Willie Nelson: Stories Of Legendary Outlaw/Bio Of Country's Beating Heart 

Music | April 29, 2020

Willie Nelson performs on stage at the Hammersmith Odeon in London, England in June 1982. (Photo by David Redfern/Redferns)

Willie Nelson, also known as The Ambassador to Weedville, Red Headed Stranger, and of course, Shotgun Willie, has enjoyed a life that lived up to his unforgettable nicknames. Some celebrities claim to have lived a crazy life full of wild tales and unbelievable adventures, but those celebrities aren't country-music outlaws. When Nelson is asked if the stories of parking lot shoot outs, smoking pot on the White House roof, and nine-hour sex marathons are true, Nelson usually shrugs and says maybe.

Amazingly, like John Wick, the stories of Willie Nelson over the years have only been watered down. Here’s to the truly stranger than fiction life of Willie Nelson.

It’s Not About The Money, But It’s Nice

Young Willie couldn't stay out of music for long (tripadvisor)

Over Nelson’s lengthy career money has never appeared to matter quite as much as having a good time. In fact, in 1972, he dropped $14,000 to buy himself out of his contract and retire to tranquil Austin, Texas. Naturally, as the Austin music scene heated up, Nelson couldn’t keep his guitar-playing fingers still for too long. Within a year he had a new LP (on a new label) in record stores, Shotgun Willie.

Willie Nelson Received A Bill From The IRS For $32 Million

Nelson sang his way out of debt (billboard)

Perhaps the best story regarding Nelson and his dismissal of money came when the IRS dropped a $32 million bill on his doorstep. Rather than take the Wesley Snipes approach and end up in jail, quick thinking Willie made a music deal with the IRS. Compiling demos, outtakes, and some tunes he had laying around, Nelson created the The IRS Tapes: Who’ll Buy My Memories? to pay his taxes.

Hilariously, when promoting the album, he wore a t-shirt that said 1-800-IRS-TAPE -- a toll-free number that went to a Salt Lake City-based technology company. Thankfully, the man loaned Nelson the number. The IRS Tapes eventually made $3.6 million and helped square him with the taxman. 

Willie Nelson Wasn't Afraid Of A Shootout

Gun touting Willie knew how to calm a firestorm (savingcountrymusic)

When Nelson found out his daughter’s husband, Steve was physically mistreating her, he showed up and beat some manners into him. He also warned Steve that “If he ever laid a hand on Lana again, I would come back and drown his ass.”

Well, Steve wasn’t very smart, and later showed up at Nelson’s home and started firing his .22. Nelson returned fire with his M-1 rifle, shooting out Steve's tire. Steve hightailed it away before calling the cops. Rather than explain the sordid affair, Nelson told the officers Steve must have driven over the bullet. As Willie said, "The police didn’t want to get involved in hillbilly family fights. They wrote down what I told them on their report and took off.”

Willie Nelson, Peacemaker

Willie Nelson living the American dream (star1025)

Amazingly, that was the tamer shootout Willie resolved. After a concert in Birmingham, Alabama, a woman started firing a .357 magnum in a 6 story parking garage as the band was loading up their gear. Nelson’s longtime manager tells the story best:

“Now here comes this bitch with a f**king pistol. ‘Kaboom!’ She’s chasing this motherf**ker. It sounds like a f**king war. Here come the cops from every direction. They’re flying out of their cars, hitting the parking deck, spread-eagling the whole crowd because the cops don’t know who is shooting at who."

"And here comes Willie. He walks off the bus wearing cutoffs and tennis shoes, and he’s got two huge Colt .45 revolvers stuck in his waist. The barrels are so long they stick out the bottom of his cutoffs. Willie just walks over and says, ‘What’s the trouble?’ Well, he’s got some kind of aura to him that just cools everything out. The cops put up their guns, the people climb off the concrete, and pretty soon Willie is signing autographs."

Hell Of A Friend

Nelson's always happy to share a joint with a friend (happymag)

When it comes to Willie Nelson stories, his joviality and calm, helpful demeanor always stand out. For example, the time he got Dennis Hopper out of a New Mexico jail, even though he never met Hopper before. Naturally, Hopper told it best:

I hadn’t got a clue how Willie knew I was in jail in Taos. At the time I couldn’t imagine how Willie Nelson even knew who I was.
In Taos, I had gotten real drunk and proceeded to win a lot of acid in a poker game, so I swallowed the acid and saw weird dangerous s**t going on, and I pulled my pistol out of my boot and shot up the plaza. Here came the sheriff saying Willie Nelson had come and paid my bill and was waiting outside.
I freaked f**king out. Willie Nelson? Come on, man, who do you think you’re kidding? You’re gonna lure me out and yell jailbreak and blow my ass away! But I thought, hey, be cool, you are after all hallucinating all this. So I walked out of jail and got into Willie’s Mercedes with him and his wife Connie and his golf pro Larry Trader. We drove across the desert towards Las Vegas. Willie and Trader and I nearly drove Connie crazy with our laughing and shouting.

Some Willie Nelson Stories Are Legends

Willie Nelson and Don Nelson, no relation, found a nice spot to retire to: Hawaii (Pinterest)

Only Nelson knows if these two stories are true but they are too good not to share. In 1980, Nelson was invited by President Jimmy Carter to play at the White House. After doing his thing, Nelson made it to the roof and lit up a joint. Nelson’s disdain for marijuana regulations are well known. So what better place to show your disregard for silly weed laws than smoking a joint on the Commander in Chief’s roof?

A woman sued Nelson for $50 million, claiming he promised to marry her. The woman also claimed that the couple had sex for nine consecutive hours, a sex marathon that was punctuated by a backward somersault with her still attached! When asked about the test of endurance, Willie said, “I’m not saying it didn’t happen,” he told Friedman. “It might’ve. But you would’ve thought I’d remember at least the first four or five hours.”

Today, Nelson enjoys that Maui Wowie lifestyle, growing his own strain called Willie Reserve on the Hawaiian Island and hanging with ex NBA coach Don Nelson. 

Tags: Country Music | Dennis Hopper | Marijuana | Outlaw Country | Rare Facts And Stories About History | Willie Nelson

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Kellar Ellsworth


Kellar Ellsworth was born and raised in Hawaii. He is an avid traveler, surfer and lover of NBA basketball. He wishes he could have grown up in the free love era!