Secrets Of Willie Nelson’s Crazy Life


Willie Nelson is one of country music’s greatest icons, with a career spanning over 5 decades. At 84 years old, it’s no wonder his legendary career has spawned many secrets.

Shotgun Willie

Nelson’s famous nickname was earned after he heard that his daughter was being abused by her husband, Nelson threatened him. No sooner did he arrive back at his house, his son-in-law drove up and start shooting at the house, to which Nelson returned fire. Nelson then set a trap and shot out the tire on his son-in-law’s car.

Willie Nelson

Wiley Willie

Ever the outlaw, Nelson claims to have snuck up to the roof of the White House for a smoke. An outspoken advocate for recreational activities, the incident supposedly took place shortly after Nelson’s release from a Bahamas prison after incriminating materials were found in the pocket of his jeans. The incident was not his first or his last possession-related arrest. Though Nelson has played coy with the details over the years, according to a recent interview his companion on the roof was none other than Chip Carter.

willie and chip

Bedroom Black Belt

In the early 1990’s, a woman filed a $50 million lawsuit against Nelson claiming that he promised to marry her after a 9 hour bedroom marathon, complete with a tandem acrobatic somersault. Though Nelson has never come out and denied the incident, and has even been quoted as saying that it was the only true story written about him. He reneged on that statement after the fact, saying if it were true he should have at least remembered the first 4 or 5 hours.

nelson black belt

Superstar Slur

It was revealed in the 2008 biography about Nelson that he used to call Charley Pride, one of only three black singers to be inducted into the Grand Ole Opry, “Supern****r.” When pressed about using the racial slur, Nelson claimed he used it facetiously in order to reduce the power of the word as used by actual racists. Nelson has been well known as an advocate for social justice, and would embrace Pride afterwards as a public display of their deep friendship.

Willie Nelson Charley Pride

Birmingham Brawl

In the late 70’s, Nelson once again found himself in the midst of a firestorm, after he finished playing a show in Birmingham, Alabama only find himself caught in the crossfire of a gun battle taking place in the parking garage. Chaos ensued as the audience exited the arena, and police couldn’t figure out where the shots were coming from. Willie disappeared into his bus before returning with two revolvers stuck into his belt, and ending the ordeal.

Willie Nelson Cowboy

Blindsided in Chess

In 1984, Nelson released a hit duet with Ray Charles, “Seven Spanish Angels”, a collaboration which gave rise to several amusing stories, including the time Charles challenged Nelson to a blind chess match. While Nelson was visiting Charles in his Austin hotel room, the latter challenged him to a round of chess, but insisted on keeping the lights off in the room. Nelson recalls that the pieces were all the same color and imprinted with braille. Unsurprisingly, Nelson lost 3 rounds in a row.

willie nelson ray charles

Sleeping Prodigy

Willie Nelson might be known for his extensive discography, but he is such a musical genius that his current wife, Annie D’Angelo reports that rather than sleep walk, she’ll see him playing “sleep guitar.” She explains how he’ll sleep lying on his back, all the while miming the motions of holding and playing a guitar, scoring a soundtrack to his dreams. How much of his sleep songs he remembers himself is still up for debate, as D’Angelo had to spark the recollection.


Early Failures

Nelson recorded his first songs in 1955 while working as a disc jockey in Pleasonton, Texas for KBOP radio, where he was hired despite never working in radio before. He used old tapes in the studio to lay down the tracks for “The Storm Has Just Begun” and “When I’ve Sung My Last Hillbilly Song”, which he then sent to SARG Records, a local label. Both demos were rejected by the label, though “The Storm Has Just Begun” was later released as a B-side in 1959.

