Billy Bob Thornton’s Dating History: Angelina Jolie and More

Billy Bob Thornton has been married six times, but he once stated his intention to stop at five wedding ceremonies.

During a 2008 interview with Maxim, the Oscar winner said that he would “probably not” tie the knot again, noting that he thought it would be best for his then-girlfriend Connie Angland.

“I told Connie I didn’t want to put her through that. We do fine. We’ve been together for four years now. We have a child together,” Thornton said at the time. “If we get married, then the press will start calling her, ‘No. 6.’”

Despite his reservations, Thornton married Angland in 2014, and they’ve been together since. The couple share daughter Bella, whom they welcomed in 2004.

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Prior to settling down with Angland, Thornton had relationships with A-listers including Angelina Jolie and Laura Dern. Keep scrolling for a look at his dating history:

Melissa Lee Gatlin

The actor was married to Gatlin from 1978 to 1980. In 1979, they welcomed daughter Amanda, who was sentenced to 20 years in prison in 2008 for the death of her friend’s one-year-old-daughter. The Innocence Project of Florida began representing Amanda in 2015, claiming that the child’s death was entirely accidental. She was released from prison in 2020 after serving 8 and a half years.

Toni Lawrence

Thornton married Lawrence in 1986, but their union was short-lived; the pair separated in 1997 and divorced in 1998.

Cynda Williams

Thornton married Williams in 1990 after meeting her on the set of his writing debut One False Move. They divorced before the film’s release in May 1992.

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Pietra Dawn Cherniak

Thornton and the former Playboy model tied the knot in 1993 and welcomed sons William and Harry in 1993 and 1994, respectively. They divorced in 1997.

Laura Dern

On the heels of his fourth divorce, Thornton began dating Dern in 1997. He then met Jolie on the set of the 1999 film Pushing Tin and secretly married her in 2000, while he was still dating Dern.

“I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again,” Dern told Talk magazine in 2000, per ABC. “It’s like a sudden death. For no one has there been any closure or clarity.”

Angelina Jolie

Jolie and Thornton’s romance was controversial from the start. After spontaneously tying the knot in Las Vegas, the couple raised eyebrows in 2001 when they started wearing necklaces filled with each other’s blood. Thornton addressed the necklaces — and the public reaction to them — while speaking to students at Loyola Marymount University in 2014.

“We were apart a lot because she’s off making Tomb Raider and I’m making Monster’s Ball. … She thought it would be interesting and romantic if we took a little razorblade and sliced our fingers, smeared a little blood on these lockets. And you wear it around your neck just like you wear your son or daughter’s baby hair in one. Same thing,” he explained. “From that, we were wearing quart jars of blood around our necks. And we were vampires and we lived in a dungeon.”

Thornton and Jolie, who had a 20-year age gap, announced their plans to adopt son Maddox in 2002, but Jolie later finalized the adoption on her own. She and Thornton separated in 2002 and divorced the following year.

“I remember our time together as really being great,” Thornton said of Jolie during a 2018 interview for the “HFPA in Conversation” podcast series. “We just had different lifestyles. Hers is a global lifestyle and mine is an agoraphobic lifestyle. So, that’s really — that’s the only reason we’re probably not still together, maybe, because of a different path in life we wanted to take.”

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Thornton later said that he and Jolie remained “good friends” during a 2019 Tribeca TV Festival screening of Goliath.

Connie Angland

Thornton met Angland shortly after he and Jolie divorced. They welcomed daughter Bella in 2004 but didn’t tie the knot until 2014. During a 2015 appearance on The Late Late Show With James Corden, Thornton said that the couple decided to get married largely because of their daughter.

“After a while, it was like, ‘Why aren’t my mommy and daddy married after 12 years?’” he explained. “The reason I didn’t want to [get married initially] is, my marriages were always very short, and I don’t like to try to fix things that aren’t broken. I said, ‘Look, I got a pretty bad record, and things are going fine.’”

While marriage wasn’t so important for him the sixth time around, Thornton has credited Angland with getting him out of a slump when they met on the set of Bad Santa in 2003.

“[Connie’s] sister Carrie was a makeup artist on Bad Santa, and she said, ‘My sister’s gonna visit, and I got a feeling that you’re really gonna like her.’ And, sure enough, I did. And we were together within probably a couple of months maybe. She kind of [dragged] me out of the gutter, which was awesome,’” Thornton said during a November 2024 appearance on The Drew Barrymore Show. “We’ve been together longer than if you totaled up all the other five [marriages], it’s more time.”