If there was ever a story that perfectly captured Waylon Jennings’ outlaw spirit — equal parts rebellious, ridiculous, and romantic — this is it.
After years of battling addiction, Waylon finally made the life-changing decision to get sober. It wasn’t fame that pushed him there. It wasn’t pressure from Nashville. It was a moment with his young son, Shooter, that broke his heart and made him realize he needed to change.
And when he did?
He decided to celebrate in true Waylon fashion.
The object of celebration was a gold Cadillac — flashy, unapologetic, and larger than life. According to Waylon, he first saw the car in Phoenix shortly after quitting drugs. With his trademark humor, he later joked that the nose of the Cadillac reminded him of what he had just left behind — “take it out of one nose and put it in another.”
But the real reason he bought it was Shooter.
At just four years old, Shooter looked at the car and said, “Dad, I like that, let’s buy it.” That was enough for Waylon.
When he turned the key and heard one of his own songs playing on the radio, he took it as a sign. An omen. The deal was sealed.
Now here’s where it gets legendary.
Waylon decided he wanted to pay in cash — over $40,000 worth. And instead of carrying it in a briefcase like a normal person, he asked Jessi Colter to stash the money in her bra.
She agreed.
The two walked into the dealership, unaware that two preachers and their wives were also in the room. When the salesman asked how he’d like to pay, Waylon casually replied, “Cash.”
Then he started reaching into Jessi’s bra… pulling out stacks of bills.
According to Waylon, he would occasionally pinch her, making her squeal, while the stunned onlookers watched in disbelief. It was outrageous. It was theatrical. It was absolutely on-brand.
Later, Jessi reminded him just how much money she had been carrying — over $40,000. Waylon shrugged it off. The point wasn’t the amount. The point was the moment.
He paid cash for the car. Jessi stood by his side. And together, they drove off in that gold Cadillac — a symbol not just of excess, but of a new chapter.
Behind the humor and chaos, there was something deeper.
Jessi believed in him. She stood by him through addiction, fame, and reinvention. When Waylon finally chose sobriety, she didn’t just support him — she celebrated with him.
“Partners in crime,” he once said.
And in that dealership, reaching for stacks of cash while a room full of shocked witnesses looked on, they proved it.