Willie Nelson always seems so happy and mellow that it's hard to imagine that anything bad
ever happened to him.
As it turns out, though, he's more than equipped to play the blues every now and again because
behind that joyful facade hides a man who has dealt with his fair share of hard knocks.
Here's the tragic real-life story of Willie Nelson.
Willie Nelson has accumulated a number of nicknames over the years, but one of them
in particular 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 got physical with Steve, which led to a short gunfight after Steve subsequently
followed Nelson home and opened fire on his house.
Nelson grabbed an M1 rifle and returned fire, which drove the attacker away.
Steve then retaliated by kidnapping his and Lana's son and threatening to, in his words,
"get rid" of Nelson.
The singer decided to set up a trap, waiting for the attack with his rifle and yeah, you
guessed it his shotgun.
Nelson later described 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, releasing his album Shotgun Willie.
It's probably fair to imagine most country music stars being pretty politically conservative
but not Willie Nelson.
For one, the singer has his own cannabis product line called Willie's Reserve and even once
smoked a joint on the roof of the White House way back in 1980.
"And you have assigned yourself CTO is that correct?"
"Chief Tester."
"Yeah, ah, Chief Testing Officer."
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 little green
plant.
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 the Democrats.
He also made a point of noting that everyone has a right to an opinion, including himself,
and said that he personally doesn't mind even if supporters of Donald Trump enjoy his music.
If you're even superficially familiar with Willie Nelson's life, you'll probably be aware
that the man spent a good chunk of the 1980s and 1990s up to his armpits in tax trouble.
His long financial turmoil started in 1984, when the IRS discovered that Nelson's 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.
The 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 couldn't easily climb out of.
Nelson was unable to make significant payments as the years went by, which meant that his
debt kept accruing.
At the height of his tax troubles, Nelson owed the IRS an incredible $32 million.
On November 9th 1990, Willie Nelson's already shaky financial world came tumbling down.
This was the day the IRS finally grew tired of the singer's outrageous tax debt.
In an attempt to settle the score, federal agents seized pretty much everything the singer
owned.
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 took place.
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.
Luckily, losing all his earthly possessions didn't turn out quite as badly for Nelson
you might think, because the country star had a ton 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 then donating them right back to the artist.
Farmers, in particular, were extremely helpful, because they remembered the many millions
of dollars Nelson's Farm Aid concerts had raised for their industry.
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.
But Nelson still couldn't afford to pay.
In order to pay this outstanding debt, Nelson and the IRS 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
in part to one silly mistake: in one of the commercials for the tapes, Nelson was wearing
a shirt that featured the wrong phone number.
Fortunately, around this time, the singer's lawsuit with the accounting company that got
him in this whole mess in the first place was settled for an undisclosed sum, and he
became involved in a number of other lucrative projects.
The combined windfall over the next few years was enough for Nelson to finally pay the taxman.
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 can be extremely easy to give in to temptation.
Willie Nelson knows this well, and the singer has always been fairly open about his assorted
infidelities.
Nelson says that life on the road isn't exactly "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 is a veteran of three divorces, and they haven't all ended amicably.
For example, 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.
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 man himself:
"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."
As befitting a country singer, Willie Nelson has had his fair share of troubles with the
law.
But Nelson's arrests have been less about general outlaw trouble-making and more about...
well, exactly what you probably assume Willie Nelson might get arrested for.
"And by the way Willie Nelson’s the only person who’s ever out-smoked Snoop Dogg."
Yeah, no surprise there.
Between 1974 and 2010, the Red Headed Stranger was arrested four times on drug charges.
Unsurprisingly, marijuana possession seems to be his go-to charge, though in 2006 Nelson
decided to diversify by getting arrested for possession of 1 1/2 pounds of pot and over
three ounces of mushrooms.
The sheer amount of kush on him would have been more than enough to charge the country
star with a distribution felony, but luckily the four other people in the bus pulled a
Spartacus: Each of them claimed they owned the drugs.
Ultimately, law enforcement let them all off with a misdemeanor charge.
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 a bandmate, no less unexpectedly passes
away.
Sadly, 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 the lifeless body of the 62-year-old
musician was found the next day.
Reportedly, his cause of death was exposure.
As expected, Nelson was shocked and saddened by the loss of his longtime band member and
friend.
Willie Nelson turned 86 in 2019, but he's 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: his advanced
age and life on the road have meant all sorts of health scares for the singer.
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.
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.
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.
"I'm 85 years old so at some point you gotta start realizing, you know, how many more years
you wanna go."
They say art is pain, but Willie Nelson's experience with pain goes far beyond the emotional.
Instead, it's a very physical situation namely, carpal tunnel syndrome.
2004 was a particularly agonizing year for the country star, as his condition got so
bad that he had to call it quits part-way 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, 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.
Christmas Day in 1991 was one of the worst days in Willie Nelson's life because that
was the day when the singer's 33-year-old son Billy, a musician himself, was found dead
in his Tennessee home.
According to news reports at the time, he had taken his own life.
Billy Nelson had been struggling with alcohol abuse for quite some time, had been arrested
for drunk driving no less than four times, and did a stint in rehab in 1990.
Unfortunately, he failed to sober up, and was 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 life had been less than peaceful.
Still, Billy's death completely and utterly crushed Nelson.
After the tragedy, he said:
"I've never experienced anything so devastating in my life."
If you or anyone you know is having suicidal thoughts, please call the National Suicide
Prevention Lifeline at 1-800-273-TALK (8255).