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Waylon Jennings Had Several Failed Marriages before Meeting Soulmate Who Sacrificed Her Needs for Him

Esther NJeri
Jun 20, 2022
04:00 P.M.
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When singer Waylon Jennings met the love of his life, Jessi Colter, he had come from three failed marriages. However, his union with Colter became his saving grace and helped him overcome his demons. They stayed married until he died in 2002.


There is someone for everyone, and Colter was the one for Jennings. According to the "Storms Never Last" singer, the three women her husband had been married to did not understand him.

On the other hand, Colter, a singer recognized for her hits "I'm Not Lisa" and "What's Happened to Blue Eyes," among many others, was also married before meeting Jennings.

American guitarist Duane Eddy sitting in the back seats of a car with his wife Jessi Colter, UK, 11th November 1963 | Source: Getty Images


Her first husband was the rockabilly legend, Duane Eddy. He produced a single for her in 1961, supported and helped Colter with her singing dreams, and her star began shining bright. After marrying, the couple welcomed a daughter, Jennifer.

But in a while, Colter started seeing Jennings despite being married. While Jennings did not want any part of it, Colter could not be dissuaded, and Eddy began getting jealous. Eventually, the two separated in 1968 and divorced later that year.

Jessi Colter photographed on The Outlaw Country Cruise from Tampa to Cozumel on March 1, 2017. | Source: Getty Images


Colter and Jennings met while still married to their respective spouses. They did a song together, and in retrospect, Colter wonders what she was thinking while making the music with Jennings.

The song had been about a marriage gone wrong, living with pain, and dealing with the results of a ruined relationship.

While she was not consciously telling the story of her marriage, she realizes now that she may have bared her struggles to Jennings, albeit unknowingly, as most writers dip into the dark recesses of their minds for the material.

Jessie Colter performing on the ABC tv series 'The Jim Stafford Show' circa 1975 | Source: Getty Images


She was sad but wanted to paint the picture that everything was alright. That she was making do as a wife, a mother, and a songwriter.

As her marriage progressed, she realized she no longer wanted to stay in a union characterized by increased anger and the absence of romance. She suffered silently and wanted an end to it.

She cut the cord and got divorced, despite thinking of divorce as an emotionally ugly business and an admission that no one wanted to make it work.



Colter would later learn that Jennings was also unhappy in his marriage. By the time Colter and Jennings were getting together, Jennings had five children, four from his marriage to Maxine Caroll Lawrence and one adopted during his five-year marriage to Lynne Jones.

According to one of Jennings' sons, Terry, his children knew of their dad's womanizing ways and were aware of his many girlfriends before settling down with Colter. However, like their dad, Terry also picked Colter over the rest of their dad's "wives-in-waiting."

Jessi Colter and Waylon Jennings perform onstage at the Poplar Creek Music Theater in Hoffman Estates, Illinois, on September 3, 1984. | Source: Getty Images


While Colter and Jennings would later become one of the most iconic couples in country music's outlaw movement, their marriage wasn't always a walk in the park. According to Terry, the marriage only worked because Colter put up with a lot of Jennings's behavior. She would tell CMT, as The Boot reports:

"I just loved him ... I loved him! He really entertained me. He made me laugh. He made me feel loved. He inspired me."

Nevertheless, their one goal was to keep the family united. During their 25th anniversary, Jennings shared with Terry that he wanted to plan an intimate celebration that would include him and Colter renewing their vows. He also wanted all his children and grandchildren present.


Waylon would also disclose that before he and Colter married, Colter wrote Jennings a letter saying that he was a wild stallion and needed someone that would let him run free. Years later, Jennings was defending himself to Terry's wife Debra, telling her:

"You don't understand — Jessi begged me to marry her."

Colter denied Jennings' claims, and when he brought out the letter to make his point, she downplayed it. Terry shared that he had nothing but good things to say about Colter.

Jessi Colter and Waylon Jennings in January 1988 | Source: Getty Images


Fortunately, once Jennings sobered up in the 80s, he became a different person altogether, and Colter reaped the fruits of her patience with him.

However, to reach that point took a lot of work, and Colter would reveal that she had had to sacrifice what she needed or wanted to follow Jennings' strong mind.

Even though Jennings always supported her in pursuing her career, even insisting they release a duet album, "Leather and Lace," Colter felt the need to sacrifice her career for her children.

Jesse Colter performs during the Nikki Mitchell Foundation: An Intimate Celebration at Country Music Hall of Fame and Museum on April 1, 2015 in Nashville, Tennessee. | Source: Getty Images


She wanted to spend time with her younger kids. Jennifer was a teenager, and the child she shared with Jennings, Shooter, was only a toddler. She would say:

"They needed my undivided attention, and I was grateful to grant them just that."


Waylon Jennings performs with 'Willie Nelson' at the Spartan Stadium in San Jose, California on July 26, 1982 | Source: Getty Images


Their marriage experienced ups and downs like any other, and they even came close to divorcing in the 80s due to Jennings' severe drug and alcohol addiction. However, they chose to stick to each other until Jennings breathed his last in 2002.

Jennings was more than just a singer. He was a music legend recognized for pioneering the outlaw movement in country music and was inducted into the Country Music Hall of Fame in October 2001.

Besides his career, he also left behind a legacy. He had seven children, five of who were biologically his, one adopted, and one who was from his fourth wife's previous marriage.

Waylon Jennings on January 1 1980 in the United Kingdom | Source: Getty Images


Terry Vance Jennings was the singer's oldest child from his first marriage to Maxine Caroll Lawrence. He eventually became a production manager and co-authored a book with his father "Waylon: Tales of My Outlaw Dad." Sadly, he passed away in 2019, aged 62.

Buddy Dean Jennings was the singer's second child, a skilled guitarist who worked as a bass player in Buddy Holly's band. He has been a regular at his brother Shooter's concerts and tribute events for his father over the years.

Julie Rae Jennings was Terry and Buddy's sister, who sadly passed away in 2014 after battling cancer. Deana Jennings, the youngest of the singer's children from his first marriage, passed away in 2015.


Shooter Jennings and Jessi Colter attends the Waylon Jennings Tribute at SiriusXm Studio on December 6, 2011 in Nashville, Tennessee | Source: Getty Images

Tomi Lynne is Jennings' adopted daughter during his marriage to Lynne Jones, while Jennifer is the daughter of the singer's fourth wife, Colter, from her previous marriage.

The youngest of the brood, Waylon "Shooter" Albright, was the singer's only child with his fourth wife, Colter. He became a country singer like his father and released nine studio albums. He has two children with actress Drea de Matteo but married Misty Brooke in 2013.