The first major step in Waylon Jennings' journey to the Country Music Hall of Fame began as a touring musician for rock & roll legend and Lubbock, Texas native Buddy Holly--A partnership that put Jennings in Holly's life right before one of the most famous plane crashes in American history.
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Holly saw Jennings, a radio DJ since his pre-teen years, as a promising talent and a worthy understudy. The first fruits of the two Texas natives' late '50s partnership came when Jennings recorded the songs "Jole Blon" and "When Sin Stops (Love Begins)" with Holly and guitarist Tommy Allsup.
Next, Jennings went on the road as part of Holly's post-The Crickets backing band for the Winter Dance Party Tour along with co-headliners Ritchie Valens and The Big Bopper (JP Richardson). Winter tour stops in the Midwest were too far apart for unheated tour buses: a condition in which drummer Carl Bunch got hospitalized for frostbite on his toes. To make traveling simpler, Holly chartered a four-seat Beechcraft Bonanza airplane in Mason City, Iowa.
Read More: Waylon Jennings and Jessi Colter: A Classic Country Love Story
The flight from Mason City in between the performers' show at the Surf Ballroom in Clear Lake, Iowa and a scheduled appearance in Moorhead, Minn. became the stuff of legend. Holly bandmate Allsup allegedly lost a seat in a coin toss to Valens, and Jennings offered his spot to an ailing Richardson.
After travel arrangements got sorted out, Holly is said to have spoken chilling last words to Jennings. Holly jokingly told Jennings, "Well, I hope your ol' bus freezes up!" Jennings jokingly replied, "Well, I hope your ol' plane crashes!" This exchange haunted Jennings for years to come after the plane carrying Holly and his co-headliners crashed and killed all passengers, including pilot Roger Peterson.
Fate spared Jennings from the Feb. 3, 1959 plane crash known as "The Day the Music Died," as commemorated in the Don McLean song "American Pie." A split-second decision spared a country legend whose future work with friend Willie Nelson and bride Jessi Colter proved that country music that doesn't conform to Nashville's expectations can sustain a superstar career.
Jennings never forgot Holly's generosity, as represented by some of his great covers over time of Holly originals.
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