The tragic real-life story of Willie Nelson

Willie Nelson has always been something of an oxymoron. He has somehow managed to take country music and marijuana advocacy, and stuff both in the perennially smiling body of an American icon. His "country" career has given the world many massive Billboard hits that feature collaborations with people as fabulous and diverse (and decidedly not country) as Ray Charles and Julio Iglesias. What's more, despite the fact that his back catalog features tearjerkers such as "Blue Eyes Crying in the Rain," the man himself seems like one of those celebrities who are so perennially happy and mellow, it's hard to imagine that anything bad has ever happened to him — definitely not enough to warrant an article about his "tragic real-life story." 

Then again, that's only because you haven't read the rest of the article yet. Appearances can be seriously deceiving, and it turns out that the Red Headed Stranger is more than equipped to play some sad, sad country — because in reality, the legendary performer's joyful facade hides a whole host of hard knocks that life has dealt him over the decades. Come, let's take a look at the tragic real-life story of Willie Nelson. 

Shotgun Willie is more than just the name of an album

Booger Red. Ambassador to Weedsville. Red Headed Stranger. Willie Nelson has accumulated a number of nicknames over the years, but one of them seems pretty out of character: Shotgun Willie. The official website of Willie Nelson and Family has the story behind the unlikely moniker, and it very much involves a real shotgun. Back in the day, Nelson's daughter Lana was married to a violent man called Steve. One day, Nelson "slapped Steve around" for his misdeeds, which led to a short gunfight when Steve followed Nelson home and opened fire at his house. Nelson grabbed a M1 rifle and returned fire, which drove the attacker away.

Steve retaliated by kidnapping his and Lana's son and threatening to "get rid" of Nelson. The singer decided to set a trap, waiting for the attack with his rifle and — everybody together now — shotgun. Here's how Nelson describes the incident: "He drove by the house, and I ran out the garage door. Steve saw me and took off. That's when I shot his car and shot out his tire. Steve called the cops on me. Instead of explaining the whole damn mess, the beatings and the semi-kidnapping and shooting and all, I told the officers he must have run over the bullet."   

In 1973, Nelson took the nickname and ran with it with an album called Shotgun Willie. It was an excellent record Rolling Stone calls "flawless," which probably didn't hurt making the nickname stick. 

Willie Nelson's political backlash

If you imagine an average country music star, you might assume that they're politically conservative. Willie Nelson, on the other hand, has his own cannabis product line called Willie's Reserve. Esquire notes that the Red Headed Stranger has smoked a joint on the roof of the White House (way back in 1980, no less!) He has also written an anti-Trump protest song, and is well known for supporting gay marriage, environmental causes and, of course, the legalization of a certain plant. All in all, it's almost like he might lean toward the liberal side of things. 

Despite all this, Nelson managed to court controversy in 2018 when his fans found out he was supporting Democrat Beto O'Rourke's Senate campaign. Conservative country fans were outraged when Nelson not only invited O'Rourke onstage during a concert, but even agreed to headline a rally for the candidate. Soon, many of Nelson's Republican-leaning fans were voicing their anger and disappointment on social media, stating that they couldn't enjoy the artist anymore and even attempting to sell tickets they'd bought to his shows. 

Nelson himself took the outrage in stride, and noted that he has never really hidden the fact that he supports Democrats. He also made a point of noting that everyone (including him) has a right to an opinion, and said that he personally doesn't mind if, say, supporters of Donald Trump enjoy his music. 

Willie Nelson and the accounting company

If you're even superficially familiar with Willie Nelson's life, you might be aware that the Red Headed Stranger spent a good chunk of his 1980s and 1990s up to his armpits in tax trouble. According to Forbes, his long financial turmoil started in 1984, when the IRS discovered that Nelson — or rather, as the musician himself claimed, his accounting company Price Waterhouse — had been using tax shelter investments to claim some pretty hefty deductions. Nelson promptly took the accounting firm to court, but the damage had already been done. IRS slapped the artist with a massive tax bill and an assortment of penalties and interest, which along with a second tax bill plunged him into a pit of debt even one of the most famous country musicians in the world could not climb out of. 

Nelson was unable to make significant payments as years went by, which meant that his debt kept accruing. In fact, Rolling Stone tells us that at the height of his tax troubles Nelson owed the IRS a ridiculous $32 million. 

