Waylon Jennings and wife Jessi Colter: The Outlaw Couple

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. 

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