling the police, and the police making us haul it back,” O’Brien later told the New Yorker.

Pranking the Police

It’s one thing to mess with a rival paper, but messing with the state police is a whole other kettle of fish. The 2004 issue of Harvard MagazineAn impressive prank that might or may not have been performed was described. Legend says O’Brien and his LampoonThe group got some hard hats to wear and jackhammers for a few hours before hitting the streets of Boston. They tore up the pavement for a while before O’Brien called the cops. He claimed that the Boston police had been contacted by college students who were pretending to work as construction workers, and they were tearing up streets.

Here’s where the prank goes from needless to clever. O’Brien then called the Massachusetts state police and told them some college students were dressed as cops and hassling the local police officers. The staties followed the Boston cops soon after. Cops arrested the cops. Once the confusion subsided, O’Brien was sent to jail for one night.

This story could just be legendary. O’Brien declined to comment on “advice of counsel.” It’s no wonder a clever joke like this is in the repertoire of a comedy legend. O’Brien is currently developing a new show for HBO Max.

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