Willie Nelson and Waylon Jennings ‘Disagreed on Almost Everything’ but Stayed ‘Great Friends All the Way’

Legendary country music stars, singer/songwriter, Willie Nelson, and the late, great Waylon Jennings, disagreed on a lot of things. But they didn’t let that get in the way of their music-making friendship.

So, how did the two become friends with so many things to disagree about? And which other icons did they eventually rope into their “Outlaw” band?

Willie Nelson and Waylon Jennings on stage, both wearing hats and guitars c. 1985
Willie Nelson and Waylon Jennings | Paul Natkin/Getty Images

Willie Nelson met Waylon Jennings in an all-night restaurant

As Nelson wrote in his memoir, Roll Me Up and Smoke Me When I Die, he met Jennings in an all-night restaurant in Phoenix, Arizona. He recalled he saw him perform one night and stuck around to talk to him. Neither had experienced a lot of luck in their music careers yet, though Jennings played bass for Buddy Holly’s band, the Crickets, and Nelson wrote Patsy Cline’s hit, “Crazy.”

“We hit it off pretty good right from the start,” Nelson noted. And that was because they shared some things in common, like their home state of Texas. They were also both referred to as “Outlaws” of country for not conforming to certain standards.

So, Jennings asked Nelson for advice on whether he should go to Nashville, which Nelson advised him against. He said he thought he could make more if he just stayed where he was.

“I thought he had a better gig than I did,” Nelson confessed. “Fortunately, he didn’t listen to me.”

According to the “Pretty Paper” singer, he and Jennings “stayed great friends all the way” even though they “disagreed on almost everything and argued like old married people.”

Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson formed an ‘Outlaw’ supergroup called The Highwaymen

After trying his hand at the Nashville music scene in the early ’60s, Nelson returned to Texas to regroup and redirect. After that, he started noticing changes in his crowds. He was picking up “hippies” in his audience and they were becoming loyal fans along with the usual cowboys.

Around the same time, Jennings was having a hard time making the music he wanted the way he wanted in Nashville. So, Nelson told him to come down to Texas and see what he’d been seeing. Jennings made the trip and the two began collaborating.

Eventually, they would both fight to break free from traditional sounds and spearhead what became known as the “Outlaw” movement (per CMT.) And they would ultimately pick up country legend, Johnny Cash, and Kris Kristofferson to form a supergroup known as The Highwaymen.

Nelson recalled in his memoir the tours were “the most fun [he] ever had before or since.”

“Kris and Waylon would argue about politics; John and I would laugh a lot,” he wrote. “Later on they would call me just to hear a good joke.”

Waylon Jennings died on Feb. 13, 2002 and Willie Nelson misses him ‘dearly’

On Feb. 13, 2002, Jennings died of diabetes-related illness at the age of 64.

In Roll Me Up and Smoke Me When I Die, Nelson wrote about his love for both Jennings and Cash, who died on Sept. 12, 2003. “They are dearly missed to this day,” he shared before noting he and his last surviving bandmate, Kristofferson, had recently “burned one down and solved all the world’s problems.”

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