The IRS seized Willie Nelson's earthly possessions

On November 9, 1990, Willie Nelson's already shaky financial world came tumbling down. As Rolling Stone tells us, this was the day the IRS finally grew tired of the singer's outrageous tax debt. In an attempt to settle the scores, federal agents seized pretty much everything the singer owned: His properties across six states, master tapes, platinum and gold records, even clothes. He only managed to save his most prized possession, the beloved guitar he called Trigger, because his daughter managed to send it to Maui before the raid. For a while, the situation was so bad that Nelson didn't even dare perform live for fear that the taxman would take the door receipts. 

According to Forbes, losing his earthly possessions was not quite as bad for Nelson as it sounds like, because the country star had oodles of friends and fans who were aware of the situation and reacted to the auction of his belongings by buying a whole bunch of his assets and donating them right back to the artist. People notes that farmers, in particular, were extremely helpful, because they remembered the many millions of dollars Nelson's Farm Aid concerts had raised. 

Unfortunately, Nelson still owed the IRS something along the lines of $16.7 million.  Fortunately, his lawyer was eventually able to negotiate it down to "just" $6 million. Unfortunately again, Nelson still couldn't afford to pay. 

Willie Nelson and the IRS Tapes

As Forbes reports, even after the IRS took away his properties and his lawyer had negotiated as much of the remaining debt away as possible, the virtually broke Nelson still owed $6 million. According to Rolling Stone, Nelson started appearing in ads to clear the debt. The musician and the agency also teamed up for a peculiar plan to raise money: Nelson sold an appropriately somber, two-disc collection of acoustic versions of his songs in an infomercial, and a chunk of the proceedings would go directly to the IRS. Nelson, who kept his sense of humor throughout the ordeal, even named the album The IRS Tapes: Who'll Buy My Memories?

The album sold fewer units than anticipated and failed to settle Nelson's debt, thanks to a ridiculous mistake: he appeared in the commercial wearing a shirt that featured a wrong phone number. Fortunately, around this time, the singer's lawsuit with the accounting company that got him in this mess in the first place was settled for an undisclosed sum, and he became involved in a number of lucrative projects. The combined windfall over the next few years was enough for Nelson to finally pay the taxman. 

Willie Nelson's infidelity issues

When you're a famous singer who tours the country pretty much non-stop and has adoring fans surround you on a nightly basis, it's extremely easy to give in to temptation. Willie Nelson knows this well, and as Pop Culture tells us, he's always been fairly open about his assorted infidelities. 

Nelson says that life on the road isn't "healthy for marriages," and he has the ex-wives to prove it. One particularly nasty example of the Red Headed Stranger's infidelities impacting his marital life came in 1971, when Nelson's wife Shirley Collie received a letter that contained the bill for the birth of a baby called Paula Carlene Nelson. This was all fine and dandy, except for one minor issue: Collie hadn't given birth to any baby recently. The mother was actually one Connie Koepke, and the hospital had billed the wrong woman by accident. Suffice to say, Nelson's marriage with Collie didn't last too long after that.

Willie Nelson's multiple divorces

According to Pop Culture, Willie Nelson's a veteran of three divorces, and they haven't all been nice. The Telegraph tells us his first wife left him because of his hard-drinking ways, and gave him the parting gift of "tying him up in a sheet and beating him with a broom." Even more infamously, his second wife found out about his soon-to-be third one after opening a letter that concerned a child that was Nelson's, but definitely wasn't hers. 

According to his official website, Nelson remains somewhat unapologetic about his many ended marriages, and has been known to say that divorces are expensive for a reason: They're worth it. Despite this, he doesn't demonize his ex-wives or, for that matter, even really think of them as "ex-wives." According to the Red Headed Stranger, "Along the way you pick up wives and kids and you are responsible for them. You don't discard them. There is no such thing as ex-wives, only additional wives."

Willie Nelson and the law

As befits a country singer, Willie Nelson has had his share of troubles with the law. As Business Insider tells us, however, Nelson's particular arrests have been less about general outlaw trouble-making and more about … well, exactly what you probably assume Willie Nelson might get arrested for.  

