The Wild Ride Of Willie Nelson’s Life

Depending on who you ask, Willie Nelson is either considered a country music trailblazer, America’s favorite stoner and marijuana advocate, or as Nelson himself would put it, “a hillbilly from Hill County, Texas.” Whether or not some or all of these are true, one thing is for sure: Willie Nelson is an American icon. From the humblest beginnings to fame that didn’t seem to get to his head, here’s a look at Willie’s wild life.

Born At The Height Of The Great Depression

Born At The Height Of The Great Depression

Willie Hughes Nelson was born in a small Texas town on April 29, 1933, at the height of the Great Depression. Like many parents at the time, Nelson’s left him and his older sister Bobbie behind, leaving them in the care of their grandparents. Of his upbringing, Nelson writes in his memoir, My Life: It’s A Long Story, “Might sound corny, but the truth is we were dirt poor in material possessions, but we were rich in love.” Nelson’s grandfather was a blacksmith who bought six-year-old Nelson his first guitar. Under their grandparents’ care, Nelson and his sister regularly attended their local Methodist church, where they gained their earliest exposure to music, for which Nelson had a distinct ear. By the age of seven, Nelson had already written his first song.

Nelson’s Grandmother Encouraged His Ear For Music

Nelson’s Grandmother Encouraged His Ear For Music

Willie Nelson told Rolling Stone in 2004 that his first song was actually inspired by his grandmother: “Back when we used to take music lessons from our grandmother… if we’d get the lesson right that day she’d take a gold star – a little star, about the size of your finger, with glue on one side – and she’d stick it on the sheet of music, which meant you’d done well. So I wrote this song with the line ‘They took a gold star away from me when you left me for another, long ago.’ I’d never been left by anybody [at age seven], so it was kind of funny.”

From Cotton Picking To Honky Tonk Singing

From Cotton Picking To Honky Tonk Singing

Growing up in Abbott, Texas, it was normal for children to spend summers and schoolday afternoons picking cotton, which is exactly what Nelson and his sister did for $1.50 a day in the 1940s. In Roll Me Up and Smoke Me When I Die, Nelson recounts, “[There] I was pulling along a sack of cotton—a Cadillac came by with its windows rolled up. There was something about that scene that made me start thinking more about playing the guitar. Here I was picking cotton in the heat and thinking, There’s a better way to make a dollar, and a living, than picking cotton.” To avoid picking cotton so much, Nelson reportedly found other gigs by singing at local honky tonks and dance halls from age 13 throughout the rest of high school.

From Military Man To College Dropout

From Military Man To College Dropout

After finishing high school in 1950, Willie Nelson joined the U.S. Air Force. He only was able to serve for less than a year before he was discharged due to his back problems. but Nelson remains a passionate supporter of veteran’s issues today.

With the military out of the question, Nelson enrolled himself at Baylor University, where he studied agriculture for a couple years before ultimately dropping out. Focusing on his music, Nelson resorted to a string of odd jobs amidst performances with a local band—for which he made as little as 50 cents a night.

Willie Nelson Became A Famous Radio DJ

Willie Nelson Became A Famous Radio DJ

In the late 1950s, Nelson also worked as a disc jockey for local radio stations around Texas. During this time, he used the radio station equipment to make his first two recordings, “The Storm Has Just Begun” and “When I’ve Sung My Last Hillbilly Song.” Nelson eventually made it to the Pacific Northwest, where he lived in Portland, Oregon with his mother. He was soon hired by KVAN in Vancouver, Washington. Nelson hosted a radio show called the “Western Express,” where he introduced himself as a “cotton-pickin’, snuff-dippin’, tobacca-chewin’, stump-jumpin’, gravy-soppin’, coffee-pot-dodgin’, dumplin-eatin’, frog-giggin’, hillbilly from Hill County, Texas.” He made $40 a week for the show and gained a cult following.

A Marriage Like Custer’s Last Stand

A Marriage Like Custer’s Last Stand

Willie Nelson met and married his first wife, Martha Matthews, in 1952. He was 18, and she was 16-years-old. In 1980, Nelson recounted his first marriage to People magazine saying, “She was a full-blooded Cherokee and every night with us was like Custer’s last stand. We’d live in one place a month, then pack up and move when the rent would come due.” Six years into the marriage, he and Matthews had three children to support. To make ends meet, Nelson worked various odd jobs including selling Bibles and vacuums door-to-door, working as a plumber’s helper, and also as a sales manager for Encyclopedia Americana. Still devoted to his music, Nelson worked nights performing in honky tonks.

Willie Let The Liquor Get The Best Of Him

Willie Let The Liquor Get The Best Of Him

Nelson and his family eventually moved to Nashville, Tennessee to help boost his music career, where he wrote and sold songs to other popular musicians at the time. Nelson frequented Tootsie’s Orchid Lounge near the Grand Ole Opry, where other singers and songwriters hung out. His family still struggled financially, leading Nelson to drown his sorrows in drinking, which ultimately lead to the dissolution of his first marriage.

