Let me tell you about Willie Nelson’s new docuseries, Willie Nelson & Family, which just premiered on Paramount+ on December 21. This series takes fans deep into the life of the legendary country superstar. You get an exclusive peek behind the scenes of his family life, including a close-up look at his current wife, Annie D’Angelo. But here's the question on everyone's mind: how many wives has Willie Nelson had throughout his lifetime?

How Many Times Has Willie Nelson Said "I Do"?

Now, Willie Nelson’s love life has had its fair share of ups and downs. Over the years, he's been married four times, with Annie D’Angelo being his fourth and current wife. His first marriage was to Martha Matthews back in 1952 when he was just 19 years old. That chapter closed in 1962. Not long after, in 1963, Willie tied the knot again, this time with Shirley Collie. But their marriage hit a rocky patch when Shirley discovered Willie's affair with Connie Kopeke, leading to their split in 1971. Willie wasted no time and married Connie the same year. However, another affair caused a rift, and they eventually divorced in 1988. Willie found love again with Annie, and they've been together since their wedding in 1991.

Why Did Willie Nelson's Marriages End?

In his memoir co-written with his sister, Bobbie Nelson, Willie opens up about his past infidelities, which played a significant role in the end of his marriages. While married to Shirley, Willie received a hospital bill that initially seemed like a minor issue. But as it turns out, the bill was for the birth of a baby girl named Paula Carlene, born to a Mrs. Connie Nelson. This revelation shook Shirley, and Willie couldn’t deny the truth. Connie and Willie welcomed Paula in 1969, and they had another daughter in 1971. For 16 years, things seemed to be going well. But then Willie met Annie on the set of his TV movie Stagecoach, and an affair began, leading to his divorce from Connie in 1988.

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Willie Nelson sits on stage next to wife Annie D'Angelo — Suzanne Cordeiro / Getty Images

Who Exactly Is Annie D’Angelo?

Willie and Annie’s story began on the set of his TV movie Stagecoach, where Annie worked as a makeup artist. They quickly bonded and started spending time together, often hanging out with fellow country legends Johnny Cash and June Carter. In his memoir, Willie describes his intense feelings for Annie, acknowledging that winning her heart wasn’t easy. He had to prove that his previous marriage was truly over and that he was ready to start anew.

“Annie wasn’t impressed by my fame. She’s incredibly intelligent, with a deep appreciation for all forms of art. Not to mention, she’s beautiful and has an energy that lights up any room she enters. She also has a sharp political sense,” Willie fondly recalls. The couple went on to have two sons in 1988 and 1990 before they officially exchanged vows in 1991. Today, the retired makeup artist splits her time between Hawaii and Texas, where they own a ranch together.