Outlawed Facts About Willie Nelson, The Red Headed Stranger

October 24, 2020 | Eli Artman

Outlawed Facts About Willie Nelson, The Red Headed Stranger

Willie Nelson is not only one of the most iconic stars in the world of country music, he is also one of America’s best-known entertainers in any musical genre! But as universally known and loved as he is today, the road to stardom and success was a long and rocky one for Nelson—full of ups and downs that might shock those who are unfamiliar with the singer’s life story. From the sad to the amazing, here are 50 fascinating facts about the one and only Willie Nelson.

Willie Nelson Facts

1. He Has Two Birthdays

Willie Nelson’s life began in Abbott, Texas on April 29, 1933—or at least that’s one version of the story. A mishap caused confusion over which date he was actually born on since the hospital staff completed their paperwork after midnight. On the bright side, Nelson deals with this problem by celebrating his birthday for two days straight every year.

Willie Nelson FactsWikimedia Commons, Bob Jagendorf

2. He Could Already Write Songs As A Child

Willie Nelson took the concept of “starting young” to a whole new level. He composed his first original song when he was only seven years old. Despite being way too young to have ever experienced a relationship, let alone a breakup, the song was about the sorrow of a man whose lover left him for someone else.

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3. He Started In A Different Musical Genre

Nelson’s first job as a professional musician came from an extremely unlikely source. Beginning at the age of nine, Nelson worked as the guitarist for a polka band known as Bohemian Polka. Although Nelson’s grandmother did not approve of the drinking that went on at the group’s shows, she allowed the young musician to pursue his dreams without objection.

Willie Nelson FactsGetty Images

4. He Had Many Interests Outside Of Music

Even if Willie Nelson hadn’t been interested in music, he probably would have found some other fun alternative to pursue. His extracurricular interests in high school included football, basketball, baseball, and farming. He also worked all kinds of odd jobs, including as a phone operator, tree trimmer, pawnshop employee, nightclub bouncer, saddle maker, garage employee, and dishwasher.

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5. He Served His Country

When he completed high school, Nelson enlisted in the United States Air Force and served for a period of about eight months in 1950. However, the medical staff soon discovered that Nelson suffered from back problems and they decided to discharge him from service as a result. And so ended the short chapter of Nelson’s life in uniform.

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6. He Had A Wild Cross-Country Adventure

After moving around for a few years and trying out different jobs, Nelson wanted to join his mother in Portland, Oregon. Without any money or plans, he hitchhiked on the side of the road. No one stopped for him, so he spent the night sleeping in a ditch. The next day, he snuck onto a freight train and rode it as far as he could.

Eventually, a kind-hearted truck driver lent Nelson a few bucks for a bus ride the rest of the way and he made it safely to his destination.

Willie Nelson FactsPixabay

7. He Started A New Career

After some initial failures in the music business, Nelson tried to move on with his life. He started a new career as a door to door salesman. After finding some success selling both Bibles and vacuum cleaners to local homeowners, the singer eventually found his way to a job as a sales manager for an encyclopedia company. But music was still calling to him…

Willie Nelson FactsGetty Images

8. He Taught Music Lessons

Once he started singing for bar crowds, Nelson officially caught the music bug again. He got a new job in the radio business and also spent some time as a guitar teacher at a local music school. That means that there are some lucky folks out there who were taught by a musical icon and might not even have realized it!

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9. He Finally Made A Breakthrough

Although no one seemed interested in him as a singer in his early years, Nelson finally caught a break when country star Faron Young heard him perform his song, “Hello Walls.” The star liked the song enough to record a version of it. After that, legendary artists such as Roy Orbison, Patsy Cline, and Billy Walker recorded some of Nelson’s original songs as well.

Willie Nelson FactsFlickr


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10. He Had A Violent Spouse

Nelson has seen his fair share of heartbreak and tragedy in his life. He has been married four times, and some of these relationships were very rocky. His first wife, Martha Mathews, treated Nelson horribly and even physically assaulted him on multiple occasions. But the story of their relationship still gets so much crazier than that…

Willie Nelson FactsShutterstock


11. His First Wife Went Diabolical On Him

On one occasion, Mathews took her marital violence to a whole new level. She sewed a sheet to Nelson’s bed while the singer was stuck in place underneath it. She then proceeded to mercilessly and repeatedly beat him with a broomstick, while her trap kept him unable to move. That’s some next level crazy right there!

Willie Nelson FactsPixabay

12. One Of His Iconic Songs Almost Didn’t Happen

Patsy Cline’s recording of Nelson’s “Crazy” is undoubtedly the highlight of his early career—yet it almost never came to be. Cline’s husband had heard Nelson sing an early draft of the song at a bar. He decided it would be perfect for his wife to sing. But there was just one problem—Cline hated the song and thought that Nelson’s singing style was too strange to try and copy.

