Everything You Need To Know About Country Music Legend Willie Nelson

Music is a dynamic industry that changes over the decades and even over the years. Musicians are revered as talented individuals who can make art that moves us all, and they gain celebrity status and influence according to their talent and impact on the industry. But not all of them last the ages - many are names that fade into the years as time goes by and leaves them behind when new music trends take over the radio waves. It is a lucky and unique artist who is able to withstand the test of the ages and remain known and loved throughout generations. And one such artist, complete with a complicated life and career, is Willie Nelson. 

Way Back When

Willie Nelson was born back in 1933. In 1933, Franklin Roosevelt was president, the Golden Gate Bridge was in the process of being built, The Lone Ranger radio program debuted, and the Great Depression was looming.

This is the world Willie Nelson was born into, in a town in Texas. Willie can trace his American roots all the way back to the first war - the Revolutionary war.

Left on His Own

From the get-go, Willie’s life was complicated. Willie’s mother left soon after he was born, and his mechanic father got remarried and then moved away as well, abandoning his son and daughter. It was probably devastating for Willie, a real blow to know that his mother and his father both didn’t want anything to do with him.

A child should be surrounded by love in their first years of life, but instead, Willie was left alone. Willie and his sister, whose name was Bobbie, were left to be raised by their grandparents from Arkansas. It’s a good thing for the world that they were!

In the Family

Willie’s grandparents were musically inclined, teaching music in their town, and they were the ones who first introduced Willie to the magic of music. Willie’s grandfather bought him his first guitar when he was six, and taught him the basic chords.

Willie grew up singing gospel in the local church choir alongside his sister, and wrote a few songs before he ever hit double digits in age! It wasn’t an easy life though - during the summer the residents of their Texan town would all pick cotton together, and it was backbreaking work.

Bigger Dreams

Willie Nelson didn’t like picking cotton - he much preferred to sing. So he instead began to earn his wage by singing in dancing halls and barns, parties and wherever would have him.

He had a charm that got him jobs, and he was a very talented guitar player. Even when he was younger, Willie had a voice that people loved to listen to. He began this career at the young age of thirteen and kept on going all through high school. 

Friday Night Lights

Still, he managed to find time to be on the football team, the basketball team, and the baseball team! He really was the typical all American boy, a sportsman and a hard worker both. Plus he worked as a farmer, raising pigs in the dirt.

Willie worked all sorts of odd jobs, from phone operator to tree trimmer to an electrician. He even worked in customer service at a pawnshop - one of the hardest jobs is to work customer service, but Willie did it all!

Yes Sir!

After high school, Willie joined the United States Air Force. He only served for eight months before he came back to America in 1952, where he did one of the most joyous things a man can do when he comes home from war: he got married! Willie married Martha Matthews, but it turns out the marriage would not be as happy a marriage one dreams about. But more on that later, because at first, the fifties were years for Willie to go try and get an education.

He studied agriculture at Baylor University and was even a part of a fraternity, although that was probably a different type of frat life than we see now in our movies! Willie had a bunch of different jobs throughout his time in college, still trying to find himself. Eventually, he joined Johnny Bush’s band as a guitarist.

Rocky Start

This is where Willie Nelson’s career really, truly began. He moved his family to a different town within Texas and became a DJ, where he made his first recordings. It was 1955, and his first songs did not do well, rejected by a record company. His relationship with Martha wasn't an easy one, and they struggled to see eye-to-eye with one another. 

It isn't an ideal situation for anyone to be faced with. But thankfully, Willie had music to pour his heart into and it provided him an escape from his home life. Soon, the tide would change and his music career would finally get the acknowledgment it deserved. 

Trying Hard

Willie went all around America - from Portland to Vancouver to Springfield - trying to find a break for his music. He wasn’t really getting anywhere, just playing in bars, failing to produce a hit record, and losing hope. His first son was born in 1958, and he moved back to Texas, where he got his first break from Larry Butler.

 He wrote a few more songs and sold them for a few hundred dollars, but still, he couldn’t find a break. It was very depressing and discouraging, but Willie’s heart was big, and he was sure of what he was meant to be doing.

Always a Smile on

Willie slowly made his way to Nashville when his second child was born, trying to find a label to sign him. He wasn’t successful until Hank Cochran - a songwriter who worked for Pamper Music - heard him playing during a jam session. Cochran convinced his bosses to give Nelson a break and a contract.

Willie was such a friendly person, with kind words and open arms, that it was hard to say no to him. Willie went on to write many hits for other artists but still had yet to release a song on his own that would get his voice onto the radio. For now, it was just his words. 

Two Is Best

Until that, all changed in 1961, when he was finally recording and releasing his own work. While his third child was born and his marriage was still a disaster, his music career was just beginning. He recorded “Willingly” with Shirley Collie, and it topped the charts at number ten. His second song, “Touch Me” would go on to be number seven on the charts as well.

