Willie Nelson: An Alleged 9-Hour Sex Session and 2-Person Backflip Inspired a $50 Million Lawsuit

As an original outlaw of country music, “Shotgun Willie” Nelson has been around long enough to tell some tales. But he’s also had a few incredible stories told about him. More specifically, a woman once alleged he broke a verbal engagement. And that was after nine hours of sex that ended in a two-person backflip. This seemingly too outrageous to be true accusation led to an attempt to extract $50 million from him.

“I’m not saying it didn’t happen,” Nelson said about the fable. But he also added, “You would’ve thought I’d remember at least the first four or five hours.”

So, what are a few of the facts behind the lawsuit that seemingly went nowhere? And what else has Nelson had to say about it?

Willie Nelson and the 1991 broken engagement lawsuit

In 1991, Vanity Fair wrote a story about Nelson that mentioned the unbelievable accusations in the lawsuit. As they explained, a woman accused the famous weed advocate “of breaching his verbal contract to marry her — claiming, among other things, that [Nelson] made love to her for nine hours straight in one session, concluding with a spectacular backflip.”

According to Rolling Stone, the $50 million lawsuit alleged the act was actually “consummated with a backward somersault with her still attached” — a noteworthy detail. It sounds pretty incredible, so what has Nelson had to say about it?

Willie Nelson once said this was ‘the only true story written about him’

In a 1991 interview, Nelson’s friend Kinky Friedman noted that Nelson once said the lawsuit’s allegation about an acrobatic rendezvous in the Biloxi, Mississippi, Hilton in 1985 was “the only true story written about him.”

However, he backed off that a bit when really pressed about the tabloid news story. “I’m not saying it didn’t happen,” he said to Friedman in their interview. “It might’ve. But you would’ve thought I’d remember at least the first four or five hours.”

“My ex-wife Shirley said she’d be glad to testify on my behalf,” Nelson shared, in the case that the lawsuit actually gained legal traction.

On a different but related note, Nelson writes in The Tao of Willie that Shirley once tied him to the bed and beat him with a mop handle. And that could have been because he’d secretly welcomed a child with his girlfriend.

But in the Vanity Fair article, it’s noted that he claimed his wife “Martha had literally sewn him up into the bedsheets before pounding on him with a whiskey bottle,” which she refuted. According to her, “She merely tied him up with jump ropes and beat him with a broomstick.”

But that sounds a lot like what Nelson said Shirley did. Whether one or two of his wives tied him up and beat him using things found around the house, it’s clear Nelson had a strange way with women. But speaking realistically, what are the chances the agile session in the Biloxi Hilton actually happened?

Willie Nelson was discharged from the Air Force for back problems in 1951

It seems unlikely that this Nelson story is actually true. Some of the details seem pretty improbable on their own, but Nelson was medically discharged from the Air Force after nine months in 1951. He had back problems which may have been related to picking cotton and bailing hay in his youth.

It’s hard to imagine he’d pull off such extraordinary feats at 52 after having back problems since youth. On the other hand, he did get a black belt when he was 81, and he took up yoga at some point.

But in the end, the lawsuit went nowhere, so a judge likely didn’t buy the story — even if the tabloids did.