As one of the greatest icons on the country music scene, Willie Nelson has written and recorded over 60 albums during a career that has spanned over 50 years. In addition to his unrivaled musical legacy, Willie is one of the most well-known advocates for the legalization of marijuana in America. But it seems when it comes to matter of love, this ol’ cowboy has had his fair share of trouble in that department. He’s been declared a serial monogamist, but infidelity always seems to find it’s way into his relationships.
A Legend Is Born
Born in 1933, Willie’s parents separated soon after he arrived in the world, with his mother leaving shortly after he was born. His father also moved away soon afterward, leaving Willie and his sister Bobbie to be raised by their paternal grandparents. This early witness of an unhealthy relationship could have imprinted on Willie a poor example of what a relationship looks like, thus serving as cause for his troubles with love.
Raised With Rhythm
Fortunately for Willie, his grandfather was passionate about music and bought his grandson his first guitar when he was just six years old. A year later, Willie had written his first of many songs using the handful of chords he’d been taught. By the time he was seven years old, Willie was already in a band, playing the guitar with the local group, Bohemian Polka. His childhood was a rural one and Willie hated picking cotton so, from the age of 13, earned a living singing in various local clubs and honky tonks.
Blood, Sweat, And Tears
Not everything went according to plan, however, and when he made his first public appearance, Willie suffered a bout of stage fright. Due to recite a poem in church, the six-year-old Willie got so nervous that he started picking his nose compulsively, causing a nosebleed that stained his smart white suit. The incident earned him one of the many nicknames he would accumulate over the years and many knew him as Booger Red during his formative years. We’ll reveal more about one of his later nicknames, Shotgun Willie, later on.
During his high school days, Willie wasn’t the most outstanding athlete but he loved sport and played on several school teams. As well as playing halfback on the football team, Willie was also active on both the baseball and basketball teams. Willie has continued to live an active life into his maturity and has shown a long-standing interest in martial arts. According to some sources, he’s not only active on the sports field but shows some considerable talent in the bedroom department, as well. Many ladies have made claims to their relationships with Willie, one almost costing him millions.
Willie Gets His Wings
Right after graduating high school, and before Willie had any real girlfriends, Willie joined the airforce in 1950, just as the Korean War was breaking out. His ambition was to become a pilot but, after completing his basic training, he was considered unsuitable as a candidate for the airforce and instead trained as a medic. Despite his youthful love of sport, Willie was discharged after just nine months of service, after back problems caused by his early days in the cotton fields, gained him a medical discharge.
On his return from military service, Willie met & married Martha Matthews. He was 19 years old at the time, but fell head over heels with the sixteen-year-old waitress he met at a drive-in cinema. Reflecting on their relationship, Willie said it was, “the kind of love where you lose your mind and let your heart lead the way”. The two had three children together; Lana, Susie and Willie “Billy” Hugh, Jr. Billy died by suicide in 1991.
Shortly after leaving the Air Force, he found himself at age 22 employed as a disc jockey for a local Texan radio station. While there, he found some old tapes in the studio and recorded his first tracks. The two songs, The Storm Has Just Begun, and When I’ve Sung My Last Hillbilly Song, weren’t good enough according to SARG Records and they rejected them both. But four years later Willie got his chance to prove the record label wrong when his song, The Storm Has Just Begun, was released as a B-side tape.
Willie stayed loyal to his rural upbringing and went to study agriculture at Baylor University. He found the subject uninspiring, however, and dropped out after just a couple of semesters. Determined to pursue a career in music and now with a family to support, Willie took on a variety of odd jobs to keep himself afloat (which included working as a bouncer at a local club and repairing saddles for local equestrians). It was only after his first son was born in 1958 that Willie got his first break as a musician, performing at Esquire Ballroom near Houston.
Hairy Times Ahead
When Willie first started, he had a clean-cut image and kept his hair short and his face clean-shaven, like most of his fellow musicians in the Fifties. It was only in the early Seventies that he decided to let it all hang out, which drove the ladies wild. Soon he realized that his hair needed to be kept under control when he was performing, hence the distinctive braids. Although, Willie’s image changes and personal evolution, brought trouble for his marriage.
Willie’s first marriage collapsed in a dramatic heap. Rumor has it that Martha was so angry with Willie when he passed out drunk one night that she tied him up in ropes and beat him with a broom. Willie also claims that Martha bit him. Though the two had been together 10 years and had three children together, the two divorced in 1962 due to his infidelity. Years later, in 1989 Martha passed away due to liver failure, survived by her three children, Lana, Susie and Billy.
