The song still echoes through bars full of good ol’ boys drinking whiskey and rye. Yet, Don McClean’s “American Pie” only tells the story of the day the music died. February 3rd, 1959, was also the day that Waylon Jennings cheated death. Waylon picked up his first guitar at age 8 but it wasn’t until after his 21st birthday that he caught his big break. He was working as a DJ in Texas when Buddy Holly invited him to recording sessions and later to join the band.
The Winter Dance Party Tour began on January 23rd in Milwaukee, and the busses that the band had rented broke down by the end of the week. Even though they had rented another bus for transportation, Buddy decided to charter a plane for the band to fly to Fargo. Jennings gave his seat to J.P. Richardson who had the flu and didn’t want to take a freezing cold bus. That plane fell into a cornfield in Mason City, Iowa sometime around 1:00 am. Waking the world up with the headline “Buddy Holly and band dead in plane crash”. Jennings, first called his family, then dialed in KLLL, the radio station he had worked for to let everyone know he was alive. During a CMT interview, Jennings spoke about Buddy joking about another bus breaking down, to which he replied with “I hope your ol’ plane crashes” Although Waylon felt like he had cursed the plane, he was able to find peace and continued to make music in their honor. No more than a month later after previously recording with Buddy, Waylon released “Jole Blon” however given that everyone was still in shock, the song didn’t break the charts. Waylon moved to Nashville, jumped from one record label to another and found a nice apartment to rent with his friend Johnny Cash. They both toured nearly all year, spending almost 300 days on the road, leading to debt piling up, which certainly didn’t help his struggles with addiction.
In 1972, Jennings released Ladies Love Outlaws, a comeback single that headlines the album became an instant hit, yet he still battled with limited artistic freedom in Nashville. “They wouldn’t let you do anything, you had to dress a certain way, you had to do everything a certain way.” Months later, nearing the end of his recording contract, Waylon was diagnosed and hospitalized with hepatitis, leading him to contemplate retirement. Later in 1973 Waylon starting writing songs again. Jennings then released Honkey Tonk Heroes and Lonesome On’ry and Mean. These albums were the first view we had at his true artistic genius and brought his most successful years. By 1976, Waylon and Willie Nelson had finally teamed up and recorded Wanted! The Outlaws. They made such a great duo that later morphed into, The Highwaymen, one of the greatest supergroups there has ever been. Waylon Jennings, Willie Nelson, Kris Kristofferson, and Johnny Cash. WWII was their golden album that released in 1982 and is certainly a testament to all four of their very successful careers.
As for Waylon, six packs of cigarettes a day finally caught up with him. He was sick and stopped touring, then his diabetes worsened and he began living his final months in a hospital in Phoenix. February 13th 2002 Waylon left this earth, but his songs will live forever. While there are stories of every size, shape and color, the one rarely told is how Waylon Jennings cheated death and survived the day the music died.