By the late 1950s, Waylon Jennings was among a group of west Texas musicians looking to hit the jackpot at the intersection of country and the burgeoning rock 'n' roll movement.
Buddy Holly represented the mold to follow – a boy from Lubbock who'd blossomed in the wake of Elvis Presley's debut and captured America's attention through now-classic tracks like "That'll Be the Day" and "Peggy Sue."
Through his DJ job at Lubbock's KLLL, Jennings grew close to Holly and found an early champion of his abilities, with the rocker producing and contributing guitar work to Jennings' first recordings.
Still, as he recalled in his 1996 autobiography, Jennings was surprised when Holly burst into the KLLL studios one day, thrust an electric bass guitar at him and said, "You have two weeks to learn to play that thing."
Buddy Holly and the Crickets had been booked as headliners for the early 1959 Winter Dance Party Tour, but at the time the Crickets were nonexistent, and Holly needed backing musicians. He hired Tommy Allsup on guitar and Carl "Goose" Bunch for drums, while Jennings, a guitarist, listened to Holly's catalog nonstop as a crash course for his first major gig.
The musicians endured terrible conditions on tour
Set up by Irving Feld's General Artists Corporation, the Winter Dance Party Tour was to feature J.P. "The Big Bopper" Richardson, 17-year-old Ritchie Valens, doo-woppers Dion and the Belmonts and a lesser-known New York City singer, Frankie Sardo, to accompany Holly and his "Crickets" as they traversed the upper Midwest from late January to mid-February.
While the tour was welcomed by teenyboppers through the bleak winter months, it was hardly a party for the musicians who spent most of their days and nights crammed into a frigid bus, motoring on to the next gig with no time off.
Underscoring the challenges of their task, the tour bus broke down while attempting to make the 300-plus-mile overnight trip to Green Bay, Wisconsin, following their January 31, 1959 show in Duluth, Minnesota. After burning newspapers to keep warm in the bus, the musicians managed to flag down cars to take them to safety in a nearby town, though Bunch wound up in a hospital with frostbitten feet.
Jennings gave up his plane seat to a flu-stricken Big Bopper
Fed up with the conditions, Holly decided to charter a plane to cover another massive gap between gigs, this one spanning the 400 miles between their February 2 show in Clear Lake, Iowa, and the next day's performance in Moorhead, Minnesota.
Jennings and Allsup agreed to fork over $36 apiece for the chance to arrive early, stretch out in a hotel bed and do some much-needed laundry. However, between sets of their Clear Lake show, Richardson persuaded Jennings to give him his spot on the plane. At more than 250 pounds, the aptly named Big Bopper could barely squeeze into a bus seat, and he was desperate for some sleep to fight off the flu.
Meanwhile, Valens leaned on Allsup to do the same, though he acquired his coveted seat only after getting the stubborn guitarist to agree to a coin toss.
The last time Jennings remembered talking to Holly, the frontman was chiding him for chickening out of the plane ride. "I hope your damn bus freezes up again," Holly said, smiling.
Jennings replied with the words that haunted him for years: "Well, I hope your ol' plane crashes."
Their flight took off from nearby Mason City airport at approximately 1 a.m. on February 3 but, due to the combination of snowy conditions and the inexperience of pilot Roger Petersen, the aircraft plummeted into a field a few miles away. Holly, Richardson, Valens and Petersen were immediately killed, a moment immortalized in Don McLean's 1971 hit, "American Pie," as "the day the music died."
READ MORE: The Day the Music Died: Rock’s Great Tragedy
Jennings always remembered Holly's advice
In shock following the death of his good friend and mentor, especially considering his ominous parting words, Jennings barely got through the remaining two weeks of the tour. Rejecting an offer to join the re-formed Crickets, he headed back to Texas with "no intention of ever playing another note."
Fortunately, Jennings overcame his grief and guilt and returned to his calling, eventually becoming a symbol of the outlaw country genre of the 1970s through career-defining hits like "This Time" and "I'm a Rambling Man" and a stubborn insistence on doing things his way.
He never forgot the influence of Holly, who took the then-unknown musician under his wing and imparted some important lessons during their brief time together. "Don't ever let people tell you you can't do something," he recalled, "and never put limits on yourself."
"Years later, I'd be in the studio, and the track would really get in the pocket and feel good, and I'd hear those Nashville producers saying scornfully, 'Man, that sounds like a pop hit,'" continued Jennings. "And I'd remember Buddy talking to me, telling me they thought he was crazy, as that freezing bus moved down the highway from Green Bay, Wisconsin, to Clear Lake, Iowa."