Young Willie Nelson singing

Camping Out

Though Nelson started out by taking advantage of the creature comforts afforded to stars in the music world, he soon realized he much preferred to sleep on his tour bus than in a hotel, even when the bus was parked just out front. Even while the rest of his crew would sleep inside, Willie would remain on the bus alone. He says he’s spent roughly 6 months a year sleeping on his bus for the last 30-40 years. With a fridge, tv, computer, and radio on board, life on the bus is far from rough.

willie nelson tour bus

Grandparents Legacy

Nelson’s parents left him and his sister Bobbie to be raised by their paternal grandparents when they were very young. Luckily for Nelson’s career, his grandparents had been music teachers and introduced the children to music at a young age. Grandpa William, a blacksmith by trade, bought young Willie his first guitar at 6 years old. Nelson and his sister also sang in the gospel choir at their local church. The encouragement his grandparents gave him was an invaluable start to his prolific career.

Willie Nelson grandma

Ditched on the Road

During a jobless period early in his career, Nelson decided to seek out his absent mother in Portland, Oregon. In order to get there, he needed to hitchhike from San Diego. Unfortunately for Nelson, no one picked him up, and he was stuck sleeping in a ditch. He eventually was able to board a freight train at a rail yard that took him as far as Eugene, where he borrowed money in order to catch a bus to take him the rest of the way.

nelson oregon

Early Retirement

In 1972, Nelson decided to quit the music industry. He had suffered a series of unsuccessful tours that ate up all of his music royalties and was in the midst of divorcing his second wife, Shirley Collie. His professional failures coupled with personal turmoil led him to buy out the remainder of his contract for $14,000. He subsequently moved to Austin, where the budding hippie music scene inspired him to come out of retirement. The whole stint lasted less than a year.


Farm to Study Hall

Inspired by his rural upbringing, Nelson enrolled in Baylor University to study agriculture from 1954 to 1956. He grew up picking cotton with his grandparents, though he reportedly hated it, and turned to music to earn money, even at a young age. He later raised pigs for the Future Farmers of America during his high school years. Like his early cotton picking days, studying agriculture did not last long, as he dropped out after only two years in order to again pursue a career in music.

willie nelson dukes of hazzard

Going Greek

During his stint at university, Nelson joined the fraternity Tau Kappa Epsilon. Nelson is not the only famous Tau Kappa Epsilon alumn, better known by the brothers as ‘Tekes,’ as President Ronald Reagan also joined their ranks during his college years. The 40th president remained an active member of their alumni corps, even hosting events at the White House during his time in office. The same cannot be said for Nelson who said goodbye to Greek life when he dropped out of college.


Red Beginnings

Willie Nelson’s first ever public performance took place at his church when he was 6 years old. He recited a poem, as his first song had not yet been written, but he was so nervous about his performance that he compulsively picked at his nose until it began to bleed, which ruined his white suit. The incident earned him the childhood nickname “Booger Red,” though this was just the first of many different nicknames he would eventually earn throughout his life.

Willie Nelson

Bohemian Baby

The first band Willie Nelson ever joined was a Bohemian (aka Czech) polka band in Abbott, Texas, called ‘The Rejcek Family Polka Band.’ He joined at 9 years old, eventually becoming both their lead singer and guitar player. He recalls having almost no equipment when he began playing with them, and could play as loud as he wanted, since the audience could scarcely hear him anyway. During his high school years, he was able to tour the local area with the band.


Country Outlaw

In the mid-1970’s, Nelson developed a new style of country music along with Waylon Jennings, that they coined ‘Outlaw Country.’ They decided to go with the moniker of ‘Outlaw” because their new style of country did not adhere to the conservative standards of Nashville country at that time. Their album “Wanted! The Outlaws” was released in 1976, also featuring Jessi Colter and Tompall Glaser. It was the first country music album to go platinum, which cemented the pair’s outlaw image.

willie nelson wanted outlaws

Will of All Trades

Wille Nelson has held an incredible variety of jobs throughout his life. Though he started as a humble cotton picker, he also worked as a relief phone operator, tree trimmer, and pawn shop employee. Later on, he worked as a disc jockey for local radio stations, as a night club bouncer,  a dishwasher, and as a saddle maker. During one of his brief stints away from the music industry, he also picked up work as a door to door bible and vacuum salesman.