Eventually, her husband convinced her to record it in her own style, and a classic was born.

Patsy Cline Facts Wikimedia Commons

13. His House Got Destroyed

As Nelson’s career continued, he moved into a new home—a quiet Tennessee ranch a little bit outside of Nashville. But one day, when he returned home from a Christmas party, he made a disturbing discovery—the house was completely ablaze. Before that day came to a close, the house had burned to the ground, leaving Nelson homeless.

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14. He Risked His Life For An Unexpected Reason

As his house was on fire, Nelson rushed inside to try and rescue a precious possession—his stash of pot. This may sound funny on the surface, but his reason was actually quite serious. Nelson feared that if the firemen saved his home and found the substance inside, then they would have turned him over to the authorities to face consequences.

Willie Nelson FactsWikimedia Commons

15. He Thought His Career Was Over

Frustrated with how his career was going, Willie Nelson finally decided to call it quits. He bought out his own contract and retired from music in 1972. He moved to Austin, Texas to escape the Nashville lifestyle and the business that he had dealt with for almost two decades by this point. Little did he realize that his true musical career had still not yet begun…

Willie Nelson FactsNeedpix

16. He Reset His Career

Inspired by Austin, Nelson abandoned the traditional styles of Nashville and developed the unique sound that we all know and love him for today—and it changed his career. He returned to recording in 1973 and released his first-ever critically-acclaimed album, Shotgun Willie. The album reset Nelson’s career and set the foundation for his new “outlaw country” style.

In Nelson’s own words, creating this album “cleared his throat.”

Willie Nelson FactsWikimedia Commons


17. He Finally Made It

By now, it was only a matter of time until Nelson would have a breakout record take the world by storm. That finally happened in 1975 with the release of the Red Headed Stranger concept album, which would go on to become one of the most popular country albums of all time. At the age of 42, this unique album finally launched Nelson into the realm of superstardom.

Willie Nelson FactsGetty Images

18. His First Big Hit Was A Cover

In addition to its compelling outlaw-themed narrative, the Red Headed Stranger album also gave us Nelson’s first-ever number one hit as a singer. Ironically, after all those years as a successful songwriter, his first chart-topper was a cover of “Blue Eyes Crying in the Rain”—an old, long-forgotten Fred Rose song from the 1940s.

Willie Nelson FactsWikimedia Commons

19. He Had Problems With His Manager

In 1977, scandal hit Nelson’s inner circle. He fired the manager who oversaw his rise to fame after federal agents intercepted a package from him containing illicit substances. The package had been en route to the office of Waylon Jennings, Nelson’s good friend and frequent singing partner. Nelson also accused this manager of mishandling his money and defrauding the IRS.

Willie Nelson FactsFlickr

20. He Broke A Promise

We’ve only scratched the surface so far when it comes to the craziness of Nelson’s relationships. At one point in his life, an ex-girlfriend of the singer sued him for a whopping $50 million. She argued that breach of contract laws should be applied to punish Nelson for promising to marry her and not following through.

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21. He Has A Lot Of Energy

Although the lawsuit against Nelson did not get very far in court, it did reveal some incredible details about what allegedly took place between the singer and this ex-girlfriend during their relationship. Apparently, the pair once had a lovemaking marathon which lasted for no less than nine hours straight!

Willie Nelson FactsShutterstock

22. He Could Have Been An Acrobat!

As if the nine-hour marathon isn’t crazy enough in and of itself, this story still gets so much crazier! Apparently, for the grand finale of this marathon, Nelson had somehow maneuvered a full-blown somersault with his girlfriend’s body still attached to his. Now that is an image you definitely can’t unsee once you’ve tried to picture it!

Willie Nelson FactsWikimedia Commons


23. He Had A Hidden Talent

Wilson’s next big success came from an unlikely source. After a lifetime of work in the country genre, Nelson decided to change it up and record an album of his favorite old-time jazz standards. His record company advised against going forward with the project, insisting that the drastic change in style would result in a flop.

Nevertheless, Nelson persisted and the resulting Stardust album became one of his most popular releases ever.

Willie Nelson FactsWikimedia Commons

24. His Signature Song Had A Wild Origin

In 1980, Nelson released one of the biggest hits of his career, “On The Road Again”—but it came about in a crazy way. The idea for the song came to Nelson while he was on a flight. Not wanting to forget the lyrics he was coming up with, he grabbed whatever he could find to quickly scribble them down. Turns out he wrote the entire song on the back of a barf bag!

