Waylon Jennings wasn't exactly the kind of guy who did things by the book. Whether he was telling Nashville producers to take a hike or narrowly missing the plane crash that took Buddy Holly, the man lived at 100 miles per hour. Naturally, his love life was just as chaotic. If you've ever found yourself wondering who was Waylon Jennings married to, you're looking at a list of four very different women who tried to handle the "Waymore Blues."
Honestly, Waylon’s track record with marriage was a lot like his early music career—a few false starts before finding the rhythm that actually worked. He didn’t just wake up as a legendary outlaw; he spent years making mistakes, both in the studio and at home. By the time he found his soulmate, he'd already been through three divorces and enough drama to fill a dozen double-LP albums.
The early years: Maxine, Lynne, and Barbara
Waylon was barely a legal adult when he first tied the knot. In 1955, an 18-year-old Waylon married Maxine Lawrence. This wasn't some short-lived fling, though. They stayed together for about seven years and had four children: Terry, Julie, Buddy Dean, and Deana. It’s kinda interesting to note that Buddy Dean was actually named after Buddy Holly, Waylon’s mentor who died in that 1959 crash. Life was hard back then. Waylon was a struggling radio DJ and a musician playing bars in Texas and Arizona, and the strain of the road—plus Waylon’s "restless" spirit—eventually blew the marriage apart in 1962.
He didn't stay single for more than a minute. Literally that same year, he married Lynne Jones.
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They adopted a daughter named Tomi Lynne during their five-year marriage, but the cracks started showing pretty fast. Waylon was moving to Nashville around this time, sharing an apartment with Johnny Cash and getting deep into a lifestyle that wasn't exactly conducive to a stable home life. They called it quits in 1967.
Then came the marriage most people forget. Waylon married Barbara Elizabeth Rood in 1967. This one didn't even make it two years. No kids, just another chapter in a book that seemed like it was going to end in tragedy. By the late '60s, Waylon was at his lowest point. He was broke, weighing about 138 pounds, and heavily addicted to amphetamines. He basically felt like he was "wallerin' in self-pity," as he later put it.
The Outlaw Queen: Why Jessi Colter was different
Everything changed in 1969. That’s when Waylon met Mirriam Johnson, who the world now knows as Jessi Colter. She was coming off her own marriage to rockabilly legend Duane Eddy. Waylon and Jessi married on October 26, 1969, in a ceremony performed by Jessi's mother, who was a Pentecostal minister.
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You've gotta realize that Jessi wasn't just a "wife" in the traditional sense. She was a powerhouse musician in her own right. In fact, for a few years in the mid-70s, she was actually more famous than Waylon. Her hit "I'm Not Lisa" was a massive pop and country crossover. While Waylon was fighting RCA Records to let him use his own band, Jessi was already topping charts.
Their marriage became the foundation of the "Outlaw" movement. When they released the Wanted! The Outlaws album in 1976 with Willie Nelson, it became the first country album to sell a million copies. They were the ultimate power couple, but it wasn't all gold records and sunshine. Waylon’s drug habit was brutal. He was spending upwards of $1,500 a day on cocaine at one point. Jessi almost left him several times. She stayed, though, and Waylon often said she was the only person on earth who could have handled him.
The children of the Waylon legacy
Waylon's family tree is pretty sprawling because of those four marriages. If you're trying to keep the kids straight, here's the breakdown:
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- With Maxine Lawrence: Terry Vance (who later wrote a book about his dad), Julie Rae, Buddy Dean, and Deana.
- With Lynne Jones: They adopted Tomi Lynne.
- With Jessi Colter: They had one son, Waylon Albright "Shooter" Jennings, born in 1979.
- Bonus Family: Waylon also raised Jessi’s daughter from her first marriage, Jennifer (Jenni) Eddy, as his own.
It's actually pretty cool to see how that legacy continued. Shooter Jennings ended up playing his father in the movie Walk the Line and has become a massive producer and artist. Even Jenni’s son, known as Struggle Jennings, is a successful musician. The "Outlaw" spirit stayed in the bloodline.
What happened at the end?
Unlike his first three attempts, Waylon’s marriage to Jessi Colter lasted until the day he died. They were married for over 32 years. Waylon finally got clean in 1984, famously quitting cold turkey because he couldn't stand to see the pain on Jessi’s face anymore. He traded the drugs for a more stable life, though his health eventually caught up with him due to years of heavy smoking and diabetes.
When he passed away in his sleep in 2002, Jessi was there. She has spent the years since keeping his legacy alive, releasing her own memoirs like An Outlaw and a Lady and helping produce tribute albums.
To really understand Waylon's story, you have to look at the people he surrounded himself with. To dive deeper into the history of the Outlaw movement or to hear the music that defined these relationships, you should start by listening to the duets between Waylon and Jessi, like their cover of "Suspicious Minds." It captures the tension and the love better than any biography ever could. You can also look up Terry Jennings' memoir for a raw look at what it was like growing up as the son of a legend.
Check out these steps if you want to explore the Jennings family history further:
- Listen to the album Wanted! The Outlaws to hear the musical peak of Waylon and Jessi’s partnership.
- Read Jessi Colter's memoir, An Outlaw and a Lady, for the definitive account of their 30-year marriage.
- Follow Shooter Jennings' current projects to see how the family's musical style has evolved in the 21st century.