Waylon Jennings’ World of Surprises

Musician Jessi Colter, widow of Waylon Jennings, recalls the moments the country legend surprised her most
Waylon Jennings’ World of Surprises

Illustration Jason Raish

For 33 years, i was married to Waylon Jennings. As ornery and challenging as he might have been, I adored him—he was my cowboy. Our life together was nonstop movement. As working musicians, we ran around the world doing our best to entertain audiences from Austin to Auckland. Of the thousands of road stories I cherish, here are three of my favorites:

During a snowy winter in magnificent Montreux, Switzerland, we arrived to tape Johnny Cash’s TV Christmas special. It was the mid ’80s, and for the first time Johnny, Waylon, Willie Nelson and Kris Kristofferson were working together. This was the genesis of the legendary Highwaymen. When the show was over, Waylon suggested I fly off to Paris because he had post-production work to do. I wondered if he had hidden motives. In fact, he did. He had booked the plush Hemingway suite at the Ritz Paris and hired a chauffeured Rolls-Royce to drive me around the City of Light. I was living in a fairy tale.

Driving through dusty West Texas, the territory of Waylon’s childhood, I spotted a 1966 Mack Truck on the side of the road. Maybe because my dad was a racing champion who could build a car from the ground up, I’ve always felt that vehicles carry an aura. This truck spoke to me. It said, “I’m lonely.” “We need to adopt it,” I told Waylon, and we did. Much to my surprise, Waylon tricked it out in black lacquer and christened it Miss Jessi. Friends placed a big golden Mack bulldog on Miss Jessi’s nose. Bless her soul, Miss Jessi became a star. Trucker magazines put her on the cover. And I never felt more comfortable or secure than when I sat in her cabin, either behind the wheel or by my husband’s side. Miss Jessi was never lonely again.

The jet soared through dark storm clouds into brilliant sunlight. It was smooth sailing ahead. It was also my birthday. Waylon and I were flying from Florida to a gig in San Jose, California. “There’s a surprise coming,” Waylon promised. “What is it?” I asked. “All I can tell you,” he said, “is hold on to your seat.” Not knowing what in the world he meant, I closed my eyes and drifted into a deep sleep. Hours later, he startled me awake. “It’s coming, Jessi! It’s almost here!” Then, without warning, the jet took a precipitous dive. I grew alarmed. “Nothing to worry about,” Waylon assured me. “Just look out the window.” There was the most awesome sight: Mt. St. Helens in full eruption. We swooped down to what felt like inches from the swirling smoke and shooting flames. The miracle of nature. The energy of God. The best gift I’ve ever received.

As a traveler through life, Waylon was all about spontaneity. Despite turmoil, his nature gave me delightful surprises and caught me at the right unexpected moments. Those moments made me rich. Waylon’s spirit was both irresistible and invincible. That beautiful spirit is as alive today as it was some 40 years ago when we first met.

Jessi Colter’s autobiography, An Outlaw and a Lady: A Memoir of Music, Life with Waylon, and the Faith that Brought Me Home, is out now.