Waylon Jennings Had Jessi Colter Bring $40,000 Worth Of Cash In Her Bra To Buy His Iconic Gold Cadillac: “I Started Reaching In & Pulling Out Money”

Partners in crime, indeed.

Waylon Jennings was known as the ultimate outlaw man, and he had a life that backed that up… especially before he quit his years-long drug habit. It was after he had met his wife Jessi Colter and his son Shooter that he finally kicked the habit for good.

Jessi and Waylon met in the ’60s in Arizona at JD’s nightclub, and in October of 1969, they got married and moved to Nashville. Waylon continued to struggle with his drug addiction, and Jessi wanted badly for her husband to quit them, obviously, but she also understood that he needed to do so in his own time and way.

That dream eventually came true after Waylon had a heartbreaking moment with his very young son Shooter, and to celebrate his newfound sobriety, Waylon decided to buy a gold Cadillac mostly because Shooter wanted him to. The car was also featured in his “America” music video, but the story behind the buying process is just hilarious and SO Waylon.

He wanted Jessi to go with him, and since he was paying in cash, he wanted her to put it in her bra and he would pull it out at the dealership, as he explained in a vintage interview from 1994 with TNN:

“Well, I got that one, I was in Phoenix and I had just quit drugs. Now the nose of that Cadillac, and I saw that, and figured, well, take it out of one nose and put it in another. So I bought that Cadillac. Actually, why I bought it was Shooter. He looked at it and said, ‘Dad, I like that, let’s buy it.’ Shooter was four years old, that’s a cool car.

Now, another thing is, I got in and turned the key and started it and the radio came on and was playing one of my records. I said, if I used car sales and can arrange that not knowing I’m coming over here, then I gotta buy the car. So it was an omen. And I thought how funny it would be to pay cash for a car, you know, and get Jessi to carry the money in here.”

Well, she stuffed $40,000 worth of cash in there, though they didn’t expect to be in the room with two preachers and their wives also in the room, and Waylon admitted he would “pinch her and she would squeal,” so they caused quite a scene and I’m sure no one in there had ever seen anything like that before… just classic:

“So me and my buddy, Jessi Colter, went in there, and I didn’t know, but there were two preachers and their wives were there and they had all kinds of people around that I didn’t know. And he said, ‘How would you like to pay for this?’ And there’s that gold Cadillac, and I said, ‘Cash.’ And I started reaching in there, inside her bra and pulling out this money.

Every once while I’d pinch her and she would squeal. But on the drive she said, ‘You know, that much, over $40,000 is what you had.’ That didn’t make much difference… there’s not enough money there. But I paid cash for it, and Jessi helped me. Partners in crime, we are.”

They really were, and I can just picture how funny that moment had to have been, and I’m sure it was something no one who witnessed it ever forgot, that’s for sure. It’s also something you could probably only get away with if you’re Waylon Jennings and Jessi Colter, but I think it’s hilarious and she’s a good woman for going along with his antics and indulging him like that.

They had such a beautiful love story, and she believed in him and loved Waylon unconditionally until the end… you can watch Waylon tell the story below, and I highly recommend doing so:

And if you want to see the car in action, check this out:

“America”

The post Waylon Jennings Had Jessi Colter Bring $40,000 Worth Of Cash In Her Bra To Buy His Iconic Gold Cadillac: “I Started Reaching In & Pulling Out Money” first appeared on Whiskey Riff.