Fifty-five years ago today, Buddy Holly’s plane crashed and claimed the lives of three of the most up-and-coming rock and roll musicians the world knew to that point. But before Buddy Holly died on that plane with Richie Valens and J.P. “The Big Bopper” Richardson on February 3, 1959, he went on a buying spree, picking up cars and motorcycles just as iconic as the music he was playing.

1958 Chevrolet Impala

As Buddy Holly and the Crickets began to attain a level of success, Holly wanted a car. Back in a time when record sales equaled a fair bit of cash, a 20-year-0ld Buddy Holly went to Meadors-Stewart Co. in Clovis, New Mexico and laid out the funds for a 1958 Chevrolet Impala, in Cay Coral Metallic.

Holly loaded the car to the gills with the top-of-the-line 348-cu.in. V8, twin antennas and mirrors. Meadors-Stewart also equipped the Impala with a set of gold 50th anniversary wheel spinners and whitewall tires to match the white roof and body stripe, painted fender skirts and a coral interior dress up kit.

In 2010, Barrett-Jackson originally offered a ’58 Chevy Impala, purporting it to be Buddy Holly’s original car. But days before the auction, the company pulled it off the docket, claiming that it was “unable to obtain satisfactory information to resolve the issues that were raised during the company’s investigation.”

1959 Ariel Cyclone

While he was into cars, Holly also had a fascination with motorcycles. Waylon Jennings — Buddy Holly’s bass player, and the guy who fatefully gave up his seat on the plane that killed Buddy Holly — tells a story about Buddy Holly purchasing a 1959 Ariel Cyclone. The story is on the blog, Saving Country Music:

“They loved Marlon Brando in “The Wild One,” and when they got to Dallas…they decided on the spur of the moment to buy motorcycles and drive back home on them.” Waylon recalled. “They took a cab into the city and walked into a Harley-Davidson shop. They had their eyes on a trio of 74-inchers, but the proprietor didn’t think they had any money and treated them like a bunch of bums. ‘Hell, you boys couldn’t even begin to handle the payments on that.’

“Then they went over to Miller’s Motorcycles, which specialized in English bikes. There, Joe B, and J.I. (Allison) bought a Triumph each, a TR6 and Thunderbird, respectively, while Buddy picked out a maroon and black Ariel Cyclone, with a high compression 650cc Huntsmaster engine. They paid cash, bought matching Levi jackets and peaked caps with wings on them, and rode home through a thunderstorm.”

Holly’s father ended up keeping the motorcycle until 1970. In 1979, for Waylon’s 42nd birthday, the two remaining Crickets — Joe B. Mauldin and J.I. Allison — tracked down the 1959 Ariel Cyclone, bought it, and had it hand delivered to north Texas where Jennings found it sitting there in the middle of his hotel room after walking off stage that night.

“What else could I do?,” Jennings wrote years later. “I swung my leg over it, stomped on the kickstarter, and it burst into roaring life. First kick. It was midnight, and it sounded twice as loud bouncing off the walls of that hotel room. I knew Buddy wouldn’t mind.”

Here’s some footage of Holly on the bike: