Waylon Jennings

The Winter Dance Party

The Winter Dance Party was the infamous, ill-fated tour through the mid-west in the dead of winter featuring Buddy Holly, Ritchie Valens, and the Big Bopper (among others). Waylon Jennings was a member of the Buddy Holly band (note Waylon was not a member of the Crickets) during the tour. Before their performance at the Surf Ballroom in Clear Lake, Iowa, Holly chartered a four-seat Beechcraft Bonanza airplane from Dwyer Flying Service in Mason City, Iowa, for himself, Jennings, and Tommy Allsup, to avoid the long bus trip to their next venue in Moorhead, Minnesota. Following the Clear Lake show (which ended around midnight), Allsup lost a coin toss and gave up his seat on the charter plane to Ritchie Valens, while Jennings voluntarily gave up his seat to J. P. Richardson, known as The Big Bopper, who was suffering from the flu and complaining about how cold and uncomfortable the tour bus was for a man of his size.

When Holly learned that his bandmates had given up their seats on the plane and had chosen to take the bus rather than fly, a friendly banter between Holly and Jennings ensued: Holly jokingly told Jennings, “Well, I hope your ol’ bus freezes up!” Jennings jokingly replied, “Well, I hope your ol’ plane crashes!”[32] Less than an hour and a half later, shortly after 1:00 am on February 3, 1959, Holly’s charter plane crashed at full throttle into a cornfield outside Mason City, instantly killing all on board.

Those words, uttered in jest, haunted Jennings for decades to come.