A year later, he released an entire album! After all the time going from place to place and job to job, he was finally making his dreams come true with “...And Then I Wrote.” What a fitting title for an album about a man who wrote so many songs but only began to sing them almost thirty years after he first put pen to paper.

Golden Man

When you're such a prolific person, it's no wonder that you're worth your weight in gold. Willie Nelson's work throughout the years has proved to be very fruitful, and his net worth is estimated at a whopping $25 Million, the result of decades upon decades of his work in the industry.

Although he did have a set of financial issues, including several bad investments he made in the 80s, he always managed to pay back his debt with his music. What a guy.

Saying Goodbye

In the time that his music career was beginning, Willie Nelson’s first marriage was ending. But all was not lost in the realm of love, for Willie Nelson married Shirley Collie only a little later.

Shirley Collie, the very woman he sang a duet with on one of his first-ever successful songs! They moved to a ranch in Tennessee, where he kept writing and trying to make new music. Not just trying - but succeeding. Willie Nelson has a very particular sound, one that was soon to take America by storm. 

Something Truly Special 

Willie’s music is a beautiful blend of country, jazz, blues, and rock. He has a steady yet nasally voice with a beautiful way of holding onto the words he is singing. His very voice sounds friendly like he’s sitting with you by a campfire while he sings. This is the voice that earned him entry into the Grand Ole Opry in 1965 - the voice, and the guitar.

Willie is an amazing guitar player, he plays bass as well, and overall music flows out of him like a steady stream. From 1966 to 1969 he had many singles reaching the top 25 on the country hit lists, and he had many songs written and performed by other artists. However, his career still hadn’t taken off entirely. 

Had to Take a Step Back

Indeed, it was not just his career that was flat. As his marriage with Shirley began to deteriorate, it seemed like his music career was following suit. Every artist has there ups and downs, as the market can change as the original audience grows older and their tastes develop.

It was clear that Willie didn't have much luck in his marriages, and his career in the music field was not looking too hot either. It seemed that no matter what, Willie was destined to keep taking steps backward, even as it felt he had gone forward. In fact, he became so frustrated by all these turns of events that he quit music yet again. 

Peace and Love

Willie moved back to Texas, hoping to escape the music industry. He became entrenched at the beginning of the hippie movement, enchanted by their philosophy of free love and peace. Willie himself had always been a kind man who wanted to do right by other people. The music of the hippie scene was also incredibly interesting to Willie, and it rekindled his love of the craft.

All this time he had been trying to become successful, and he had forgotten why he loved music in the first place. Music is a way to connect, to send messages, and to bring people together. So he decided to give it one more try.

Shotgun Rider

This is what led to the famous album, Shotgun Willie. It came out in 1973, and while it did not sell well at first it has since become very very well known. It marked a change in Nelson’s style, his overall outlook on life.

Indeed, afterward, he released another album based on his experiences in his marriage, a new and interesting take on the way that music could be used to tell a story. His work was beginning to receive much praise and critical success, as well as the commercial success he truly deserved. In 1974, he was given free rein to make an album entirely as he saw fit.

Freedom to Feel

Thus, “Red Headed Stranger” was born. The album had Nelson’s first number one hit, his cover of “Blue Eyes Crying in the Rain.” Audiences could feel Willie’s pain through his voice, and understand his heart through his music.

Ultimately, they could also feel the hope that was the undercurrent of all of his songs and of his entire life, the determination that he carried and helped him to never give up on his dream.

Family Found Again

He also found a new dream of love, marrying the woman he had cheated on Shirley with - Connie Koepke. Together they had two daughters, and she was by Willie’s side as his star began to rise. Willie helped to give birth to a genre usually known as “outlaw country” which is a type of music that does not abide by what was typical to the genre in the day.

In fact, his first platinum album had the word “outlaw” in the title, further cementing Willie’s constant life living on the edge, away from the typical path of life and what is expected of him. A platinum album is a very rare thing, but Willie achieved this due to his skill and perseverance.

Taking Big Risks

Nelson also had a very unique music portfolio that he released outside of his genre. He had a gospel album that came out in 1976, called “Troublemaker” and this would eventually become a gold album twenty years later. This means that it sold so well, even over all the years that passed, that it earned golden status. 

In the meantime, Nelson went through drama with his managers and producers, eventually switching the person who represented him. He also released his twenty-second album, “Stardust,” which received very critical reviews. There were those who said it would ruin his career!

Becoming a Star(dust)

But in fact, “Stardust” went platinum the very year that it was released. Willie Nelson really was on top of the world, topping the charts all throughout the late 70s.