Nelson told People magazine, “I came home drunk and while I was passed out, she sewed me up in a sheet. Must’ve taken her two hours. Then she got a broomstick and started beating the hell out of me. I woke up in this straitjacket, getting pounded like a short-order steak. By the time I got loose, she’d lit out the car with the kids, her clothes, and my clothes. There was no way I could follow her naked, and that was kind of the end of it.”

Nelson First Found Success As A Songwriter

Nelson First Found Success As A Songwriter

Following the end of his first marriage, Nelson was able to write more songs for other artists including Patsy Cline’s “Crazy” which all cracked the country Top 20. Nelson eventually signed with Liberty Records in 1961 and recorded his own music at the Quonset Hut Studio. Nelson’s success might be attributed to the way he smartly avoided Nashville’s formulaic songwriting, telling People magazine, “I’d say that 99 percent of what I write has come from my own experience. A person could probably start from my first song and go all the way to my last and—if he knew what to look for—write my autobiography.”

Nelson’s Next Chapter Was Looking Up…

Nelson’s Next Chapter Was Looking Up…

Willie Nelson’s earliest hit as a contracted singer and songwriter include “Touch Me” and “Willingly,” which he recorded with singer Shirley Collie, who became his second wife. After marrying in Las Vegas in 1963, the couple performed and toured together, with Collie joining Nelson’s band as a bass player. By 1964, Nelson had convinced Collie to settle down and help him raise his kids from his first marriage on a 200-acre ranch he bought in Ridgetop, Tennessee on the outskirts of Nashville. It was also around this time that Nelson transitioned from Monument Records to RCA Victor (as it was known at the time), where he signed a contract for $10,000 a year.

…But It Included A Second Divorce And A New Daughter

…But It Included A Second Divorce And A New Daughter

Willie Nelson, Connie, Paula and Amy Nelson

In 1965, Willie Nelson joined the Grand Ole Opry, where he met fellow country music artist, Waylon Jennings. His continued success, however, only drove him and his wife Shirley to neglect their marriage as they explored their dalliances with drinking, drugs, and infidelity. At this time, Nelson began seeing Connie Koepke while on tour in Texas. By 1971, Shirley filed for divorce after she found a hospital bill from a Houston maternity ward that was charged to Nelson for the birth of a daughter he fathered with Connie Koepke. Nelson and Koepke married that same year and had a second daughter.

Why Willie Nelson Walked Into A Fire

Why Willie Nelson Walked Into A Fire

Shortly after marrying Koepke, Nelson’s career in Nashville was beginning a steady decline as he squandered his money on unprofitable tours. But even worse than his career stalling, was the time that his house in Tennessee burned down. Nelson braved the flames and went into the house to save his beloved guitar, Trigger, and another special possession he would later tell People: “By the time I got there, it was burning real good, but I had this pound of Colombian grass inside. I wasn’t being brave running in there to get my dope—I was trying to keep the firemen from finding it and turning me over to the police.” Nelson managed to save his weed and his guitar, but unfortunately lost 100 tapes of unrecorded songs. He took the house burning down as a sign to relocate.

Austin Gave Nelson His Signature Look

Austin Gave Nelson His Signature Look

Gary Miller/Getty Images

In 1972, Nelson bought himself out of his recording contract with RCA for $14,000 with the intention of retiring. Nelson packed up his family and relocated to Austin, Texas, where the “outlaw country” style that Nelson was known for was a burgeoning trend. Austin’s relaxed atmosphere encouraged Nelson to loosen up and adopt the bandana, braids, and beard look he has rocked ever since. As a result, Nelson was able to revitalize his career and signed with Atlantic Records, becoming the label’s first country music artist for $25,000 a year. After forming his backup band, named The Family, Nelson was back in the spotlight.

He Was Finally Free To Be Himself

He Was Finally Free To Be Himself

By 1975, Nelson had moved to Columbia Records, who gave Nelson complete creative control. The resulting first album with Columbia was Nelson’s Red Headed Stranger, which included “Blue Eyes Crying in the Rain,” a cover of Fred Rose’s 1945 version. Nelson cemented his “outlaw” image with fellow singers Waylon Jennings, Jessi Colter, and Tompall Glaser by creating a compilation album called Wanted! The Outlaws. Nelson subsequently released The Sound in Your Mind and Troublemaker. By 1979, Nelson starred in his first movie, The Electric Horseman. 11 years after its release, Red Headed Stranger was turned into a film, with Willie Nelson in the lead role.

Why Nelson Needed To Quit

Why Nelson Needed To Quit

Given Willie Nelson’s current reputation, it might come as a surprise to some that his original vice in addition to drinking was smoking—cigarettes, that is. Nelson was a frequent smoker since a young age, but by 1981 a collapsed lung forced him to cancel some shows and go to the hospital. That first visit didn’t stop Nelson, however, and eventually, he had to make a choice. In 2012, Nelson told NPR, “I had gotten up to two, maybe three, packs a day. My lungs were bothering me and I’d had pneumonia two or three times. I was also smoking pot, and I decided, well, one of them’s gotta go. So I took a pack of Chesterfields and took all the Chesterfields out, rolled up 20 big fat ones and put [them] in there, and I haven’t smoked a cigarette since then.”

