Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Waylon Jennings and wife Jessi Colter: The Outlaw Couple

Waylon Jennings and Wife Jessi Colter Love Story
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

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

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 

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?

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

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. 

Latest Stories

Don Williams and Emmylou Harris Deliver a Classic Duet With "If I Needed You"

Don Williams and Emmylou Harris Deliver a Classic Duet With “If I Needed You”

When Don Williams and Emmylou Harris came together for their duet of “If I Needed You,” they gave life to one of country music’s most cherished ballads. Originally written and ...

Randy Travis and Josh Turner Deliver a Heavenly Performance of "Three Wooden Crosses"

Randy Travis and Josh Turner Deliver a Heavenly Performance of “Three Wooden Crosses”

When Randy Travis and Josh Turner joined forces for a 2006 episode of CMT Cross Country, it was a meeting of country music generations that fans won’t soon forget among ...

Vince Gill and Patty Loveless Honor a Classic With "After the Fire Is Gone"

Vince Gill and Patty Loveless Honor a Classic With “After the Fire Is Gone”

In 2015, Vince Gill and Patty Loveless graced the Austin City Limits Hall of Fame stage with a performance that remains etched in the hearts of country music fans. Their ...

George Strait and Grandson Harvey's Emotional "God and Country Music" Performance

George Strait and Grandson Harvey’s Emotional “God and Country Music” Performance

In 2019, George Strait reminded fans why he’s called the King of Country when he released “God and Country Music” as part of his album Honky Tonk Time Machine. The ...

Kelly Clarkson's "Here's A Quarter" Cover Brings New Life to a Classic

Kelly Clarkson’s “Here’s A Quarter” Cover Brings New Life to a Classic

Kelly Clarkson has a knack for turning iconic songs into showstoppers, and her take on Travis Tritt’s fiery anthem, “Here’s a Quarter (Call Someone Who Cares),” is no exception. During ...

Kelly Clarkson's Stunning Cover of “Smoky Mountain Rain” Showcases Her Country Roots

Kelly Clarkson’s Stunning Cover of “Smoky Mountain Rain” Showcases Her Country Roots

Kelly Clarkson’s Kellyoke performances have given fans countless memorable moments. Still, her heartfelt rendition of Ronnie Milsap’s “Smoky Mountain Rain,” aired on The Kelly Clarkson Show on June 1, 2022, ...

Alan Jackson and Hank Jr. Bring "The Blues Man" to Life With Unforgettable Duet

Alan Jackson and Hank Jr. Bring “The Blues Man” to Life With Unforgettable Duet

There are moments in country music that feel like they were destined to happen—moments when two titans of the genre come together to remind the world why country music remains ...

This Teen's Take on 'Folsom Prison Blues' Feels Like a Johnny Cash Revival

This Teen’s Take on ‘Folsom Prison Blues’ Feels Like a Johnny Cash Revival

There’s something electrifying about a young performer bringing a legend’s music to life. At just 14 years old, Haavard Nilsen didn’t just perform Johnny Cash’s classic “Folsom Prison Blues”—he embodied ...

Lorrie Morgan's Dramatic Take on the Classic "A Picture of Me (Without You)"

Lorrie Morgan’s Dramatic Take on the Classic “A Picture of Me (Without You)”

When it comes to heartbreak anthems, few songs hit as hard as “A Picture of Me (Without You).” Originally recorded by George Jones in 1972, the song is a country ...

Four-Year-Old Braydon's Precious Cover of "As Soon as I Hang Up the Phone" Will Melt Your Heart

Four-Year-Old Braydon’s Precious Cover of “As Soon as I Hang Up the Phone” Will Melt Your Heart

In country music, legends like Loretta Lynn and Conway Twitty have given us timeless classics that continue to resonate across generations. But in 2014, one pint-sized performer brought fresh life ...