Shirley Comes Along
Something of a serial monogamist, Willie married again soon after his divorce from Martha. His relationship with fellow singer Shirley Collie lasted eight years but ended abruptly after she discovered Willie was paying the hospital bill for another woman who had recently given birth to a baby girl. The other woman proved to be none other than Connie Koepke, who became Willie’s third wife. Ol’ Willie found himself again in the middle of women troubles; forever unlucky in love.
Ready To Retire
After his house burned down in 1969 and his second marriage was coming to a bitter end, things in Willie’s professional life were also taking a turn for the worse. In the early Seventies, after several unsuccessful tours had left him nearly destitute, Willie decided that music wasn’t for him and retired from the industry. Fortunately, his disillusionment didn’t last long and, after moving to Austin, he was inspired by the alternative culture there and decided to pick up his guitar again. Some 45 years later he’s still going strong.
Willie’s third marriage was to Connie in 1971 after the birth of their first daughter, Paula Carlene Nelson. Shortly after Paula’s birth, they welcomed their second daughter Amy Lee Nelson. The two had a happy marriage; Willie’s career was successful as a musician and song writer and Connie lead a successful career as a producer. It seemed like nothing could go wrong and that maybe Willie was finally lucky in love. But then, Willie decided to expand his horizons and go into acting and things for the couple got rocky…
Willie hasn’t always been the peaceful type himself and when he heard that his daughter, Lana, was being abused by her husband, he didn’t hesitate in taking the law into his own hands. Willie drove quickly to his daughter’s marital home and slapped him around a little. The fight escalated when his son in law drove after him, shooting, but Willie was waiting for him and fired his shotgun at the car, making sure his message came across loud and clear.
Willie’s history with women has been up and down, with love and hate in equal proportions. Despite that, Willie has said in the past, “There is no such thing as an ex-wife, there are only additional wives. It’s an accumulation.” Although no one walks away from a marriage without some pain, Willie sees it as a learning experience. He also doesn’t seem to regret any of his marriages, despite saying, “The reason divorces are so expensive is, they’re worth it.” And in 1988 he did just that, had a really expensive divorce with Connie Koepke.
Kiss And Make Up
In addition to his singing career, Willie has appeared in a few movies, including the 1986 Western, Stagecoach. It was on the set of this film that he met his current wife, Ann Marie D’Angelo. Never one to shy away from his feelings, Willie fell hopelessly in love with Annie almost immediately and now, 26 years since their wedding day, says that Annie is, “great love affair in my life”. Determined as he is not to repeat previous mistakes, keeping the marriage together is never easy, especially when you’re Willie.
A Lifetime of Love
Three years after the couple met, Willie and Annie married in Nashville in 1991. Since then, they have stuck by each other through thick and thin. Willie describes himself as a complete romantic and, looking at the pictures of the couple together, it certainly seems that way. He still puts Annie through the ringer occassionally, though, and she’s stayed by his side through his arrests for possession of marijuana and his run-in with the IRS.
It’s not only the IRS that have taken their share of Willie’s possessions. Back in 1969, Willie’s ranch in Tennessee caught fire. Recalling the incident, Willie said, “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 … I was trying to keep the firemen from finding it and turning me over to the police”. Although he saved his precious stash, Willie lost over 100 tapes of songs he had yet to record.
Trial And Error
Despite having been married for a total of 62 years, Willie still hasn’t quite perfected the art of cohabitation. The singer admits, “I’m not easy to live with. I’m pretty temperamental…”. He also acknowledges that, while there used to be a lot of friction between him and his previous wives, things are different with Annie. According to Willie, “…it seems like Annie and I did okay with each other. It takes a special person to live with me”. And to stay put when the skeletons come out of the closet…
The Secret’s Out
One of biggest challenges Annie and Willie have had to endure was the discovery of Willie’s secret family. Six years ago, Willie discovered that a close friend and old flame of his, Mary Haney, had, many years ago, given birth to his daughter. Willie knew nothing of the girl’s existence until 2012 when he found he not only had a daughter he never knew but a granddaughter and great-granddaughter to boot. Willie’s reaction was surprisingly calm, saying, “Mary was a sweet lady, and I’m glad we had a family together”.
Annie also seems to have taken the new additions to Willie’s extensive family in her stride. While Willie and Annie have two children together, this is a drop in the ocean compared to the rest of Willie’s extended family. In addition to his newly discovered daughter, Renee, Willie has fathered eight children and, as they are all growing into mature adults, so his family keeps growing, with grandchildren and great-grandchildren. Sadly, not all Willie’s children are still alive.
