Willie Nelsons new docuseries: From affairs and the death of his son to his IRS struggles

Willie Nelson performing at the New Orleans Jazz and Heritage Festival in 1999. Photo / Getty Images

Willie Nelson knows from experience that it’s funny how time slips away.

In the new four-episode docuseries Willie Nelson & Family by Paramount+, the American musical icon looks back on the incredible highs (platinum and gold-selling albums, world tours and strong family relationships) and the dark lows (publicised affairs, divorce, loss, and health and money struggles) that he’s lived through over the past 90 years.

“It’s hard to believe it was 60 years ago I wrote a song Funny How Time Slips Away,” Nelson says as the documentary comes to a close. “I was only 27, and I really didn’t know what I was talking about.”

The series was filmed at different locations across the country and shares insights from not only Nelson himself, but also his kids, his wife Annie D’Angelo, his former lovers, his late sister Bobbie Nelson (who passed away at 91 last year), his fellow musical pals and lifelong friends.

Here are some of the most eye-opening revelations from the documentary about the small-town Texas boy who became one of the biggest names in musical history, reports People.

A fight with his first wife resulted in a fork in his side

Willie met his first wife Martha Jewel Matthews in 1952 while she was working at a burger joint. Nelson was 19 and she was 16.

“She was a dark-haired beauty, a full-blooded Cherokee,” Nelson reveals in the series. “Her eyes set my soul on fire, and her name was Martha Jewel.”

Around two or three days after they first met, Willie asked Matthews if she would go on a date. Not long afterwards, the pair ran off together and were wed behind her parents’ backs.

“My mother didn’t want me to marry because I was as young as I was, so we just ran off,” Matthews, who died of liver failure in 1989, is heard recounting in a voiceover.

Nelson and Matthews’ daughter Lana says that her mum described the beginning of their relationship as like “Bonnie and Clyde — going through America on their own, not worrying about money, but having to worry about money at the same time”.

However, their relationship wasn’t without the drama of Bonnie and Clyde’s story, either.

“We had a lot of fun together but we fought, and we both were drinking a lot in those days,” Nelson says. “One morning we got in this argument, and she picked up this fork and threw it across the table and it stuck in my side. It sounded like a tuning fork.”

Willie had multiple suicide attempts in his drinking days

In the 1960s, Nelson left Fort Worth, Texas, for Nashville with his wife Matthews and their three children Lana, Susie and Billy. As Nelson played music for little money, the family struggled financially, and Matthews made the decision that she would not put up with “no more crap”.

“She and I were fighting worse than ever, and I started drinking more than ever,” Nelson says. “I would get drunk every night and go home with someone different every night. [I was] slowly self-destructing. I really didn’t care.”

“Back in my drinking days, I tried to commit suicide a couple of times,” he confesses. “One time in the dead of winter I was so down on myself I laid down in the middle of the street hoping a car would run over me. No such luck. I had to get up off my ass and kept on trying to figure out how to make a living.”

Willie felt a sexual vibe while recording Willingly with Shirley Collie

In 1962, while Nelson was estranged from Matthews, he recorded the duet Willingly with singer Shirley Collie.

“The title just about summed up the sexual vibe we felt in the studio,” Nelson says.

After he and Matthews divorced, Nelson went on to marry Collie in 1963.

“From the very beginning there was something about [Shirley] that was after Willie,” Matthews reveals. “I could see it.”

Collie discovered Willie had had an affair when she received a hospital bill for the birth of his mistress’ child

Out of the blue, Collie spotted a Houston hospital bill for the birth of a baby girl, Paula Carlene, born to Mrs Connie Nelson.

“Shirley wanted to know who in the hell was Connie Nelson,” Nelson says. “The truth is Connie [Koepke] had been my girlfriend for several years before becoming pregnant.”

“She had no idea there was a Connie,” adds Lana. “She had no idea there was a baby until she got the hospital bill. That’s how she found out about Connie. That’s how I found out about Connie.”

Koepke recounts “the farthest thing from my mind was getting pregnant and telling my mom and dad.”

“Anyway, it happened,” she says. “Honestly, I was the next one, and I don’t mean that in a bad way, it’s just Shirley wasn’t their mother, she was gone. I bonded with those kids so much. I loved those kids. They all became my kids, too.”

Paula says her mother was “the new girlfriend, then wife”. While it was “hard” for Susie, Lana and Billy, she says “we’re all close”.

“That’s dad’s doing,” she says. “He brought us together as one big tribe.”

Billy saved Paula from a house fire

Just before Christmas in 1970, Willie Nelson’s house in Ridgetop, Tennessee, caught fire. It began in the basement, and Billy saved Paula from her crib in the bedroom at the back after he caught a whiff of smoke. However, when Nelson ran into the burning house, he decided to save his beloved guitar Trigger and “a bag of primo Colombian pot”.

“I wasn’t about to lose a couple of pounds of good pot,” he said.

Willie once got into a shootout with daughter Lana’s ex-husband

When the family was residing in Ridgetop, Lana says she “was married to a guy who had some anger management issues, and he took it out on me”.

“It really pissed me off when he beat her up, so I went over there and slapped him around a little bit,” Nelson says. “I told him not to ever do that again. Then he come back, taking shots at the house.”

Nelson and his late bandmate Paul English responded with guns of their own and shot back at Lana’s former husband’s car.

“We had the whole family there,” Lana recounts. “My mother, who is freaking out, is screaming, ‘Oh my God, oh my God, we’re going to get killed!’”

Koepke says she grabbed a hold of Matthews and instructed her to “get down”.

“That’s how I met Martha,” she says with a giggle.

They shot up Lana’s ex-husband’s car, however he was still able to drive away. “It was a series of near misses,” Lana says.