Environmental Activist

A man with rural beginnings, Wille Nelson has never been shy about his connection to the land. He has lent his voice to many charity projects over the years, but has always been quite vocal about environmental issues. Most recently, he wrote a book hailing the benefits of using diesel bio-fuels, which are produced from vegetable oils like corn and soy. He and his wife Annie became partners in building a bio-diesel plant in 2004, before going on to form Willie Nelson Biodiesel (‘Bio-Willie’) in 2005.

willie nelson biodiesel

Child Star

The first song Willie Nelson ever wrote was inspired by the gold stars his grandmother gave him and his sister for completing their music lessons properly. He recalls that she would take the little sticker, and adhere it to the sheet of music they’d been working on. The lyrics to the song went, “They took a gold star away from me when you left me for another, long ago.” He was only 7 years old, and didn’t know anything about that sort of heartbreak.

willie nelson and sister bobbie

Band Of Carters

Nelson was a frequent guest at the White House during the Carter years, as the former President was and still is a huge fan.  During a 1980 performance on the South Lawn, he performed a duet with then First Lady Rosalynn Carter . The song? “Up Against the Wall, Redneck Mother.” President Carter and his wife continue to join Nelson onstage when they come to his concerts, and most recently sang “Amazing Grace” with him in at an Atlanta, Georgia show in 2016.

willie nelson - rosalynn carter

Letterman Nelson

As a student at Abbott High School in the 1940s, he played on a number of sports teams. He was a halfback on the football team, a guard on the basketball team, as well as playing shortstop for the high school baseball team. All the while he was touring locally as a singer and guitarist with The Texans, a band started by his sister’s husband, Budd Fletcher. According to Nelson, he was never the greatest athlete, but as always enjoyed being active, and continues to engage in physical activity even today.


Smoke Screen

A number of years ago, while both were in Amsterdam, Snoop Dogg and Willie Nelson agreed to a smoke off. Snoop Dogg, thinking he had the challenge in the bag showed up under-prepared for the sheer arsenal of the Willie Nelson stash, who brought along various tools of the trade. He says to this day, Nelson is the only one who can beat him, and that he crawled away from their Dutch challenge while Nelson was still going strong.

willie nelson snoop dogg

Willie on the Wing

In 1950, Willie Nelson joined the Air Force, just as the Korean War was beginning with the intention of becoming a jet pilot. He completed his basic training at Lackland Air Base in San Antonio, Texas. In Nelson’s words, he was too “absent-minded” to become a pilot, and eventually received training as a medic. Despite his athletic past, Nelson only served for about 9 months before being medically discharged due to back problems sustained through farming in his youth.

air force willie

Farmer Nelson

Though his days bailing hay and farming pigs are long behind him, Willie Nelson is still a passionate advocate for small farms. In 1985 he set up Farm Aid along with Neil Young and John Mellencamp to raise awareness about the importance of small, family farms. The organization began as a benefit concert in Chicago, and featured Nelson along with Bob Dylan, Billy Joel, and other well-known musicians. The organization has grown since then, with Nelson serving as president of the board.

farm aid

Tax Trouble

Due to severe mismanagement of his money, including tax evasion by one of his managers, the IRS seized $32,000 in assets from Nelson in 1990. Many of his friends purchased his belongings at auction, and then leased them back to Nelson for a nominal fee. In order to pay the rest, he released “The IRS Tapes: Who Will Buy My Memories?” as a double sided album, with all proceeds going towards his debt. He was able to clear it entirely by 1993.

Willie Nelson IRS tapes

Surviving the Fall

Nelson’s friend, Larry Trader has talked about the time Nelson survived a small plane crash near the Western town where the Alamo was filmed. Happy Shahan was reportedly watching the plane come in, knowing Nelson was on board, when the plane flipped while landing on the runway. Ever the publicity man, Shahan called the local press, before he saw Nelson and the pilot limp up his driveway together, a little scratched up, but otherwise intact.