This Outlaw Couldn’t Outrun The Law

This Outlaw Couldn’t Outrun The Law

Willie Nelson is an infamous pot smoker—something he is open and unapologetic about. But despite being a famous country singer, Nelson is not above the law. The first time he was arrested for marijuana possession was in 1974 in Dallas, Texas. 20 years later, he was arrested in Waco, Texas for having one joint on his person. The second arrest caused him to miss the Grammy’s that year since he had to appear in court. In 2006, police apprehended marijuana and hallucinogenic mushrooms from Nelson in Louisiana, for which he served six months of probation. His latest arrest happened in 2010 when six ounces of marijuana was found on his tour bus. Nelson merely paid a fine for his last offense.

The Cops Don’t Even Care Anymore

The Cops Don’t Even Care Anymore

Nelson doesn’t think much of getting arrested for marijuana-related offenses these days, telling Rolling Stone in 2014, “[The cops] mostly want autographs now. They don’t really bother me anymore for the weed because you can bust me now and I’ll pay my fine or go to jail, get out and burn one on the way home. They know they’re not stopping me.” Willie Nelson’s frequent use of marijuana has made him an advocate for its legalization for many years. He currently serves as a co-chair for the National Organization for the Reform of Marijuana Laws (NORML) advisory board.

But They Certainly Cared About His Unpaid Taxes

But They Certainly Cared About His Unpaid Taxes

Nelson’s pot offenses aren’t the only interactions he’s had with the law. In 1990, the IRS showed up to his house and seized all his property and assets in six states, claiming that he had a total tax debt of $32 million. Much of Nelson’s income was also hidden in illegal tax shelters as a result of poor financial advice he received years earlier. Eventually, Nelson reached a settlement with the IRS on which he owed $9 million. Nelson attempted to cover the costs by releasing a two-disc collection of acoustic versions of Nelson’s hits, as well as more intimate songs featuring just Nelson and his guitar. The IRS Tapes: Who’ll Buy My Memories? sold for $19.95, with 15 cents of every dollar of the sales going to the IRS.

The Tools Of The Trade

163716418DM087_Keith_Urban_

Frederick Breedon IV/Getty Images

Although the IRS seized Willie Nelson’s properties and assets—including boxes of master tapes and his gold and platinum records—one thing they didn’t manage to get a hold of was Nelson’s guitar, Trigger. Knowing that the IRS was coming for him, he thought ahead and had his daughter ship his beloved Trigger to Maui for safe keeping. Nelson has been using Trigger since 1969—almost 50 years! He told Uncut in 2014, “I’ve got to take good care of Trigger… He’s had a couple of problems. We’ve had to go in and do some work on the inside, build up the woodwork in there a little bit over the years. But Trigger’s holding up pretty good.”

Where Willie’s At Nowadays

Where Willie’s At Nowadays

For a third and final time, Willie Nelson found himself divorced. But by 1991, he married his fourth (and current) wife, Annie D’Angelo. As of 2017, they have been married for over 20 years, making it Nelson’s longest marriage. Nelson and D’Angelo had two sons, giving Nelson a total of seven kids in his lifetime (three from his first marriage and two from his third). Currently, Nelson, D’Angelo, and their sons live on Maui. Their home is reportedly located in a self-sustaining community in which the homes run entirely on solar power and they allegedly have some pretty famous neighbors: Woody Harrelson, Owen Wilson, and Kris Kristofferson, just to name a few.

Nelson Wants You On The Road Again

Nelson Wants You On The Road Again

The outlaw country singer founded Willie Nelson Biodiesel in 2004, producing Nelson’s own brand of biofuel called BioWillie. As the story goes, Nelson’s wife Annie purchased a diesel-fueled car, which she only filled with biodiesel. The Nelsons were impressed by biodiesel’s efficiency and performance and realized that its use could minimize the U.S.’s dependence on foreign oil and provide work for family farmers that could produce biodiesel, which is made from vegetable and soybean oils. Washington Post quoted Nelson, who said, “There is no need going around starting wars over oil… We have it here at home. We have the necessary product, the farmers can grow it.”

Like Father, Like Daughter: Paula Nelson Arrested For Marijuana On Her Tour Bus

Like Father, Like Daughter: Paula Nelson Arrested For Marijuana On Her Tour Bus

Willie Nelson’s daughter Paula follows in her father’s footsteps in more ways than one. Like her father, Paula is also a musician. The country singer has released five albums and was a radio DJ in Texas. Also like her father, she smokes marijuana. In 2014, on April 20th, a day when stoners are known to celebrate smoking marijuana, the tour bus Paula was on was pulled over by police in Menard, Texas for speeding. Once they found out Willie Nelson’s daughter was on board, they searched the bus for drugs and found the marijuana. Following her arrest, she told her fans, “Speak up on ‘Legalizing’ where it counts the most in your state.”