The True Story Behind The Wrangler Ad Campaign That Featured Willie Nelson Lighting One Up With Dale Earnhardt Sr. And Richard Childress

Willie Nelson Dale Earnhardt

There are TWO legendary birthdays to celebrate today.

And my own personal opinion is that it’s no coincidence…

The one and only Willie Nelson is celebrating his 89th with the released of a brand new album, A Beautiful Time, and the late, great Dale Earnhardt Sr. would’ve only been 71 years old today.

And back in the 80’s, the two icons joined car owner Richard Childress (who Dale Sr. drove for) to participate in an advertising campaign promoting Wrangler jeans.

They shot it in San Francisco, and a few years back at a Wrangler event in Greensboro, North Carolina, Richard told Fox Sports the story of how it all went down.

And it pretty much happened exactly the way you’d imagine, and is quite possibly the best story I’ve ever heard:

“I came in from hunting in British Columbia and Dale and I ate at one of those really neat seafood restaurants there (in San Francisco). We got up early the next morning for the photo shoot.

Dale and I were sitting there waiting, I was expecting Willie to come out with a cowboy hat and everything.”

He actually showed up in a Member’s Only jacket, which is just hilarious (and awesome):

“He came out with a baseball hat on and wearing a black Member’s Only jacket. That was his disguise back in the day.

So he jumps in the limo and we shake hands. That was the first time I had met him. I’m not sure if it was for Dale.

Though Willie didn’t show up in full-on Texas cowboy garb, he did have his signature accessory on hand:

“But he sat over there and fired up a joint, and started smoking on his joint. He leaned over (as if to offer it to his fellow passengers) and Dale said, ‘No, we’re going to drink some whiskey later.’

But that’s the story behind that photo shoot right there. That’s why he’s smiling.”

Willie lighting one up and Dale and Richard downing the whiskey on set with Wrangler? You absolutely have to love it.

I cannot think of a more on-brand scenario for all parties involved here, and I only wish I could’ve been a fly on the wall during this whole day.

Of course, Dale Earnhardt Jr. was so young at the time that he didn’t think of his dad as a celebrity, and was mainly just excited their family was collaborating with Willie Nelson for such a cool project, which also featured some more advertising to help promote Willie’s tour at the time:

“Dad had ‘One tough customer’ on the back of the car and they were cross-promoting that with Willie’s tour. So it was a pretty neat deal for me at that age.

I didn’t look at dad as famous or any sort of celebrity… We were all pretty giddy that Willie Nelson was involved in anything we were doing.”

The slogan for the whole Wrangler photo campaign was “Winners wear Wranglers,” and with that and all the iconic photos that came from it, I’d say they pretty much nailed it.

I haven’t seen a better one since…

Check out some of the super cool footage of Dale Sr. with all the Wrangler sponsorship that coincided with this ad campaign back in the day and that iconic yellow car:

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