Willie Nelson’s new docuseries Willie Nelson & Family hit Paramount+ on December 21 and takes a closer look at the country superstar’s life. In it, fans see behind the scenes into his family life, including a look at his current wife, Annie D’Angelo. But how many wives has Willie had in his lifetime?

How Many Wives Has Willie Nelson Had?

Willie’s been married a few times over the years, and Annie marks his fourth. He first married Martha Matthews in 1952 when he was only 19 years old. They called it quits in 1962. Just one year later, Willie tied the knot with his second wife, Shirley Collie, but eventually split in 1971 when Shirley discovered the “On the Road Again” singer’s affair with Connie Kopeke. Willie married Connie the same year that he divorced Shirley, but another of his affairs ruined the relationship, and they went their separate ways in 1988. Willie married Annie in 1991 and the couple is still together.

Why Did Willie Nelson’s Marriages End in Divorce?

In his memoir with sister Bobbie Nelson, Willie revealed some surprising details about his infidelity in the past. While married to Shirley, Willie received a bill from the hospital. At first the “Always on My Mind” singer tried to play it off as though it was a bill for some minor injury.

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

“Shirley wasn’t buying that for one simple reason: The bill said the charges were for the birth of a baby girl, Paula Carlene, born to a Mrs. Connie Nelson,” Willie wrote in the book. “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.’ ”

Connie and Willie welcomed a daughter in 1969, two years before he divorced Shirley. The couple went on to have another daughter in 1971, and all was well in the family for 16 years. However, Willie met current wife Annie on the set of his TV movie Stagecoach. The two indulged in an affair for two years before Willie and Connie divorced in 1988.

Who Is Annie D’Angelo?

After Willie and Annie met on set while Annie worked as a makeup artist, the two began hanging out with fellow country singers Johnny Cash and June Carter.

“My love for Annie was all-consuming, but winning her over wasn’t easy. She had to be sure my marriage was over and that I was truly free,” Willie recalled in the memoir. “She didn’t care about me being a celebrity. She was whip-smart, with a keen appreciation for all forms of art. It didn’t hurt that she was pretty and radiated enough energy to light up any room she entered. She also had a sharp political sense.”

The “Highwayman” singer and Annie went on to have two sons in 1988 and 1990 before they officially said “I do” in 1991. The retired makeup artist splits her time between Hawaii and Texas, where she and Willie own a ranch together.