Motorcycle Classics Blogs > Vintage Motorcycle Auctions and Results

‘Remembering Waylon’: A Motorcycle Auction Celebrating Waylon Jennings’ Life

Old photo of Buddy Holly's Ariel featured in the Remembering Waylon auction 

NEW YORK (August 20, 2014) – Guernsey’s Auction House will resurrect the aura of Outlaw Country megastar Waylon Jennings on October 5 at the majestic Musical Instrument Museum in Phoenix with an auction of more than 2,000 of the country legend’s personal belongings. The centerpiece of the spectacular collection is the limited edition 1958 Ariel Cyclone motorcycle that originally belonged to Jennings’ best friend and mentor Buddy Holly. The Ariel is beautifully preserved with just over 4,000 original miles, and has not been ridden in over twenty years, serving as a symbol of a pivotal time in American music history.

On May 13th, 1958, three young and newly successful musicians – Buddy Holly, Joe Maudlin, and Jerry Allison – found their way to Ray Miller's Motorcycle Shop in Dallas, Texas. They had conceived a style of music redefining America's tastes, combining Country, Pop, Rockabilly, and Rhythm and Blues into a new sound all its own.

Having just returned home from a world tour, Buddy Holly and the Crickets each bought new motorcycles to celebrate their hard work and good fortune. Joe Maudlin, the Crickets' bass player, immediately fell in love with a Triumph Thunderbird motorcycle. Jerry Allison, their drummer, bought a Triumph Trophy. Holly was transfixed by a black Ariel Cyclone 650cc and purchased the limited edition model – one of only 200 that were ever built. To go with their new wheels, the trio purchased matching Levi’s jackets and peaked caps adorned with wings (pictured) and rode the 350-mile trip home in a thunderstorm.

Fatal plane crash

In the winter of 1958, Holly assembled a new band for his Winter Dance Party Tour, including Tommy Allsup on guitar, drummer Carl Bunch, and fellow West Texan and close friend Waylon Jennings on bass. By February, the band was exhausted from months of touring and sick of the bitter winter weather. Holly decided to charter the band to their next performance in Moorhead, Minnesota.

Also touring with the group were J.P “The Big Bopper” Richardson and Richie Valens. Richardson asked Jennings if he would consider giving up his seat on the plane, as Richardson had been sick with the flu. Jennings agreed, and at the same time, Valens made a similar arrangement with Allsup, leaving Holly on the plane with Richardson and Valens while the other band members rode the tour bus.

The next morning, the news poured in from every outlet: the plane had crashed, killing all three passengers as well as the pilot in a tragic event dubbed “The Day the Music Died.” Jennings lost his closest friend, and for years felt that he was to blame. He gave up playing guitar and performing for two years, eventually leaving Texas for Arizona in hopes that he might find his way again.

After Holly’s death, the Ariel motorcycle stayed with the Holly family until they sold it in 1970. In 1979, Allison, Maudlin, and a third member of the Crickets, Sonny Curtis, approached the bike’s owner and put in an offer to buy it as a gift for Jennings’ birthday. Finally, Holly’s beloved Ariel found its way to Jennings on his forty-second birthday. 

Buddy Holly's Ariel 

The bike is a 1958 Ariel Cyclone with a high compression 650 cc headmaster engine bears engine number CNLF 4510, chassis number CAPR 1069.

The entire collection can be previewed at the Musical Instrument Museum (MIM) in Phoenix, Arizona on October 3-4 from 10:00am to 9:00pm. The live auction will take place in two sessions on Sunday, October 5, beginning at 1:00pm. Absentee bidding via telephone and internet can be arranged. For additional information, visit Guernsey's or contact them at 212-794-2280 or