Between 1974 and 2010, the Red Headed Stranger has been arrested four times for drugs, which means there are actually mug shots of the guy that were taken 36 years apart. Unsurprisingly, marijuana possession seems to be his go-to charge, though The Boot reports that in 2006 the Red Headed Stranger decided to diversify by getting arrested for possession of 1 1/2 lbs. of pot and over three ounces of mushrooms. The sheer amount of kush would have been more than enough to charge the country star with a distribution felony, but the four other people in the bus pulled a Spartacus: Each of them claimed they owned the drugs. Ultimately, the law enforcement let them all off with a misdemeanor charge.  

Willie Nelson and the death of Dan "Bee" Spears

As Texas Monthly reports, Willie Nelson is extremely fond of his entourage, which he tends to think as something of an extended family. Imagine, then, his pain when one of these people unexpectedly dies, especially when said person happens to be an actual bandmate who has been a part of Willie Nelson and Family for over 40 years. 

According to Rolling Stone, this exact scenario played out in 2011, when Nelson's longtime bass player Dan "Bee" Spears was stepping out of his motor home near Nashville, Tennessee, and unexpectedly slipped and fell. Details about the events that followed are scarce, but Lone Star Music Magazine tells us that the lifeless body of the 62-year-old musician, who played on some of Nelson's most famous albums, was found the next day. Reportedly, his cause of death was exposure. As expected, Nelson was "in shock" and "deeply saddened" by the loss of his longtime band member and friend. 

The death of Willie Nelson's son

Christmas Day in 1991 was one of the worst days in Willie Nelson's life. According to People, that was the day when the singer's 33-year-old son Billy, a musician himself, was found dead in his Tennessee home. AP News reports that he had hanged himself with a cord. Billy Nelson had been struggling with alcohol abuse for quite some time. He had been arrested for drunk driving no less than four times, and had done a stint in rehab in 1990. Unfortunately, he failed to sober up, and was indeed legally drunk the night he died.

Nelson kept in touch with Billy and provided him with an allowance, and Billy's good friend said that the musician did all he could for his son. However, Nelson himself has admitted that he was often on the road during Billy's childhood, and a family friend heavily insinuated that Billy's existence had been less than peaceful. Still, regardless of the quality of his fatherly duties, Billy's death completely and utterly crushed Nelson. "I've never experienced anything so devastating in my life," he said about the tragedy.   

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline at 1-800-273-TALK (8255).

Willie Nelson's health scares

Willie Nelson turned 86 in 2019, and is still very much in the touring game. Whether this is a display of truly exceptional work ethic or merely a man doing what he loves as long as humanly possible is up for debate, but one thing is tragically certain: Advanced age and life on the road equal all sorts of potential health scares. 

As Rolling Stone reports, one such scare occurred in August 2019, when Nelson abruptly canceled the remaining 30 shows of his tour because of a "breathing problem" that required a doctor. Fortunately, this particular issue was either quickly solved or deemed insignificant, because Nelson's publicist soon announced that he will resume the tour after all. However, this is hardly an isolated event. As Taste of Country notes, Nelson has been struggling with emphysema for several years, and show cancellations and rescheduling have been common. In 2017, another bout of "respiratory issues" forced him to stop a concert short in Salt Lake City. While he blamed the altitude for that particular incident, it would not be his last one. In 2018, a "devastating" flu took Nelson's February tour dates off the calendar, and a few months later he had to walk off stage without playing a note. It remains to be seen how long his body will allow him to keep performing.  

Willie Nelson's battle with carpal tunnel syndrome

Art is pain, they say, and Willie Nelson has some personal experience with the subject. His particular pain is not (just) the proverbial heartbreak usually associated with that particular saying, though. Instead, it's a very physical situation — namely, carpal tunnel syndrome. Not great when your job is playing guitar.

As CBS News reports, 2004 was a particularly agonizing year for the country star, as his condition got so bad that he had to call it quits partway through a concert in Las Vegas. The pain was so excruciating that he had to cancel two months' worth of concerts in order to fix his carpal tunnel syndrome with surgery, and while he was able to pick up his guitar again, the Globe and Mail notes that his struggle with the problem has been a long one. In fact, carpal tunnel syndrome may even have affected Nelson's peculiarly "jazzy" and "avant-garde" playing style, much like his idol Django Reinhardt had to develop his peculiar style because two of his fingers were paralyzed. Hasn't stopped the "Pope of Puff" from being voted the "77th greatest guitarist of all time," though.