All the Bombshells in Willie Nelson’s New Docuseries, from Affairs and the Death of His Son to His IRS Struggles

Wille Nelson knows firsthand that it’s funny, how time slips away.

In the new four-episode Paramount+ documentary series Willie Nelson & Family (streaming now), the icon looks back on the extraordinary highs (platinum- and gold-selling albums, worldwide tours and strong family ties) and dark lows (affairs, divorce, loss and money and health struggles) he’s experienced over the past 90 years.

“It’s hard to believe it was 60 years ago I wrote a song ‘Funny How Time Slips Away’,” Willie says at the end of the series. “I was only 27, and I really didn’t know what I was talking about.”

Willie Nelson & Family promo art.

Paramount+

Presented by MTV Entertainment Studios, 101 Studios, Blackbird Presents Films and Sight Unseen, the series was filmed throughout the country and features insights from not only Willie himself, but also his children, his wife Annie D’Angelo, his former loves, his late sister Bobbie Nelson (who died at age 91 in 2022), his fellow musicians and his lifelong friends.

Below, the most eye-opening moments from the series about the small-town Abbott, Texas, boy who became one of the most beloved musicians in history.

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

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

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

Two or three days after they met, Willie asked Matthews to go out. It wasn’t long before they ran off and got married without her parents knowing.

“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, says in a voiceover.

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

It wasn’t without the drama of Bonnie and Clyde’s relationship, either.

“We had a lot of fun together but we fought, and we both were drinking a lot in those days,” Willie 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 ’60s, Willie left Fort Worth, Texas, for Nashville with Matthews and their three kids Lana, Susie and Billy. As Willie gigged for little money, the family struggled, and Matthews says she decided she would not put up with “no more crap.”

“She and I were fighting worse than ever, and I started drinking more than ever,” Willie 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 continues. “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.”

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Willie felt a sexual vibe while recording “Willingly” with Shirley Collie

While estranged from Matthews, Willie recorded the duet “Willingly” with singer Shirley Collie in 1962.

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

After he got divorced from Matthews, Willie married Collie in 1963.

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

Willie Nelson and ex-wife Shirley Collie in 1962.
Johnny Franklin/andmorebears/Getty

Collie learned Willie had had an affair when she got a hospital bill for the birth of his mistress’ baby

One day, Collie saw a bill from a Houston hospital 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,” Willie 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.” 

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Koepke says that at the time, “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 mom 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

Right before Christmas in 1970, Willie’s house in Ridgetop, Tennessee caught on fire. The fire started in the basement, and Billy saved Paula from her crib in the back bedroom after he smelled smoke. Willie, meanwhile, ran into the burning house and rescued 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 says. 

Willie Nelson and his family in 1981.
Paul Harris/Getty

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

While the family was living 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,” Willie says. “I told him not to ever do that again. Then he come back, taking shots at the house.”

Willie and his late bandmate Paul English went out with guns of their own and shot back at Lana’s ex’s car.

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

Koepke says she grabbed Matthews and told her to “get down.”

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

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

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Willie had to have his lung inflated after it collapsed

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

He recalls getting out of the water and laying in the sand for 20 to 30 minutes trying to get enough air to get up and walk to the hotel room and call paramedics.

When the paramedics 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 twice again the next day. 

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

When Willie filmed Stagecoach with Johnny Cash and Kris Kristofferson in 1986, producers asked him to cut his hair to play Doc Holliday. His now-wife Annie D’Angelo was his hair and makeup artist on the film at the time, 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 Willie then asked her what she thought, and she said, “Honestly, I don’t see the point.”

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

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Of D’Angelo, Willie 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, Willie married D’Angelo in 1991 (The two share sons Lukas and Micah).

“I’ve always said there’s no such thing as a former wife,” Willie says. “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.” 

Willie Nelson and his wife Annie D’Angelo in 2000.
LUCY NICHOLSON/AFP via Getty

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

In 1990, Willie learned he owed $32 million 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 closed down his studio.

“He was devastated,” Willie’s nephew Freddy Fletcher says of his uncle. “I’d never seen him so down.”

The IRS situation started in 1976, when funds came in from Red Headed Stranger, but Willie’s business manager at the time Neil Reshen didn’t pay any taxes. According to business manager Mark Rothbaum, Reshen would file extensions while not paying anything down.

In 1978, Rothbaum says Willie fired Reshen. He then hit it big again with his album Stardust in 1978, which Rothbaum says earned him “serious money.”

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In the early ’80s, Rothbaum says Willie owed a couple million in taxes. When Ronald Reagan became president in 1981, tax shelters became vogue, and people were investing in movies and cattle feeding as write-offs.

Willie then went to an accountant who suggested $200,000 would satisfy his tax dilemma, and Rothbaum says Willie said, “Okay.”  

In the late ’80s letters came saying the write-offs were a sham, and the tax bill was $32 million.

Willie says he was advised 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 troubles, Willie tried to keep 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.”

Willie and D’Angelo’s wedding also happened amidst his struggles with the IRS.

“The lawyer was like, ‘You know he’s $32 million 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, friends were able to save Trigger from the IRS’ possession, and Bobbie was able to save their piano. Farmers whom Willie had helped through his Farm Aid festival also bought back his ranch for him.

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

Willie Nelson’s IRS Tapes cover.

Billy’s death left a lasting mark on the family

In 1991, Willie lost his son Billy, who died by suicide at age 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 says her brother suffered from 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 adds: “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.”

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Willie’s sister Bobbie says that after Billy’s death, she and her brother grew even closer.

“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.” 

Summing up his father’s life, Willie’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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Source: HIS Education