 He had songs like “If You’ve Got the Money I’ve Got the Time”, “Uncloudy Day,” and “Good Hearted Woman,” all of which hit chords within his audiences and made people related to him, no matter their age or where they came from. But truly, his best was yet to come. And it would come, in the 1980s.

Coming Up Willie

“On the Road Again,” one of Willie Nelson’s most famous and well-known songs, came out in 1980. It’s a song with a plucky guitar, lyrics that speak of friendship and winding roads of destiny, and Nelson’s classic croon. It was followed by “To All the Girls I’ve Loved Before”, another classic. It really seemed like Willie was on top of his game, and this was proven even more so when he recorded “Always on My Mind,” the song that won three awards during the 25th Grammys.

It won Song of the Year, Best Country Song, and Best Male Country Vocal Performance. Willie truly deserved those awards, especially because his strong voice carried such emotion and tenderness throughout the ballad. His version of the song even made it into the Grammy Hall of Fame, a prestigious place many many songwriters and singers never ever see. 

Highway Men to Hell

Then, in the middle of the 1980s, Willie decided to do something different. He formed The Highwaymen along with Johnny Cash, Kristofferson, and Jennings. They became a world-famous band that sold millions and millions of records, toured the world, and were greeted by screaming fans everywhere they went.

To think that Willie had gone from accepting ten dollars for a song he wrote to being a worldwide sensation recording with Johnny Cash and selling out stadiums is incredible! He even released another solo album with recordings of duets featuring Ray Charles and Neil Young, household names in genres of music as well.

Dear Mr. President 

Then, Willie, who had once hitchhiked to Oregon and had to work selling bibles, found himself performing on the lawn of the White House! He had an audience of the President and the First Lady of the United States!

It must have been an incredible and surreal experience for someone who came from nothing to go to the White House. Especially since Willie became a frequent guest of the White House. But even as he was on top of the world, Willie Nelson ran into trouble with the government, or more specifically the IRS. 

Running From the Law

Willie had all of his assets seized when the IRS claimed he owed them thirty-two million dollars. Thirty-two million dollars! That’s so much money that most people never even dream about, but the IRS claimed that Willie had not paid proper taxes on his sudden influx of income.

Willie’s lawyers eventually sorted it out, and his friends that he made throughout his career stuck by him during the trying time, but it must have been a huge shock and horror to have to go through, having all of his hard-earned things taken away from him. 

Three Out of Three Ain't Bad

In 1988 Willie was separated from Connie Kopeke, and for the next eleven years, he would not remarry. Perhaps he wanted a break after having three different marriages, all so close to one another. Instead, he focused on touring, recording new albums, and performing with legendary acts like Phish.

He did eventually remarry, in 1991 to Annie D’Angelo. He and Annie had two kids together, and they are still married, so this time Willie must have gotten something right if it’s lasted nearly thirty years! They met while Willie started his film career in “Stagecoach” - Annie was a makeup artist on set. 

A Deserving Legend

At that point in the 1990s, Willie was a household name and an incredible established artist in the country music, rock, and even jazz scenes. He had proven himself to be a genius of his craft and someone who could always be counted on for a good performance and a good time.

More than that, he had a great smile, he was always welcoming and encouraging to those around him. People remember him as being a very kind man, and indeed he began to champion many causes with his celebrity.

Willie's On The Road Again!

In mid-2024, After weeks of concern over his health, Nelson returned triumphantly at his annual "4th of July Picnic" event in New Jersey. At 91, Nelson had been advised by his doctors to rest after feeling unwell a couple of weeks earlier, but he was soon ready to hit the stage again.

The show featured performances by Mavis Staples, Maren Morris, Bob Dylan, and more. Nelson expressed his excitement, saying, "This year's Outlaw Music Festival Tour promises to be the biggest and best yet with this lineup of legendary artists. I am thrilled to get back on the road again with my family and friends, playing the music we love for the fans we love."

Helping Those He Can

Willie advocated for LGBT rights, for the equality of genders and races. He lent his voice to those who had no voice, like animals. He made an effort to show the terrible lives animals have when they are raised merely for slaughter, and he runs a campaign dedicated to helping horses live a peaceful life without having to worry about being put down.

He has rescued dozens and dozens of horses which he lets roam around on his ranches. He also gives aid to the farmers of America, advocating for small family farming over corporations taking over the industry and pushing the local farmers out of business. Willie has a big heart and gives a lot of charity and time. He even performed at a concert after 9/11, wanting to show support for beautiful America he loves.  

You Can Smoke on That!

Willie is also a very well known advocate for smoking. Now he is on many boards that advocate the legalization of marijuana, and he is a well-known activist for the reform of laws related to the drug. In fact, when marijuana began to become legal in many American states, Willie Nelson opened his own marijuana brand! It’s called Willie’s Reserve, and his wife Annie also plans to create edible marijuana pieces to be sold as well. They believe in the healing power of the drug as well as its ability to open the mind, the heart, and the senses.