Willie Nelson Waylon Jennings

The Braidy Bunches

When Willie Nelson was first starting out, he kept his image clean cut and was clean shaven, like many others in the early 1950s. He first grew his hair out starting in the early 70s, which led to him braiding his hair in order to keep it out of the way during his shows. Sometime in the 80s, he cut them off and gave them to his manager. They ended up in the hands of his friend Waylon Jennings, who later auctioned them off for a whopping $37,000.

Willie Nelson braids

Chart Topping Legacy

Nelson’s 1978 Stardust, an album of pop standards, was such a hit that it remained on the country charts for 540 consecutive weeks. That translates to a full ten years on the charts. Critics predicted that the album would ruin his career, but Nelson proved them all wrong when it went platinum later that year. Stardust became a critical and commercial success, and by 2002 it had gone quintuple platinum, and was inducted into the Grammy Hall of Fame for the class of 2015.

Willie Nelson Stardust

From Country to TV Star

During Nelson’s 1975 tour, following his newfound creative successes, he raised money for PBS-affiliated stations throughout the country to promote their new concert series, “Austin City Limits.” The pilot episode was released later that year starring Nelson, which expanded into a 10 episode season in 1976. The show was responsible for giving Austin the moniker of “Live Music Capital of the World” and has been running now for over 40 years. The program also inspired the creation of the Austin City Limits Music Festival.

Willie Nelson Austin 1974

Out of the Fire

In 1970, Nelson’s Tennessee ranch burned down. It had been a tough year for Nelson, but he was able to run in and save several prized possessions, including two guitar cases, one that housed his trusted guitar, Trigger, and another that served as a conduit for a large amount of his favorite recreational activity. His other possessions weren’t so lucky. The night before the fire, he and Henry Cochran had written 7 new songs together. All in all, he lost over 100 tapes of unrecorded songs.

Willie Nelson trigger

On the Plane Again

“On the Road Again,” Nelson’s hit single from the 1980 movie Honeysuckle Rose, was supposedly written on a paper bag while traveling on an airplane with the film’s producer, Sydney Pollack, who requested that Nelson write about life on the road as for the film’s theme. The song has become one of Nelson’s most recognizable songs, and won him the Grammy Award for Best Song a year later. It was his 9th number 1 single on the Country and Western charts.

Willie Nelson Honeysuckle Rose

Cowboy Electric

Willie Nelson’s first leading role in a film may have been in Honeysuckle Rose, but he made his film debut a year earlier as Wendell Hickson in The Electric Horseman, which starred Robert Redford and Jane Fonda. The film was a “western adventure-romance” about a former rodeo champion who runs away with a famed racehorse, in order to release it to a better life in the wild. According to Sydney Pollack, who directed the film, Nelson improvised almost all of his dialogue.

Willie Nelson Electric Horseman

Any Other Name

Willie Nelson is surprisingly not named for his grandfather William (who was known by his middle name, Alfred), but was given the name Willie by his cousin Mildred. She also chose his middle name ‘Hugh’ in honor of her recently deceased younger brother, Hugh. His parents were Merle and Ira Doyle Nelson, neither of whom were very present in his childhood. His mother left shortly after his birth, and his father left the family after he remarried.

Willie Nelson

A Texan Shakespeare

Nelson may be best known as a prolific songwriter, but he has also written 9 books on a variety of different subjects. His first book, which he co-wrote with Bud Shrake was an autobiography called Willie: An Autobiography. It was released by Simon & Schuster in 1988, and was well-received by critics. He has since penned several other collections of memoirs, a book on his philosophy of life, as well as a book about the benefits of bio-diesel called “On the Clean Road Again”



Jedi Master Nelson

Nelson was introduced to the world of martial arts through comic books in his childhood, which inspired him to order several manuals on jiu-jitsu. He began practicing Tae Kwon Do in the 80s, and would tape himself practicing the moves on his tour bus, in order to send them to his supervising master for critique. After practicing for over 20 years, the Grand Master Sam Um presented him with a 5th degree black belt in a ceremony in Austin.

