A pioneer in the outlaw country movement, he put out some incredible music over the years, and always had a fascination with cowboys and that lifestyle.
So much so that, back in 1984, he headed to the Kokernot 06 Ranch in the Davis Mountains of West Texas to join the cowboys there for spring roundup. He documented the entire thing for the My Heroes have Always Been Cowboys film, and you can watch the entire thing YouTube.
They spent 10 days roaming the 250 square miles of the ranch, which is one of the largest privately owned ranches in the United States. It’s also one of the few remaining ranches where horses and cowboys still do cattle roundup work just as they did a century ago.
Of course, this being Waylon, he had some great insight and one-liners about his experience and why he was there:
“I always wanted to be a cowboy, I think everybody secretly dreams of being a cowboy, no matter where they’re from.”
But it wasn’t lost on him that it probably wasn’t the smartest thing to be doing, especially because he wasn’t a real cowboy and didn’t have a ton of experience on a wild horse:
“It strikes me that getting on a horse that’s half wild is maybe only half smart.”
Around the 20:30 mark, he plays an incredible fireside acoustic version of “Mammas, Don’t Let Your Babies Grow Up To Be Cowboys”.
And towards the end, when all the cowboys head to the local dive bar for a drink after a long day of work, he plays “My Heroes Have Always Been Cowboys” on a bar stool acoustically, which is absolutely captivating (46 minute mark).
Of course, he shared some final thoughts at the end of it as he loaded up on his tour bus to head back out on the road, saying that he learned a lot there, but the most important thing was this:
“Well, the roundup’s over. And I think I found out a lot of things about what a cowboy is… but most important, I found out what he ain’t. Me. But I still wish I was.”
If you need something good to watch this week, you can’t beat Waylon at cowboy school:
“Mammas, Don’t Let Your Babies Grow Up to Be Cowboys”
Waylon Jennings Once Asked Alan Jackson “What The Hell Is A Chattahoochee?”
You can always count on Waylon Jennings to tell is like it is, so when “Chattahoochee” hit country radio, he couldn’t help but ask Alan Jackson… what the hell is a “Chattahoochee?”
“I think Waylon said one time, Waylon Jennings, ‘what the hell is a Chattahoochee?’”
To be fair, unless you grew up near the Alabama/Georgia line, you’d probably have no idea as well. For those of you that don’t know, it’s actually a river that runs across northern Georgia, along the Georgia/Alabama border, and down into Florida.
And as it turns out, Alan was hesitant to release it as a single for the same reason.
“That’s why it was surprising to me when they decided to put ‘Chattahoochee’ out, I was reluctant because I said, ‘nobody is gonna know what that is.”
But according to Alan Jackson, Chattahoochee isn’t just a river, it’s a state of mind.
“The regular working people, the professional people, just trying to do the same things… make a living, raise a family, enjoy life… I learned that there’s a Chattahoochee everywhere.”
AKA, Chattahoochee isn’t just a river or a song… it’s a lifestyle.
When Waylon Jennings said, "What the hell is a chattahoochee?"