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Conan O’Brien is a self-described “insane Beatles fan,” so he was thrilled to get the chance to meet Paul McCartney. After O’Brien complimented McCartney for the majority of their conversation, the former Beatle jokingly offered him the opportunity to insult him. O’Brien responded with a barb that he hoped kept McCartney up at night.

Conan O’Brien complimented Paul McCartney on his pre-Beatles band

During a conversation with McCartney, O’Brien spoke glowingly about the “Golden Slumbers” medley. After a largely complimentary chat, McCartney offered the comedian a chance to insult him. O’Brien embraced the opportunity.

“He said, ‘Well, you’ve said some nice things to me. Maybe you want to even it out a little,'” O’Brien recalled on his podcast Conan O’Brien Needs a Friend. “‘Like, you’ve said some nice things, maybe you want to go the other way for the next comment.’ And I said, ‘Okay, you guys peaked with the Quarrymen. Everything after that was s***.'”

The Quarrymen was McCartney’s pre-Beatles band. John Lennon formed it in 1956, and it eventually became The Beatles. O’Brien hoped the comment stuck with him.

“He didn’t laugh. He looked a little surprised,” O’Brien said. “And then I knew to walk away, and I thought maybe — maybe — that’s gonna penetrate everything else he’s heard tonight. Maybe he’s gonna wake up at two in the morning and go, ‘Did that f***er say that I peaked with the Quarrymen?'”

McCartney did terribly in his first performance with the Quarrymen

McCartney’s work in The Quarrymen allowed him to play in a band with Lennon and George Harrison for the first time. It also brought him one of his first onstage embarrassments

“For my first gig, I was given a guitar solo on ‘Guitar Boogie,’” McCartney said in The Beatles Anthology. “I could play it easily in rehearsal, so they elected that I should do it as my solo. Things were going fine, but when the moment came in the performance, I got sticky fingers; I thought, ‘What am I doing here?’”

McCartney joined the group after they’d already been working together for a time. The existing members said his performance humiliated them.

“At first we were embarrassed, just really uncomfortable with what had happened,” drummer Colin Hanton said in the book The Beatles: The Biography by Bob Spitz. “John insisted on a certain degree of professionalism. And now the new guy made us look worse than the amateurs we were.”

Before long, though, McCartney began to thrive onstage. 

Paul McCartney, John Lennon, and George Harrison turned the Quarrymen into The Beatles

The Quarrymen eventually evolved into The Beatles. John Lennon’s wife, Cynthia, recalled the brainstorming session for a new band name.

“To fit with their changing image, the boys decided it was time for a new name,” she wrote in her book John. “We had a hilarious brainstorming session over a beer-soaked table in the Renshaw Hall bar, where we often drank.” 

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She said Lennon was behind the now-iconic name.

“John loved Buddy Holly and the Crickets, so they toyed with insect names,” she wrote. “It was John who came up with Beetles. He changed it to Beatles because he said if you turned it round it was ‘les beat,’ which sounded French and cool. They settled on the Silver Beatles.”