Country music star Willie Nelson has been married four times in his lifetime, but his marriage to his current wife is by far his longest.
The "Highwayman" crooner, 91, has confessed he's "not easy to live with" and yet Annie D'Angelo, 67, has been by his side since they tied the knot in 1991.
An age difference of 23 years has proved to be a success for the couple, but what do we know about the love of Willie's life?
Willie and Annie bonded over his hair
Willie and Annie first met in 1986 on the set of his TV movie Stagecoach. She was a makeup artist and according to the New York Times, they bonded over his infamous long hair.
The outlet revealed that Annie agreed with her future husband, that he shouldn't have to cut his braids for the role.
© Getty ImagesRomance didn't blossom right away, however, as Willie was still married to his third wife, Connie Koepke.
"She had to be sure my marriage was over and that I was truly free," he wrote in his memoir Me & Sister Bobbie.
He divorced Connie in 1988.
Willie can be challenging
© Getty ImagesWillie has said that he's "not easy to live with," and says he's "temperamental," and "used to doing things my own way."
This didn't deter Annie. "There was friction with my other wives," Willie told Parade. "But it seems like Annie and I did okay with each other. It takes a special person to live with me."
She calls Texas and Hawaii home
© Getty ImagesAnnie splits her time between their two homes while Willie is on the road. Their primary residence is in Spicewood, Texas, where he has lived since the 80s.
They also have a property in Maui, Hawaii, where they raised the two children they share and they entertain celebrity guests such as Woody Harrelson.
Annie is a mom to two sons
© Getty ImagesWhile Willie has fathered eight children, he only shares two with Annie.
Lukas, born in 1988, and Mica, born in 1990, are their grown-up sons.
They're both musicians like their famous dad and have carved out successful careers for themselves.
© Getty Images"We've got a couple of great kids," Willie told People. "I am proud of them and all they're doing on their own. It's great to have your kids with you at any time, but if they're on the stage singing with you and they're good, that makes it even better."
Annie had an edibles business
© Getty ImagesAnnie got into the marijuana business in 2017 and launched her line of edible chocolates under Willie's Reserve label.
Willie supported his wife's venture and said: "The thing about edibles is you need to know what you're getting into. Annie's chocolates are clean, I trust the dosage and I happen to love them."
She's his everything
© Getty Images"I call her my pet rattler," Willie said of Annie in an interview with People. "She's my lover, my wife, nurse, doctor, bodyguard."
The key to their success is laughter, according to the singer. "I've always enjoyed a good joke," he said, and added: "As they say, laughter's the best medicine."
Willie also gushed about Annie to Rolling Stone in 2022, telling the outlet: "She's been with me through thick and thin — you can't ask for anything more than that!"
