How many times was Billy Bob Thornton married? All about actor’s relationships as he recalls marriage to Angelina Jolie 

The Oscar-winning filmmaker and actor, Billy Bob Thornton, in a recent interview with Rolling Stone, opened up about his relationship and marriage to the Academy Award-winning actress Angelina Jolie.

During the Rolling Stone interview, published on November 17, 2025, Thornton, who made his mark in Hollywood and gained global fame after writing and directing the 1996 thriller drama film Sling Blade, revealed that he still has love for the Original Sin actress and that they are still good friends even after their divorce.

The 70-year-old Billy Bob Thornton, who was married to Angelina Jolie for three years, from 2000 to 2003, opened up about what it was like to be married to her. According to E! News, the Bad Santa actor, Thornton, who was married six times, said:

"Angelina and I had a great time together. That was one of the greatest times of my life. She and I are still very, very close friends."

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Billy Thornton shares how the media reacted to his and Angelina Jolie's relationship

Billy Bob Thornton also shared how difficult it was for him and Jolie to go anywhere and how something they said would be misconstrued by the media. Billy Bob Thornton, while talking about how they had "a really civilized breakup", the actor-director, who is also a singer-songwriter, went ahead and shed light on how the media reacted to his marriage with Jolie. Billy said:

It "was pretty weird."

He continued:

"When we met, I was the more famous one. And then when we got together, for some reason, the people and the media are very interested in celebrity couples, that seems to be a very popular thing."

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Angelina Jolie continues to love Thornton

According to E! News, Angelina Jolie also had the same feeling about Thornton, even after their divorce. The Girl, Interrupted actress, Jolie, in a 2008 Entertainment Weekly interview, regarding Thornton, said:

"I still love him dearly and think the world of him. And I'm proud to have been his wife for a time."

She further added:

“I don't believe in regrets. It's a dangerous habit to get into—it makes you pause in your life if you start thinking back and questioning yourself."

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Let's take a look at Billy Bob Thornton's relationships

As mentioned earlier, Thornton, who was married six times, has had numerous relationships over the years. Let's take a closer look at all his past relationships.

Connie Angland

Thornton is currently married to actress Connie Angland, whom he met in 2004, after his split from Angelina Jolie. While Billy and Connie got hitched in 2014 after dating for a long time, they share a daughter, Bella.

Angelina Jolie

As mentioned earlier, the former famous couple, who had a highly publicized and controversial relationship, were married from 2000 to 2003. They were supposed to adopt son, Maddox, in 2002; however, it was Jolie who eventually adopted him on her own.

Laura Dern

Dern and Billy Bob Thornton began their romance and started dating in 1997. The Goliath actor was still in a relationship with the Jurassic Park actress, Laura Dern, while he was married to Jolie.

Pietra Dawn Cherniak

Cherniak and Thornton were married for four years from 1993 to 1997. He shares two sons, Harry and William, with the former Playboy model, Pietra Dawn Cherniak.

Cynda Williams

Billy Bob Thornton met Cynda during the production of the 1992 thriller film One False Move. While they tied the knot in 1990, Williams and Thornton eventually split.

Toni Lawrence

While Lawrence and Thornton got hitched in 1986, the two eventually split in 1997, finalizing their divorce in 1998.

Melissa Lee Gaitlin

Billy shares a daughter, Amanda, with Melissa. The two got hitched in 1978 and divorced in 1979.