There’s nothing quite like the steady love of a good woman to help an outlaw face his demons.
For Waylon Jennings, that woman was Jessi Colter.
And according to Kris Kristofferson, theirs was nothing less than a “beautiful love affair.”
From Phoenix to Outlaw Royalty
A native of Phoenix, Arizona, Jessi Colter was first married to rockabilly guitar legend Duane Eddy. After that marriage ended, fate stepped in.
She met Waylon Jennings — a hard-living, larger-than-life country renegade with a restless spirit and a complicated past. They married on October 26, 1969, in the same Phoenix church where Jessi’s mother served as minister — a poetic beginning for a union that would help define the outlaw era.
Together, they became central figures in country music’s rebellious 1970s movement. In 1976, Wanted! The Outlaws, featuring Waylon, Jessi, Willie Nelson and Tompall Glaser, became the first country album in Nashville history to go platinum.
But their most meaningful collaboration wasn’t on vinyl.
It was their son, Shooter Jennings, born May 19, 1979 — a living continuation of outlaw blood and music.
Love Through the Storm
Waylon had been married three times before Jessi. By the time they found each other, he had endured failed relationships, addiction struggles, and the weight of fame.
Jessi understood him in a way others hadn’t.
“I was his fourth wife, and he had tried with these different women that didn’t really understand him,” she once said. “I just loved him… I loved him! He really entertained me. He made me laugh. He made me feel loved. He inspired me.”
Through years of cocaine addiction and self-destruction, she stayed. She prayed. She waited. And eventually, Waylon made the decision to get sober — a turning point that allowed him to live the remainder of his life with clarity and devotion.
He passed away on February 13, 2002.
A Legacy of Love
“He is missed,” Jessi has said. “There will never be another one like him. He gave me a great life and so many people so many hours of happiness. He played for the people. I loved him dearly.”
Their story wasn’t perfect. It wasn’t polished.
It was real.
An outlaw and a lady.
A storm and an anchor.
A love that helped tame the wildest of hearts — and left behind a legacy that still echoes through country music today.