Willie Nelson remains a country music powerhouse at 92, continuing to perform and connect with fans after more than seven decades in the spotlight. The Texas native became a household name with classics like “On the Road Again,” “To All the Girls I’ve Loved Before,” and “Pancho and Lefty,” and his legacy extends beyond music — he’s long been a vocal advocate for farmers’ rights, marijuana legalization, and LGBTQ+ equality.

The life I love is makin’ music with my friends… Thanks for having us, Phoenix!
📷: Aubrey Wise pic.twitter.com/oQLI7BvYvb

— Willie Nelson (@WillieNelson) May 15, 2025

His personal life has been just as colorful. The Grammy winner has been married four times — to Martha Matthews, Shirley Collie, Connie Koepke and his current wife, Annie D’Angelo . “I’m not easy to live with,” he admitted to Parade in 2010, reflecting on his multiple marriages. “I’ve been used to doing things my own way for so long that I’m not interested in any suggestions.”

Here’s a closer look at his ex-wives and his lasting relationship with Annie below.

Martha Matthews

When Willie was 19 years old and discharged from the Air Force due to back injuries, he met Martha, who was 16 at the time, per Sunset Blvd Records. They would go on to welcome three children: Lana, Susie, and Willie Nelson Jr. But their home was not a happy one, as the young couple “quarreled, brawled, and drank heavily,” per Parade. The relationship became so volatile, Martha once tied up Willie in a blanket and beat him with a broomstick, according to the Los Angeles Times. Martha denied the story, saying she used a kid’s jump rope instead of a blanket to tie Willie up.

They split in 1962, and according to the Orlando Sentinel, Martha died in 1989 at the age of 53.

Shirley Collie

In 1963, Willie took Shirley for his second bride. Shirley had a successful career as a rockabilly singer, yodeler, guitarist and songwriter. The couple would even often tour together. However, divorce was imminent after Shirley found a bill from the maternity ward of a Houston hospital saying Willie had fathered a baby with another woman, Connie Koepke. “The bill said the charges were for the birth of a baby girl, Paula Carlene, born to a Mrs. Connie Nelson,” Willie recalled in his memoir 2020 “Me and Sister Bobbie: True Tales of the Family Band,” via People. “Shirley wanted to know who in the hell was Connie Nelson. Couldn’t lie. Was caught flatfooted. Had to get the words out of my mouth. ‘Connie’s my girlfriend and Paula’s our daughter.’”

Willie and Shirley divorced in 1971. She died in 2010 at the age of 78.

Connie Koepke

In the same year he divorced Shirley, Willie made an honest woman out of Connie. Two years later, they welcomed another daughter named Amy. Their 16-year marriage would bring Willie back to his home state of Texas, where he felt he was could connect with his fans again.  “I really felt like I needed to be in Texas playing to the people that were and still are my base,” he told Parade. The love affair wouldn’t survive Willie’s affairs, though, and they bid adieu in 1988. “I messed up another marriage. My wandering ways were too much for any woman to put up with,” he admitted in his memoir.

Annie D’Angelo

Willie met makeup artist Annie in 1986 while working on the film Stagecoach. “In the mid-eighties I fell head over heels in love with Ann Marie D’Angelo, called Annie. Never had met a woman like her before,” he wrote in his memoir. The pair married in 1991, and Annie quickly proved to be a steady and grounding presence in his life.

“There was friction with my other wives. But it seems like Annie and I did OK with each other. It takes a special person to live with me,” he told Parade. More than three decades later, the couple remain happily married.