Billy Bob Thornton Dating History: Angelina Jolie and More

Billy Bob Thornton has been married six times, but once declared his intention to stop at five marriage ceremonies.

During a 2008 interview with Maximthe Oscar winner said he “probably won’t” tie the knot again, noting he thought it would be best for his then-girlfriend. Connie England.

“I told Connie I didn’t want to go through with it. We do well. We have 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 him, ‘No. 6.”

Despite his reservations, Thornton married Angland in 2014 and they have been together ever since. The couple have a daughter, Bella, who they welcomed in 2004.

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Before settling with England, 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 Florida Innocence Project began representing Amanda in 2015, claiming the child’s death was completely accidental. She was released from prison in 2020 after serving 8 and a half years.

Tony Lawrence

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

Cynda Williams

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

Pietra Dawn Cherniak

Thornton and the first Playboy The model married in 1993 and welcomed sons William and Harry in 1993 and 1994, respectively. They divorced in 1997.

Laura Dern

At the end of his fourth divorce, Thornton began dating Dern in 1997. He then met Jolie on the set of the 1999 film Postponement of the tin and secretly married him in 2000 while he was still dating Dern.

“I left our house to work on a movie and while I was away, my boyfriend got married and I never heard from him again,” Dern said. talk magazine in 2000, for ABC. “It’s like a sudden death. Because no one has had any closure or clarity.”

Angelina Jolie

Jolie and Thornton’s romance was controversial from the start. After spontaneously marrying 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’s reaction to them — while speaking to students at Loyola Marymount University in 2014.

“We were very separated because she is not doing Tomb Raider and i am doing Monster Ball. … She thought it would be interesting and romantic if we took a little razor and cut our fingers, put some blood on these cabinets. And you wear it around your neck like you wear your baby son or daughter’s hair in one. Same thing,” he explained. “From this, we wore 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 herself. She and Thornton separated in 2002 and divorced the following year.

“I remember our time together was really 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 still not together, maybe because of a different path in life that we wanted to follow.”

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

Connie England

Thornton met Angland shortly after he and Jolie divorced. They welcomed daughter Bella in 2004, but didn’t marry until 2014. During a 2015 appearance on The Late Late Show with James CordenThornton said the couple decided to marry mainly because of their daughter.

“After a while, it was like, ‘Why haven’t my mom and dad gotten married in 12 years?'” he explained. “The reason I didn’t want to (get married at first) is that my marriages have always been very short and I don’t like trying to fix things that aren’t broken. I said, ‘Look, I have a pretty bad record and things are going well.'”

While marriage wasn’t as important to her for the sixth time, Thornton has credited England with pulling her out of a slump when they met on the set of the movie. Bad Santa Claus in 2003.

“(Connie’s) sister Carrie was a makeup artist Bad Santa Clausand she said, ‘My sister is going to visit, and I had a feeling you’d really like her.’ And, of course, I did. And we were together within maybe a few months. She kind of (pulled) me out of the gutter, which was great,’ Thornton said during a November 2024 appearance on The Drew Barrymore Show. “We’ve been together longer than if you put the other five (marriages) together, that’s more time.”