Willie Nelson FactsShutterstock

25. He Was Unfamiliar With His Own Masterpiece

Another of Nelson’s most iconic songs of all time is his version of “Always On My Mind.” This song was not an original composition of Nelson’s, nor did he record it because he was a fan of Elvis Presley's famous version of it. In fact, Nelson was actually completely unaware of the song or its pre-existing fame when he first decided to record it. The famous recording came to be in a totally unexpected way…

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26. Eavesdropping Led To Making History

It all started when one of the song’s co-authors was hired as a back-up musician for a session Nelson was doing with fellow country star Merle Haggard. The guitarist thought that Haggard could do wonders for his song, and he tried unsuccessfully to sell him on the idea. But Nelson overheard this pitch and agreed to record the song himself, winning three Grammy Awards in the process.

George Jones FactsWikimedia Commons

27. He Teamed Up With The Elites of His Genre

Nelson helped put together the most epic supergroup in country music history, “The Highwaymen.” The group consisted of four outlaw country superstars—Nelson himself, Johnny Cash, Waylon Jennings, and Kris Kristofferson. Together, they released three albums and even had a number one song in 1985 called “Highwayman.”

Willie Nelson FactsGetty Images

28. He Has Friends In High Places

President Jimmy Carter and his wife, Rosalynn, have always been big fans of Nelson’s, and they invited him to perform for them at the White House in 1980. After the performance, Nelson snuck onto the White House roof to smoke pot! Despite this stunt, Nelson and Carter developed a lifelong friendship and even performed “Amazing Grace” together in 2012.

Willie Nelson FactsGetty Images

29. He Has Mastered Non-Musical Interests Too

Nelson has been interested in martial arts since childhood. He ordered jujitsu and judo training manuals after seeing them advertised in superhero comic books, and he has been hooked on the hobby ever since. He holds a second-degree black belt in taekwondo and has also formally practiced kung fu and GongKwon Yusul.

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30. His Guitar Is The Love Of His Life

Nelson has played the same guitar for more than fifty years. He named it “Trigger,” after cowboy Roy Rogers’ famous horse. Trigger is famous for its battered appearance, the large hole in the middle of it, and the countless autographs that have covered its body over the years. Nelson has gone to great lengths over the years to protect Trigger—even hiding it from auditors and running into a burning building to rescue it.

Willie Nelson FactsWikimedia Commons

31. He Created A Charitable Institution

In 1985, Nelson helped set up Farm Aid—a major annual charity concert to help struggling families in the American farming industry. The event raised more than nine-million dollars in its first year, and has been held every year since. Celebrities who have participated in the event over the years include Roy Orbison, Bob Dylan, B.B. King, Billy Joel, and Tom Petty.

Willie Nelson FactsGetty Images

32. Tax Issues Destroyed His Finances

Due to a combination of mismanagement, poor advice, and bad investments, Nelson wound up with a nasty surprise in the early 90s. He owed the IRS more than $32 million in unpaid taxes and fines. Even for a top-selling artist, paying off that kind of a debt is no small task. As a result, the government seized almost all of the singer’s personal assets.

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33. He Did Everything Imaginable To Fix The Problem

To help raise money to pay off his enormous debts to the government, Nelson released a double album titled The IRS Tapes: Who’ll Buy My Memories? He also auctioned off some of his remaining belongings and sued several of the people who he blamed for getting him into this nightmarish situation. Some of his friends also chipped in to try and help.

Willie Nelson FactsFlickr, Mark Runyon

34. He Had A Bit Of A Mishap

Hoping to garner public help for his tax situation, Nelson appeared on TV wearing a T-shirt that displayed the phone number “1-800-IRS-TAPE.” There was only one problem. Nelson somehow hadn’t realized that this phone number belonged to some random guy’s unrelated technology business in Utah. Luckily, rather than getting angry at the singer for tying up his phone lines, the business owner gave the phone number to Nelson.

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35. He Lost A Child In A Tragic Way

Tragedy struck the singer’s family in 1991 when one of his children, Billy Jr., took his own life at the age of 33. Billy had been struggling with a drinking problem, which may have played some role in the tragedy. Nevertheless, this development came completely out of the blue and completely shocked all those who had known him.

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36. His Spirituality Healed His Broken Heart

The news of his beloved son’s passing devastated Willie Nelson, as one would fully expect it to. On the bright side, however, the singer managed to get through this dark period by finding solace in his spiritual belief in reincarnation. This belief allowed him to feel that he would some day meet his son again, despite how dark things seemed in the moment.

Willie Nelson FactsWikimedia Commons

37. He Was In A Plane Crash

Many years ago, while en route to meet Western movie legend Happy Shahan, Willie Nelson was involved in a terrifying accident when the small plane he was in violently crashed. Those awaiting his arrival witnessed the crash and feared the worst. However, by the time reporters and potential first responders arrived on the scene, they made a shocking discovery.

