On This Day in 1969, One of Outlaw Country’s Founding Fathers Tied the Knot for Good: “Ever Since I’d Gone Out on the Road With Waylon, I’d Been Packing a Wedding Dress”

After a string of short and unsuccessful marriages, Waylon Jennings finally settled down with fellow country singer Jessi Colter on October 26, 1969, less than one year after their relationship turned romantic. In her memoir, An Outlaw and a Lady, Colter admitted that Jennings’ proposal didn’t surprise her. “I saw it coming months before,” she wrote. “In fact, ever since I’d gone out on the road with Waylon, I’d been packing a wedding dress. Nothing fancy, mind you, but a suitable outfit.” As it would turn out, she was right to do so.

Videos by American Songwriter

Although she didn’t lay out the specifics of how he asked her to marry him, Colter said she stayed silent for what must have felt like an eternity to Jennings. Instead of responding with a yes or no, she asked him, “Just like that?” He replied, “Just like that.” Colter admitted she had some doubts about marrying him, and he said that was one of the reasons he loved her so much—she was honest. And it’s not like Colter had no reason to worry. Jennings was infamously difficult to be in a relationship with, whether because of drugs, infidelity, or both.

Moreover, they were both professional musicians. Would marrying Jennings mean giving up her own career? If they didn’t work out, would that affect their artistic reputation? While Colter let these questions rattle around in her head, Jennings said, “If I know you—and I think I do—you won’t let those doubts stop you. So, just say yes, and let’s get on with it.” So they did.

Waylon Jennings and Jessi Colter Married in Las Vegas in 1969

As one might expect from a proposal that included the words, “let’s get on with it,” Waylon Jennings and Jessi Colter didn’t waste their time with a lengthy engagement. The couple went to Las Vegas, Nevada, for a quick elopement at City Hall. Colter recalled “nervously laughing” throughout the day. “I laughed when we got to the Las Vegas City Hall; I laughed when Waylon’s best man turned out to be his bass player who hit the same wrong notes every night and whose chief job was to carry the money briefcase; I laughed when the justice of the peace, whose deadly monotone that gave the impression that this was his hundredth wedding of the day, called me Mary instead of Mirriam.”

Sometimes, Colter laughed to cover up feelings of regret or hurt. Looking out at her witnesses and realizing she didn’t have any of her family or friends there, she laughed again. “I was nervous and scared and convinced that this was either the best day of my life or the worst. I laughed because I didn’t know what else to do.”

The newlyweds had a champagne dinner at the Golden Nugget, where Colter continued to laugh. Jennings pointed out the fact that she had been nervously giggling all day, to which she replied, “If I don’t laugh, I’ll cry. He asked, “Cries of regret or cries of both?” Colter said both.

“For crying out loud, girl, just admit it,” Jennings said. “There ain’t no one in this whole dang world you’d rather marry than me.”

Jennings was right, too. The country singers would remain married until Jennings’ death in 2002. They had one child together, Waylon Albright “Shooter” Jennings. Colter remarried two decades after Jennings’ death to Arlin Brower in June 2023.

Photo by Paul Natkin/Getty Images