Conan O’Brien Joked About Frank Sinatra Beating Him With a Trash Can for Drinking Coca-Cola

Insisting he was telling a true story, comedian Conan O’Brien joked about how singer Frank Sinatra came to the Harvard Lampoon when O’Brien was president in 1983 and savagely beat him with a trash can when he realized O’Brien was drinking Coca-Cola from a coffee mug.

O’Brien recounted his college days in the early ’80s, sharing he didn’t drink or do drugs while attending Harvard. “I’m an incredible square,” he said on the Conan O’Brien Needs a Friend podcast.

“I never drank in college,” he added. “And then I walked in on some people who were doing cocaine. I opened the door and some guys I’ll never forget, they were wearing white tuxedo jackets like the evil kids do in a John Hughes high school movie. And they looked up and they said, ‘Hey, man, you want to do a line?’ And I said, ‘Thank you, but no. It interrupts the heart rhythm.'”

Conan O’Brien recalled working at the Harvard Lampoon

Comedian John Mulaney was O’Brien’s guest on the podcast and wondered if the rumor was true that he kept a huge tank of nitrous in college. “It is not true,” O’Brien said. “I did not. Was there a tank of nitrous at the Lampoon building? Yes. Was I the president of the Lampoon for two years in charge of things? Yes. Did I order the tank of nitrous? No.”

Conan O'Brien delivers his first monologue on June 1, 2009 on The Tonight Show
Conan O’Brien | Paul Drinkwater/NBCU Photo Bank

O’Brien added that he took his job as president of the Lampoon so seriously he insisted on wearing a three-piece suit. “I actually wore, like a vest,” he said. “I was such a square and then we’ve got these upperclassmen saying we’ve got nitrous coming in.” Adding, “I never did any of that. And I used to walk around with Coca-Cola in my glass.”

Frank ‘f***ing lost it’ when he realized Conan was drinking Coca-Cola

Mulaney said Sinatra hated it when people around him refused to drink alcohol. So he’d smell their glass to make sure they were drinking whiskey. That’s when O’Brien joked about Sinatra coming to the Lampoon and being unhappy with his drink of choice.

“He did come by the castle in ’83. The doorbell rang and I had a big coffee mug, but it had Coca-Cola in it,” O’Brien said. Mulaney continued painting the picture by dressing O’Brien in a top hat and tails.

“And I opened the door,” O’Brien continued with the joke. “And it was Frank Sinatra. He said, ‘Hey ring-a-ding-ding.’ And then he said, ‘What’s in the glass?’ And I said ‘Nothing but gin here, Frank.’ And he said ‘I got to smell it.’ And he smelled my glass. And he could smell that it was Coca-Cola, and he f***ing lost it.”

Frank Sinatra (or Jilly Rizzo) beat Conan O’Brien with a trash can

O’Brien topped off the story with a little beating from Sinatra. “This is a true story,” O’Brien insisted. “1983, February of ’83. And he lost it. And he was with Jilly Rizzo. Oh, man. His big bodyguard. And he said, ‘Jilly, show this leprechaun what we do.’ Mr. Sinatra is very disappointed in you. And he beat me with a trash can.”

O’Brien later explained that the trash can beating was done with mobster-like precision so that it didn’t leave a mark. “So that was the day that I was beaten …,” O’Brien concluded while everyone in the studio couldn’t stop busting out in laughter.

“It would be great if his true passion was not the blues and it was not the great American songwriting tradition. It was Ivy League humor,” O’Brien quipped.

RELATED: Conan O’Brien Thought an ‘Animal Crossing: New Horizons’ Room Was a Coworker’s ‘Cool, Creative’ Real House