Outlaw country singer Waylon Jennings owned a vintage motorcycle that had previously belonged to his close friend, rock `n’ roll star Buddy Holly.
Jennings was supposed to have been with Holly, Ritchie Valens and J.P. “The Big Bopper” Richardson when the crooners were killed in a 1959 small-plane crash that became known as “the Day the Music Died.”
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Two decades later, members of Holly’s band, the Crickets, tracked down the red Ariel Cyclone and gave it to Jennings as a birthday gift that he kept in his living room until he died in 2002.
The bike is among thousands of items that Jennings’ estate is putting on the auction block Sunday online and at the Musical Instrument Museum in Phoenix.
Jennings, known for his black cowboy hat, recorded 16 No. 1 country singles over his decades-long career. His hits include the theme from the “Dukes of Hazard,” a television show that he also narrated, and the Willie Nelson duet “Mammas Don’t Let Your Babies Grow Up To Be Cowboys.”
Something literally connected to Nelson also will be up for sale: his braids.
The signature locks were presented in 1983 as a gift to celebrate Jennings’ sobriety at a party thrown by Johnny Cash, said Arlan Ettinger, co-founder of Guernsey’s, the New York City-based auction house running the sale.
Jennings teamed with Nelson, Cash and Kris Kristofferson to form the country super group, the Highwaymen. Their original contract, signed by all four members, is also up for sale.
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Ettinger wouldn’t estimate how much the items would go for.
“It’s very hard to say, particularly when something is made valuable by virtue of its history,” Ettinger said. But the motorcycle, “I certainly think it’s going to bring hundreds of thousands of dollars.”
Jennings’ widow, singer Jessi Colter, who lives in Arizona, provided the items for sale, which also include guitars, handwritten song lyrics, a letter signed by John Lennon and a boxing robe worn by Muhammad Ali, Ettinger said.
The singer lived in suburban Phoenix when he died in 2002 at age 64 of diabetes-related health problems.
Ettinger said he had considered holding the auction in the country music capital of Nashville, Tennessee, but Colter said her husband loved Arizona more than most places.
“He felt most at home here,” Ettinger said.
Some auction proceeds will benefit Phoenix Children’s Hospital per Colter’s wishes, Ettinger said.