Willie’s eldest son, Billy Nelson, was born to his first wife, Martha Matthews, in 1958 when Willie himself was just 25 years old. He followed in his father’s footsteps, and father and son were in the process of recording an album together when Billy tragically took his own life in December 1991. Billy had been battling with an alcohol addiction for some time but Willie had done everything in his power to help his eldest son. At the time, Willie said, “I’ve never experienced anything so devastating in my life”.
Playing for Posterity
Billy isn’t the only of Willie’s offspring to pursue a career in music and his son, Lukas, dropped out of college to dedicate himself to music just as his father did decades before. The son of Annie and Willie is a successful musician in his own right and his band, Lukas Nelson & Promise of the Real, regularly played with Canadian musician Neil Young. Despite his own achievements, Lukas says, “There’s nothing better in life to me than being onstage with my dad”.
Memories for Sale
One of the other setbacks Willie’s experienced in his private life occurred in 1990 when he ran into trouble with the IRS. Between Willie himself and one of his previous managers, money had been severely mismanaged, leading to the IRS seizing assets worth around $32,000 from the country singer. Willie auctioned off numerous personal items to cover the rest of his debt and then released a double-sided album entitled The IRS Tapes: Who Will Buy My Memories, which helped him clear the debt three years later.
Million Dollar Marathon
Nearly 20 years ago, an anonymous woman claimed that she and Willie had engaged in a nine-hour sexual marathon, during which he promised to marry her. The woman in question took Willie to court but to no avail. Although Willie has never admitted to the event or denied it, he did tell Rolling Stones magazine, “I’m not saying it didn’t happen. It might’ve. But you would’ve thought I’d remember at least the first four or five hours”. If it’s true, no wonder he’s had women lining up to marry him.
The Pot And The Kettle
Despite coming from very different backgrounds, rapper Snoop Dogg and Willie have a close relationship. Not only have the pair appeared onstage together, they also had a marijuana smoking competition last year. Snoop was confident he could out-smoke anyone but Willie soon proved too much of a hardened professional for the Dogg. According to Willie, he has an incredible tolerance for the drug, saying, “I can probably smoke with anybody anywhere. Me and Snoop Dogg had a smoke-off in Amsterdam and he crawled away”.
When Willie was a child, he was captivated by the presentation of martial arts heroes in the comic books he sometimes read. Inspired by these characters, he started teaching himself jiu-jitsu. In the Eighties, the singer took up Tae Kwon Do and would practice on his tour bus, sending videos of his moves to his teacher for instruction. By the Nineties, Willie was trying his hand at the Korean method known as GongKwon Yusul and, four years ago, was presented with his fifth-degree black belt at a ceremony in Texas.
Despite how far Willie has come in his professional life, he’s never forgotten his humble rural roots. Back in 1985, he, along with John Mellencamp and Neil Young, set up a non-profit organization called Farm Aid, aimed at raising awareness of the importance of small, family-run farms and providing a disaster fund for small agricultural ventures. As president of the board of directors, Willie is instrumental in organizing the annual fund-raising concerts. This year’s Farm Aid Festival will take place in Hartford, Connecticut in September.
Having grown up in Texas, Willie still owns property there but spends much of his time in an eco-friendly community in Maui. Along with other environmentally aware celebrities, such as Owen Wilson and Woody Harrelson, Nelson owns a home in a village where nearly all the homes rely entirely on solar power and are designed to minimize their carbon footprint. The counterculture atmosphere around Paia was undoubtedly a draw for the country singer and, in addition to his home, he also owns a bar called Charleys, situated on the island.
Friends in High Places
Despite his notoriety and number of arrests, Willie has been long-time friends with former President, Jimmy Carter. When Carter was running the country, Willie was a frequent visitor to the White House and became firm friends with Jimmy’s son, Chip. On occasions, Willie also sang with the president’s wife, Rosalynn, performing Up Against the Wall, Redneck Mother with her on the South Lawn back in 1980. More recently, in 2016, Rosalynn joined Willie onstage in Atlanta, Georgia for a rendition of Amazing Grace.
Willie’s not the only one committed to his new business and his wife Annie has her own range of specialist products. Teaming up with Willie’s Reserve, Annie’s business, Annie’s Edibles, offers hand-crafted chocolates which contain some of the highest-grade cannabis available. The candies use “consciously sourced ingredients” and offer an alternative to those who, like Bill Clinton, prefer not to inhale. According to Annie, “I make my infused chocolates for people who want to enjoy gourmet cannabis chocolate in a controllable way”.
