The private $7,500 letter that John Lennon wrote to Waylon Jennings

In 2014, Guernsey’s Auctions sold a letter, only a handful of lines long, for $7,500.

It was part of a liquidation of over 2,000 pieces from Waylon Jennings’ estate. The country singer’s vast collection boasted lots of curiosities, but the handwritten note from none other than John Lennon himself proved to be one of the most interesting.

In Jennings’ biography, the letter was briefly mentioned. The 1996 book gave no context for their relationship, simply stating: “A Beatle writes”. It created confusion, given the two were bona fide stars, but musically worlds apart. Jennings was considered one of the pioneers of the outlaw movement in country music, having rallied against the Nashville establishment that wound up dictating what country “should” sound like. Whereas Lennon was a commercial favourite, his success with The Beatles was so massive it’s almost too obvious to state.

Despite their apparent differences, the two artists had a lot in common. Buddy Holly was a significant shared influence, given his evident hand in the early Beatles sound. Lennon said in Anthology that Holly was “the first one that we were really aware of in England who could play and sing at the same time – not just strum, but actually play the licks”. 

Jennings himself could testify to Holly’s ability, given he had spent time playing bass in The Crickets alongside the bespectacled icon. He was even set to join him on the plane that crashed on The Day the Music Died, but he gave up his seat to The Big Bopper.

This incident had a lasting impact on the country star, opening him up to care for all of his fellow creatives. But as Jennings revealed in a 1996 interview, when it comes ot Lennon, the two had never imagined they’d get on. “I met John Lennon, and we were cutting up and everything at one of the Grammy things,” he said. 

John Lennon - 1972 - Musician - The Beatles
John Lennon performing live in 1972. (Credits: Far Out / Alamy)

Adding, “And I said, ‘Man, you’re funny. I didn’t know you were funny,’ I said, ‘I thought you were some kind of mad guy or something like that.’” In itself, that’s a hilarious thing to say to somebody, let alone the world’s leading star of the moment.

Lennon’s dry response was: “Listen, people in England think you shoot folks.”

Essentially, when Jennings was recording early on in his career, a disdain for session players playing pickup notes led him to bring out a Colt Buntline revolver and declare, “The first guy that I hear use a pickup note, I’m going to shoot his fingers off!”

Reports started flooding through the British music press that he’d brought a gun to a session, but for all of his outlaw reputation, he and Lennon got on great. “Twas good ta meetya!” Lennon wrote in the letter, which seemed to reference an unreleased mystery song that Lennon had invited him to try out: “[Sic] I should have released it as a single myself, but I left it to late… but it aint for someone else…”

From the clumsy misspelling of Jennings’ name: “Dear Wayland (sorry about that),” to his inclusion of his Liverpudlian twang in his writing, the letter remains an intimate look at their unlikely friendship. And the price that it fetched at auction is proof of how every word they have spoken has been revered by the masses ever since they graced the world stage.

It’s almost exactly 45 years since John Lennon passed away. Here’s a letter Lennon wrote to Waylon Jennings after they’d met in 1975.

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