They’re two of the most iconic country singers of all time, and they’re synonymous with each others careers… but do you know how they actually met?

Willie Nelson and Waylon Jennings spent decades building careers that were equally as legendary as they were totally fueled by a drive to do things their own way, and put out the music that they believed in.

They fought record labels for creative freedom, never wavered on what they believed in, and became icons for not only putting out great music, but putting up the good fight to be able to do so and blazing the trail for so many who have come up behind them.

Of course, they put out a lot of music together over the years, including country classic like Waylon & Willie in 1978, which featured the hit duet “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” in addition to being part of the first ever Platinum-selling country album, Wanted! The Outlaws in 1976 along with Jessi Colter and Tompall Glaser.

But before they became a duo of sorts, Willie and Waylon were playing in Austin, Texas, pioneering what we now call the outlaw movement, and it’s one of my favorite times in country music history.

Though they didn’t actually meet in their home state of Texas, believe it or not… they met in Arizona.

In the mid-60’s when Waylon was headlining JD’s, “a rowdy dance hall and drinking hole” as Willie puts it, Waylon was a big hit at the night club near Arizona State that college kids loved. Upon their first meeting sometime back in 1965, well before the outlaw movement had even started, Waylon informed Willie he wanted to move to Nashville and asked for the red headed stranger’s advice.

Waylon wanted to leave Arizona because it was “too f***** confining for him” and he was ready for a change, which Willie, never one to stay in one place for too long, fully understood. And Willie, who’d had some previous success in Nashville as a writer but was struggling to find his voice as an artist there, also had some thoughts about it.

He asked Waylon what he wanted to do in Music City, and detailed the fascinating conversation in his 2015 memoir It’s a Long Story: My Life, to which Waylon stated plainly:

“Cut me some hit records, sell me some hit songs. What do you think, hoss?”

Willie seemed a little hesitant in answering further, already picking up the fact that it would probably fall on deaf ears and Waylon was likely going to do what he wanted no matter what:

“I think you’re gonna do what you’re gonna do, Waylon. But if you’re asking my advice…”

And you can probably see where this is going…

Willie told Waylon he should  “stay away from Nashville,” because record execs and people in the industry would try to change pretty much everything about Waylon, his music, and his way of doing things:

“Well, sir, after having been in Nashville for some time, I don’t see it as your town. Nashville will wanna mold you, and you don’t need no molding. Nashville will wanna clean you, and you don’t need no cleaning… you need to stay away from Nashville.”

Amen to that, Willie.

Waylon assured Willie he heard him, though the next thing he knew, Waylon had left Phoenix and moved to Nashville, and just like Willie, was signed by Chet Akins to RCA Records.

Of course, it worked out for both of them in the long run, and the pair completely changed the genre with their authentic music and refusal to follow a formula and conform completely to the Music City industry.

It was a heck of a fight, though, and while Waylon primarily remained in Nashville for the majority of his career, signed to major labels, he did play in Texas a lot, especially in the 70’s, and it will never cease to amaze me just how much they went through and were willing to lose to keep the integrity in their music and stay true to who they were as artists and people.

Their friendship last for decades, and now, their two incredibly talented sons Lukas Nelson and Shooter Jennings are working together in their professional endeavors, which is incredibly is an incredibly cool, full-circle moment for country music fans, and I’m sure an honor for them to carry on that legacy and do such an incredible job with it too.

Along with their timeless lyrics and once-in-a-generation voices, it’s safe to say we’ll never see another Willie Nelson or Waylon Jennings, but their story remains an inspiration for generations, and it all started in Tempe, Arizona.

“Mammas, Don’t Let Your Babies Grow Up to Be Cowboys”