Plane Crashes factsShutterstock

38. He Got The Last Laugh

As reporters approached the destroyed plane, they expected to find Nelson either gravely injured or already gone. Instead, they got the shock of their life when they saw Nelson and his pilot alive and well, limping away as if nothing had even happened. When asked if he was alright, Nelson’s reply was unforgettable. He casually remarked “This was a perfect landing. I walked away from it, didn’t I?”

Willie Nelson FactsGetty Images

39. He Fights For What He Believes In

Nelson has been a leading pot activist for many decades, and has long campaigned for the substance to be legalized. He serves on the board of a national advocacy organization that deals with this subject, and he has a lot of personal experience with the effects of the existing laws. As a lifelong pot user, Nelson has faced multiple arrests for possession-related offenses—including as recently as 2010, when he was close to 80 years old.

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40. He Sued His Own Political Party

Despite being a frequent supporter of the Democratic Party and its representatives, Nelson sued the party in 2008. A dispute over their candidate selection process resulted in the party disqualifying his preferred candidate from Texas ballots. Nelson claimed that requiring candidates to pledge a loyalty oath to the party was a violation of constitutional rights.

Willie Nelson FactsShutterstock

41. He Turned His Passion Into A Business

Nelson has his own line of commercially available pot, which he sells to states and jurisdictions where the substance is currently lawful. The brand is called “Willie’s Reserve” and offers a wide range of products. Considering his history as an enthusiast, this venture should really come as no surprise to most...

Willie Nelson FactsShutterstock

42. He’s Also A Movie Star

In addition to his storied musical career, Willie Nelson has quietly racked up quite the resume as an actor. He has appeared in more than 30 movies over the years—more than even many full-time actors end up making! Maybe he should receive a star on the Hollywood Walk of Fame one of these days!

Willie Nelson FactsShutterstock

43. He Saved The Day

Nelson once broke up a gun fight outside of one of his shows. Members of his stage crew had been battling one another. When things turned violent, the singer put an immediate end to it. He walked off a bus brandishing a bunch of weapons around his waist and calmly asked the group, “What’s the trouble?” That was all it took to prevent what could otherwise have turned into a very ugly scene.

Willie Nelson FactsShutterstock

44. He Got A Famous Actor Out Of Trouble

During a stint in New Mexico, Nelson befriended actor Dennis Hopper. The pair got up to all kinds of shenanigans. But on one occasion, Hopper took things too far. He got extremely intoxicated on a bunch of illicit substances. Law enforcement wound up detaining him. Luckily, he had a true friend in Nelson. The singer went out of his way to bail him out.

Dennis Hopper FactsWikimedia Commons

45. He Owns A Town

There are legends, and then there are legends who have their own entire towns. Willie Nelson falls into the latter category. Filmmakers created the town of Luck, Texas as a set for one of Nelson’s films back in the day, and he liked it so much that he has kept it intact and maintained it as his own ever since. A nasty storm hit the site in 2014, but the singer had it properly rebuilt.

Willie Nelson FactsShutterstock

46. His Song Set An All-Time Record

In addition to his many other impressive accomplishments, Nelson’s song “Crazy” boasts a uniquely legendary achievement. Patsy Cline’s version of it is the most commonly-played jukebox tune of all time. Not too shabby for a guy who spent many years wondering if he could ever make it in the music business!

Willie Nelson FactsNeedpix

47. His Second Marriage Failed

When Nelson’s first marriage ended, he moved on and married his second wife, the singer Shirley Collie. Sadly, this marriage also came crashing down. Things between the couple were fine until one fateful day when an unexpected letter arrived at Nelson's house and gave away a secret of his. And that secret was a big one...

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48. He Lived A Double Life

The letter that arrived turned out to be a bill from a hospital’s maternity ward. Collie wondered why a maternity ward would have fees to be charging to her husband. Well, it turned out that Nelson had cheated on his wife and fathered a child outside of wedlock. Once the secret was out, Nelson divorced his second wife and married the mother of his new child.

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49. He Has Flirted With A Controversial Conspiracy Theory

Nelson’s political activism has caused some serious drama over the years. In one bizarre instance, he told interviewer Larry King that he doubted the US government’s official account of the September 11 attacks. He said that he believed conspiracy theories about the Twin Towers having imploded, insisting that planes could not have caused that kind of damage.

Thought Were Lies But True FactsMax Pixel

50. He Earned The Nickname “Shotgun Willie”

When Nelson learned that his son-in-law, Steve, had been abusing his daughter, Lana, the singer took immediate action. He marched over there and slapped the guy around, promising to come back and drown him if he ever laid a hand on Lana again. When Steve followed Nelson home and tried to shoot at him after the incident, the singer fired back and Steve retreated.

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Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19

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