Each week, I host a “crowdsourced playlist.” I give the theme (and a few examples) and the crowd throws in their suggestions. Check out the progress on this week’s playlist below, or head over to Facebook to follow me and contribute.
In 1959, a 21-year-old Waylon Jennings was booked for a late-night flight from Clear Lake, IA to Fargo, ND with other members of the band he was playing with at the time.
J.P. Richardson—a.k.a., The Big Bopper—was also traveling making the trip from Clear Lake to Fargo, but with no open seats on the plane, he was to take a bus. Today that trip takes about 5.5 hours, but none of the sections of I-94 or I-35 connecting the two cities had been built in 1959 and the bus trip would likely have taken much longer. Jennings took pity on Richardson, who was sick with a cold, and gave up his seat on the plane, joking “I hope your ol’ plane crashes.”
The plane crashed, killing Richardson, as well as Buddy Holly and Ritchie Valens.
I was a highwayman. Along the coach roads I did ride, With sword and pistol by my side. Many a young maid lost her baubles to my trade. Many a soldier shed his lifeblood on my blade. -The Highwaymen
Several years later, Jennings shared an apartment with Johnny Cash, the two roommates having a heavy addiction to amphetamines in common. Both musicians’ careers were doing well around this time, but Jennings was becoming frustrated with the artistic control exerted by the Nashville producers.
In 1972, Jennings released the album ‘Ladies Love Outlaws.’ Subsequently, he renegotiated his recording contract to permit greater creative freedom and released ‘Lonesome, On’ry and Mean,’ the “quintessential” outlaw record (AllMusic.com).
It’s fun to wonder what The Big Bopper and Buddy Holly might have gone on to do had they lived, but it’s amazing to think that if Jennings had boarded that plane, we might never have had Outlaw Country or many of the other outlaw and gangster songs that followed. Others, like Cash, had been “bad boys,” but none had made the “outlaw” such a part of their performative identity.