Willie Nelson had to have his lung inflated after it collapsed

In 1981, Willie’s lung collapsed while he was in Hawaii. After running for an hour, he went for a dip in the sea, and the pounding of the ocean along with the drastic and sudden temperature change caused his lung to collapse.

He recounts the moment he got out of the water and lay in the sand for around 30 minutes trying to get enough air into his lungs to get up and walk back to the hotel to call the paramedics.

When the paramedics eventually arrived, they stuck a tube through his back, up through his rib cage and into his lung to inflate it. They had to do it two times again the following day.

He has some regrets about his love life — but none about marrying Annie

When Nelson featured in the movie Stagecoach with Johnny Cash and Kris Kristofferson in 1986, producers asked the musician to cut his hair in order to play Doc Holliday. His now-wife Annie D’Angelo was his hair and makeup artist on the film set, and she recalls telling him: “Mr Nelson, I’m the makeup artist. The producer and the director would like to know if you’d be willing to cut your hair for this film.”

D’Angelo says Nelson then asked her what she thought he should do, and she said, “Honestly, I don’t see the point”.

“So he said, ‘Let’s tell them no’,” D’Angelo reveals. “Right then we had this little connection. He taught me dominoes on the bus, and we just really connected.”

Talking about D’Angelo, Nelson says, “I never had met a woman like her before. She was whip-smart with a keen appreciation for all forms of art. She was pretty and radiated enough energy to light up any room she entered. I fell head over heels in love with Anne Marie D’Angelo.”

After divorcing Koepke in 1988, Nelson wed D’Angelo in 1991 and the pair welcomed two sons Lukas and Micah.

“I’ve always said there’s no such thing as a former wife,” Nelson reveals. “Once in your life a wife never leaves. I regret the pain I caused Connie, and Martha and Shirley before her. I have no excuses. I’d be hard-pressed to define love.

“I know God’s love is pure, but worldly love is flawed love, and lots of times confused love. When it came to romance, I had a gift for complicating things, but marrying Annie wasn’t complicated at all. It’s about the smartest thing I ever did.”

He refused to file for bankruptcy during his struggles with the IRS

Nelson discovered in 1990 that he owed US$32 million ($51m) in income taxes to the IRS. “It seemed like a lot of money, but it was a challenge,” he says.

The government had seized all of his property and shut down his studio.

“He was devastated,” Nelson’s nephew Freddy Fletcher reveals. “I’d never seen him so down.”

Nelson’s problems with the IRS began in 1976, when funds came in from Red Headed Stranger. Nelson’s business manager at the time, Neil Reshen, didn’t pay any taxes. Reshen would file extensions while not paying anything down, according to business manager Mark Rothbaum,

In 1978, Rothbaum says Willie fired Reshen. He then made a comeback in 1978 with his album Stardust, which Rothbaum says made him some “serious money”.

Rothbaum reveals Nelson owed a couple of million in taxes in the early 1980s. When Ronald Reagan became president in 1981, tax shelters became fashionable and people started investing in films and cattle feeding as write-offs.

Nelson then enlisted the help of an accountant who advised him that US$200,000 ($318,000) would satisfy his tax problem, and Rothbaum says Nelson replied with, “Okay”.

A few years later, Nelson received letters saying the write-offs were a sham, and the tax bill was in fact $32m ($51m).

Nelson says he was told to file for bankruptcy, but “that wasn’t my plan at all”.

“I never intended and never will do a bankruptcy where the people I owe get screwed out of their money,” he says.

Despite his financial struggles, Nelson still stayed optimistic.

“It’s very important to think positive,” he says. “More important probably is knowing that a negative thought will release poison into your system and will eventually kill you if you keep doing it.”

Nelson and D’Angelo’s nuptials also took place amidst his dilemma with the IRS.

“The lawyer was like, ‘You know he’s $32m in debt and 19 of it will be yours?’ I was like, ‘Yeah, but I’m not here for money either way’,” D’Angelo recalls.

“I already had my own, I was fine, how can I help? I know he came off as super calm, but he wasn’t that calm inside. We had two kids – it was super, super stressful. They seized our house. We were living in this little condo all four of us because Micah was a baby. It was frustrating.”

Fortunately, his mates were able to save his guitar Trigger from the IRS’ possession, and Bobbie saved their piano. Farmers whom Willie had helped at his Farm Aid festival also bought back his ranch for him.

With his IRS tapes, Nelson paid the IRS a dollar every time one was sold.

Billy’s death left a lasting mark on the family

Nelson lost his son Billy in 1991, who passed away by suicide at the age of 33.

“We were 17 months apart,” Susie says. “We did everything together, but he had a lot of issues. They became more and more.”

Lana reveals that her brother struggled with depression.

“He didn’t want to be depressed, he didn’t want to be that guy,” she says. “He tried really hard, he did.”

Paula goes on: “He really was a wonderful guy, but it’s hard to be in Texas when your dad’s Willie Nelson. You can’t get away from it ... When Billy passed, it was terribly hard on him — on all of us. It was really hard for him because that was his first son.”

Rothbaum says Billy felt “that his father had been exploited too often by too many people. Life was hard for him.”

Nelson’s sister Bobbie reveals she and her brother became even closer after Billy’s death.

“It’s not that we had long talks about our grief — that’s not Willie’s way,” she says. “We didn’t have to talk about it. We knew.”

Looking back on his father’s life and reflecting on his ups and downs, Nelson’s son Lukas says, “Dad has been homeless, he’s had his house burnt down, he’s been through four marriages, he’s been up and down, he’s been broke, he’s [fought] the IRS, he’s lost a child ... that’s what makes him inspiring to me: His resilience in the face of adversity.”

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