He enjoys it so much that in 1970, his cabin famously caught fire while Nelson wasn't home. When he returned and saw it ablaze, he ran into the burning structure to rescue his beloved guitar "Trigger" and a "pound of weed." After the incident, he earned the infamous nickname, "Shotgun Willie," which also inspired the song. 

Renaissance Man

Nelson has many passions outside of music. He loves to golf and always has. He’s a very good golfer due to all the practice that he’s gotten. Beyond golf, he has also appeared in many movies. In more modern films he mostly plays himself; he has voiced himself on an episode of The Simpsons, played himself in Austin Powers and The Dukes of Hazzard sequels, and was even in Zoolander 2.

But he also has acting credits where he played other characters, notably in The Electric Horseman, Stagecoach, and Pair of Aces. Willie reportedly loves to act, and although he has no formal training he’s quite good at it! He has learned from many people he has acted alongside and he also loves to watch action movies, so this has influenced him greatly.

Don't Mess With Willie

In addition to acting and golf, Willie has a very surprising hobby. Due to the comic books on Superman and Batman, Willie had an interest in martial arts as a child, and he pursued that interest through adulthood with much the style that he pursued music. In the early 1980s, Willie began official training in taekwondo, and he eventually earned a black belt!

In the 1990s he began to practice a Korean martial art that he also earned a black belt in, and after twenty years in the discipline, in 2014, he received a fifth-level blackbelt. At the time, Willie was in his seventies. This proves that he is in simply amazing shape for someone of his age and that dedication to a craft and determination, no matter your age or original skillset or even origins, will allow you to master anything at all.

The Nelson Bunch

Altogether, Willie has seven children, three from his first marriage, two from his second, and two from his fourth. Sadly, Willie’s second-oldest son, Billy Nelson killed himself in 1991 by hanging himself with a cord in his home, authorities said. He was 33. It is a terrible thing to lose a loved one to suicide, and Willie, who has such a big and far-reaching heart, took it very hard.

  

It must be hard to raise so many kids, especially when you are trying to establish yourself and your career, and when the marriages that you have had with their mothers are tumultuous at times. But Willie’s children generally seem to like him, and many of them have even gone into the music industry themselves. Willie doesn’t just inspire strangers, but his own children as well. 

Smoke in the Lungs

However, now Willie gets to spend time with his family on his tour bus, or on his ranches in the Southern United States. He has a home in Hawaii, where he goes swimming often and hang out with his celebrity neighbors. Unfortunately, when he was in paradise-like Hawaii over thirty years ago, a terrible thing happened to Willie.

While swimming in his pool, one of his lungs collapsed! This was due to the years of smoking cigarettes and marijuana that Willie had done. He had to immediately quit tobacco, and find a way to smoke marijuana that was not so harmful to his health with so much smoke. Of course, for the sake of his family, he has done so, and he has also taken other health precautions like caring for his hands when they go through carpal tunnel pains. 

What You Have Taught Us

While once upon a time Willie could claim his influences were the likes of Hank Williams, Frank Sinatra, Ray Price, Louis Armstrong, Django Reinhardt, and Bob Wills, now Willie Nelson serves as an influencer himself on millions of fans. It isn’t just his unique style or life story that people find inspiring, however.

Wilie’s attitude of free love, letting people live as they are, trying to understand each other, and always working on yourself and moving forward is incredibly inspiring. Willie performs with up and coming country artists often and gives them encouragement and inspiration. He knows that he has left a long-lasting mark on the music industry, and no one takes him for granted.

Recognized 

Of course, Willie is recognized by all as the icon he is. He is in the Country Music Hall of Fame as of 1993, has often been included in Rolling Stones lists of top 100 Greatest Singers and top 100 Greatest Artists, has a Country Music Award Lifetime Achievement Award named after him (of which he was the first recipient) and he has many other awards.

He also has been recognized for his charity, especially his charity in Farm Aid to help local farmers. He is known for his fun-loving, free spirit and the red hair that is now gray. 

Lessons Learned the Hard Way

It is not only good times that Willie brings, but love, memories, and peace. He has finally found his calling after so many years of struggling to make it, and he finally found his love after so many years of trying and failing to find the right match. If we can learn anything from Willie Nelson is to never give up on our dreams.

We are never too old to achieve them, never too old to keep trying, and never too late to succeed. And of course, as we keep chasing our stars we should keep a smile on our face, a joke in our pocket, and a bit of smoke if that’s your kind of vibe. Don’t worry: Willie Nelson will never judge you! All he wants is for everyone to have a good time.