Roughly 17 years after his first marriage and shortly before his career was about to skyrocket, Waylon met and married fellow country music artist Jessi Colter. It would be Waylon Jennings’ fourth marriage. In a 1988 interview with Spin, Jennings candidly discussed the toll his wild living and addiction had taken on not just himself but those who loved him. He also attributed his sobriety to Colter, saying, “that was one of the reasons why I was able to pull out of [addiction] because I saw it on my wife Jessi’s face.” Hank Williams Jr. even playful referenced the change in his song “All My Rowdy Friends Have Settled Down,” singing, “And Waylon’s staying home and loving Jessi more these days.” 

While Colter and Jennings went on to have a son (the musician known professionally as Shooter Jennings), it wasn’t always marital bliss for the couple. Alluding to trouble with fidelity on the road, Jennings remarked in that same Spin interview that the pair had a very honest relationship. Even though Colter “had a lot of things to understand,” he went on to speculate that “she is the only person in the world who could have been married to me and stayed with me.” Indeed, the two remained married until Jennings’ death in 2002.