Waylon Jennings and wife Jessi Colter: The Outlaw Couple

Waylon Jennings and wife Jessi Colter’s love story is considered one of the greatest love stories in country music, and it’s not surprising why. Jennings experienced three failed marriages before he finally found the one, and as they say, love is indeed sweeter the fourth time around. Jessi was by his side through all his glorious highs and through all his lowest lows. And even with all the challenges that their marriage faced, Jessi remained by his side until his death in 2002. 

So, let’s revisit the 33 years of marriage of the outlaw movement’s “it” couple. And discover how it really feels to be truly in love. 

First Chapter: Fourth Time’s The Charm

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Waylon Jennings’ early life was something straight out of the familiar tunes of country music – dropping out of school, doing drugs and getting into trouble, and being not so lucky in love. But over time and through experience, he was able to weather all the storms and also find a long-lasting love with Jessi Colter. 

Jennings first married in 1956 at the age of 18 to his first love Maxine Lawrence. They had four kids – Terry Vance, Julie Rae, Buddy Dean, and Deana – together but their relationship ended later on. Then in December 1962, he married his second wife, Lynne Jones, with whom he had an adopted child named Tomi Lyne. But the second time still did not work, and Jennings, being known as one not to stay single for a long time, married Barbara Rood the same year he divorced Jones. Unfortunately, things didn’t work out for them as well, and later on, they divorced.

But as they say, the fourth time’s the charm. Just when Jennings was about to give up finding love, he found it. And this time around, it was a love for the long haul. 

In an interview, Jennings shared that when he met Jessi, he was at his lowest point. He weighed 138 pounds, and he was on the verge of self-destruction. He wallowed in self-pity and stayed depressed and even stoned all the time. But if there was one thing about true love is that it can still be found even when you’re a mess. And that was what happened, and for Jennings, Jessi was the best thing that ever happened to him. 

Second Chapter: The Glorious Highs 

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Jennings helped her secure a deal with RCA, which was a turning point in Jessi’s life. At that point, she finally changed her stage name to Jessi Colter in honor of her great-grandfather Jesse Colter. After that, Waylon Jennings and Jessi Colter started collaborating, and Jessi also released her debut album “A Country Star Is Born,” co-produced by Jennings. 

In 1970, the two scored a Grammy nomination for “Suspicious Minds.” Then in 1975, she moved to Capitol Records and earned her first chart-topping hit with “I’m Not Lisa” as a solo artist. After that, their respective careers enjoyed back-to-back successes, including their compilation album in 1976 titled “Wanted! The Outlaws” with Willie Nelson and Tompall Glaser selling over a million copies. 

They were quickly dubbed as the outlaw’s movement “it” couple and became very important figures in country music as well. The two wed in 1969 in a church in Phoenix, Arizona, with Jessi’s mother serving as the minister. 

On May 19, 1979, they welcomed their first and only son Waylon Albright “Shooter” Jennings, who later on followed their footsteps.

Who is Waylon Jennings’ wife, Jessi Colter?

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Born as Mirriam Johnson, Waylon Jennings’ spouse Jessi Colter was born on May 25, 1943 in Phoenix, Arizona, to a Pentecostal preacher mom and a race-car driver dad. And she was one of the few female country music artists to emerge during the outlaw movement of the ‘70s.

At the early age of 11, she was already their church’s pianist. She attended Mesa High School, and after graduating in 1961, she already started singing in local clubs in her hometown. Shortly after, she met and married rockabilly guitar legend Duane Eddy, and they had a daughter named Jennifer. 

She pursued a songwriting career at the time and released two singles, including “Lonesome Road,” which only received scattered airplay. Nevertheless, she still toured with then-husband Eddy, but they ended up divorcing in 1968. 

A year later, she met Waylon Jennings, who became her husband and also her partner in the industry. Together, they enjoyed success after success both in their relationship and as country music artists. 

Third Chapter: The Storms And The Lowest Lows

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But just like any relationship, it wasn’t always smooth sailing for the couple as well. During the early 1980s, the couple almost divorced due to Jennings’ severe cocaine and alcohol addiction. On top of that, despite being one of the most successful country musicians of his time, he was almost broke. He would even disappear for days at that point in his life.

Thanks to his son, Shooter, Jennings finally had the strength and inspiration to end all his addiction for good. 

Fourth Chapter: Till Death Do Us Part

Waylon Jennings and wife Jessi Colter loved fiercely until Jennings drew his last breath due to diabetic complications on February 13, 2002. They withstood everything and had an amazing run of 33 years. According to Colter, she just loved him. She was the fourth wife, and he had already tried thrice, and no one really understood him. He made her laugh, feel loved, and most of all, inspired her.