Willie Nelson Taekwondo

Hawaiian Haven

Nelson’s home is located on the island of Maui, in a community of self-sustaining houses that are populated by other eco-conscious celebrities, including Woody Harrelson and Owen Wilson. The houses there are mostly run off of solar power, in order to lower their carbon footprint. Nelson also owns property in Austin, Texas, where he lived when his music career first took off. In addition to his Austin ranch, he also owns a local church and a grocery store.

Willie Nelson Hawaii


The first mainstream success Nelson had as a musician was a songwriter for other famous artists. While his first few records were commercial failures, he finally gained a foothold with the release of Billy Walker singing “Funny How Time Slips Away,” Roy Orbison’s cover of “Pretty Paper,” and most famously, Patsy Cline’s recording of “Crazy,” which went on to become the biggest jukebox hit of all time. Cline’s husband discovered the song when he met Nelson at Tootsie’s Orchard Bar in Nashville.

Patsy Cline Crazy

A Marrying Man

Willie Nelson has gone through his fair share of marriages. His first marriage to Martha Matthews lasted for 10 years, but was marred by violence and instability. He married Shirley Collie in 1963, but they divorced when she discovered that he had fathered a child with Connie Koepke, whom he married later that year. The couple split in 1988, after 17 years of marriage, but Nelson pressed on and married 4th and current wife, Annie D’Angelo in 1991.

Willie Nelson Fans

Willie’s Reserve

Nelson is taking his agricultural background to new heights with his current business venture, Willie’s Reserve. He plans on releasing his own varietals of high-quality, medicinal herbs, as well as equipment for their consumption, now that several states have legalized their sale and purchase. According to a recent interview, the idea hedges him on making a name for himself in the budding industry in the same way that Paul Newman made a name for himself as a purveyor of natural food products.

Willie's Reserve

High Achiever

In 1993, Nelson was inducted into the Country Music Hall of Fame, and was chosen as the recipient of the Kennedy Center Honors in 1998. In addition to the recognition of his musical contributions, he has also been inducted in the Agricultural Hall of Fame, has won the Gershwin Prize, awarded by the Library of Congress, received the ‘Feed the Peace’ award from the Nobelity Project for his work with Farm Aid, and received an honorary doctorate from Berklee College of Music in 2013.

Willie Nelson Country Music Hall of Fame

The Legend Continues

Even at 84 years old, Nelson is still writing and recording music. His 2014 album, Band of Brothers, was the first album to top the country charts since “The Promiseland” in 1986, and reached number 5 on the Billboard 200, the highest position he reached on the chart since 1982. Earlier this year, he released “God’s Problem Child,” which he mostly co-wrote with Buddy Cannon. The album opened at number one on the country charts, and even reached number 10 on the Billboard 200.

Willie Nelson problem child

Grand Ole Debut

Before he made his debut at the Grand Ole Opry in 1965, Willie Nelson had mostly played at bars and honky tonks. Because of the vulgar reputations these sorts of venues carried, his daughter Lana recounts that she wasn’t able to see him play until he began performing at the Grand Ole Opry in Nashville. Lana, born in 1953 with his first wife Martha Matthews, was 12 years old before she first saw him perform in public.

willie nelson family

Willie Nelson’s Secret Family

Though Willie Nelson has fathered 7 children among his 4 wives, he also recently discovered he had a secret family with another woman. An old flame of Nelson’s, Mary Haney, gave birth to a daughter, Renee, and never told Willie, as the two had lost touch by then. Renee it turns out, also has a daughter, Noelle, and a granddaughter Jordan. Nelson was happy to learn of hidden family, and only regrets that he didn’t find out about them sooner.

Willie Nelson Children