Remember When: Willie Nelson and Jennings Broke Down on the Side of the Road and No One Stopped to Help Them

By the mid-1970s, Waylon Jennings and Willie Nelson were the outlaws leading the way in the country. After first meeting in Phoenix, Arizona in 1965—when Nelson warned Jennings not to move to Nashville—the two became friends and continued collaborating throughout the ’70s and Jennings’ lifetime.

Before both appeared together on the 1976 compilation, Wanted! The Outlaws, along with Jennings’ wife Jessi Colter and Tompall Glaser, Nelson co-wrote a collection of songs for his fellow outlaw, including his 1971 hit “Good Hearted Woman” and “Pretend I Never Happened” in 1972. In 1977, Jennings’ album Ol’ Waylon also featured Nelson on the final verse of the opening track “Luckenbach, Texas (Back to the Basics of Love).”

A year later, the pair released their debut collaborative album, Waylon & Willie, featuring their country hit “Mammas, Don’t Let Your Babies Grow Up To Be Cowboys,” and went on to release more together, including WWII in 1982, and Take it to the Limit from 1983, and their 1991 release Clean Shirt.

Lifelong friends, the two had their ups and downs, including an ill-fated airport pickup that once left them stranded on the side of the road in Texas.

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A Mercedes Benz

Nelson insisted on picking up Jennings and his wife Jessie Colter at the airport one day in the mid-1970s. The couple were going to stay with Nelson and his then-wife Connie Koepke, at their house in Dripping Springs, Texas. Nelson was so excited to pick them up at the airport in his new Mercedes that he forgot to fill the tank with gas.

“Willie picked up me and Jessi at the airport in his new Mercedes,” recalled Jennings in a 1988 interview. “This must be 12 or 15 years ago. We were goin’ out to his house, which is out there close to Dripping Springs, and Willie runs out of gas. That’s just no problem, I mean, we’re in Texas, everybody knows us in Texas. Well, we spent an hour out there, and the people would drive by and wave at us, you know, but nobody would stop, I just couldn’t figure that out.”

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A Lone Star Beer truck, which sponsored most of Willie’s concerts, even drove by the two at the side of the road. “The driver hollered, ‘Hey Willie, Waylon, what y’all doin’? and kept going,” added Jennings. “Well, I said, ‘Wait a minute now, Willie, I’m gettin’ tired of this. Me and you might better get in the car and we’ll set Jessi out here and get us a ride.’”

Jennings continued, “We might still be there if Connie, Willie’s wife, hadn’t happened to come by. I ain’t kiddin’. We was there over an hour and nobody would stop. They like us. They like our singin’, but they don’t want us ridin’ in their cars with em’ now. They ain’t gonna give no hillbillies lookin’ like me and him a ride.”

Photo: Willie Nelson and Waylon Jennings perform on stage together, New York, April 1978. (Michael Putland/Getty Images)