Never one to settle, at the age of 85, Willie is not only still performing, he’s also set up his own agricultural enterprise. Willie’s Reserve is dedicated to providing the best medicinal herbs grown by independent farmers all over America. According to the company website, this “trailblazing line of marijuana products… celebrate Willie’s love of cannabis and the culture surrounding it”. Offering a range of products, from ready rolled to vapes, Willie’s mission is to celebrate the tradition of “sharing, caring and toking”. Don’t go – there’s more still to come.
High on the White House
Willie’s liking for marijuana has been well-publicized over the years and is responsible for another famous story about the man. According to Willie’s autobiography, he was sitting with a companion on the roof of the White House smoking cannabis back in the Seventies. He recalled, “I let the weed cover me with a pleasing cloud … I guess the roof of the White House is the safest place to smoke dope”. Although reluctant to confirm the name of his companion, Willie recently revealed that it was, in fact, Chip Carter.
Missing the Bus
Although Willie now owns several properties, there were many years when he spent more time on the road than at home. When success meant he could afford to stay in a hotel, Willie quickly decided the life of luxury just wasn’t for him and, while his crew were tucked up in their hotel rooms, he would spend the night in his tour bus. Over a period of nearly 40 years, Willie spent roughly six months of each year living and sleeping on his bus. Wonder if he misses it?
On the Road Again
Willie certainly wasn’t born with a silver spoon in his mouth and, during his younger years, often struggled to find enough work to provide for himself and, later, his wife and children. At one stage, Willie decided to go in search of his estranged mother, heading to Portland in Oregon. Hitchhiking from San Diego, Willie struggled to get a life and ended up sleeping in a ditch. While he got to his destination eventually, he has little more to say about his mother and whether or not they reconciled.
Crash Test Willie
One of the other famous stories about Willie’s past is the time he survived an airplane crash. According to a close friend of Willie’s, the singer was flying into a small town near to the location where the epic war movie, Alamo was filmed. As the plane came into land, it hit a pothole in the airstrip and flipped, causing local Happy Shahan to call the press, hoping for some good publicity. Unfortunately for him, both Willie and the pilot survived the incident, limping away from the wrecked plane.
Power of the Pen
Prior to his onstage success, Willie found his talent for songwriting was more likely to pay the bills than his ability as a performer. As you’ll recall from earlier in this article, Willie’s first recordings were rejected, but when he wrote for Billy Walker and Roy Orbison, he achieved his first real success in the music industry. His greatest claim to fame was Patsy Cline’s version of Crazy which he co-wrote with Oliver English in 1961. The song went on to become one of the biggest jukebox hits in history.
Strumming in his Sleep
There’s no disputing that Willie has written and recorded a lot of songs over the years and some might wonder how he’s found time to compose them all. Well, according to his wife Annie, even when he’s sleeping, Willie doesn’t stop playing. Annie says she often sees Willie strumming away while he’s fast asleep, although quite how much he remembers of these compositions, no one knows. At least he has Annie around to remind him of any moments of musical magic that pop up while he’s dreaming.
Horses For Courses
In addition to his Farm Aid involvement, Willie is outspoken in his support of several other causes. As an active member of the National Organization for the Reform of Marijuana Laws, he has been campaigning for the legalization of the controversial herb for years. Willie is also involved in a campaign to make the slaughter of horses illegal in America. Working alongside the Animal Welfare Institute, Willie is pressuring authorities to pass the American Horse Slaughter Prevention Act. The singer even adopted horses from the non-profit agency, Habitat for Horses.
Back on the Bus
Now 85 years of age, Willie is still writing and performing. Although he had to cancel a few concert dates earlier this year, due to ill health, he was back on his bus in no time. After releasing yet another album in April this year, Willie was back on tour with the Outlaw Musical Festival Tour. The Festival is, according to organizer Keith Wortel, “a celebration of everything Willie”. The musicians traveled through North Carolina to Ohio, before their final concert in Texas on 1st July.
Will Willie Survive?
After everything, he’s been through in his life, and all he’s put his wives through, it seems that Willie has finally found a place to lay his head. Despite the news of his secret family and his numerous offspring, it looks like Annie and he will fulfill their marriage vows and remain together until death do them part. Now together in business as well as in matrimony, it would appear the couple have no intention of letting anything come between them and their love for one another.