Having experienced six marriages, Billy Bob Thornton once expressed his intention to stop at five weddings. During a conversation with Maxim in 2008, the Oscar-winning actor indicated that he would likely refrain from marrying again, believing it was in the best interest of 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,” he shared. “If we get married, then the press will start calling her, ‘No. 6.’”
The actor’s romantic escapades include a whirlwind with Angelina Jolie (@angelinajolie/Instagram)
Despite his earlier hesitations, Thornton and Angland tied the knot in 2014 and have remained together since. They are parents to Bella, who was born in 2004.
Before committing to Angland, Thornton had high-profile relationships with celebrities such as Angelina Jolie and Laura Dern. Below is a detailed look at his romantic history:
Melissa Lee Gatlin
From 1978 to 1980, the actor was married to Gatlin. In 1979, their daughter Amanda was born, who, in 2008, was sentenced to 20 years in prison following the tragic death of her friend’s one-year-old daughter.
The Innocence Project of Florida began advocating for Amanda in 2015, asserting that the child’s death was accidental. Amanda was released from prison in 2020 after serving eight and a half years.
Toni Lawrence
Thornton entered into matrimony with Lawrence in 1986, but their marriage proved to be brief; they separated in 1997 and finalized their divorce in 1998.
Cynda Williams
In 1990, Thornton married Williams after they met on the set of his screenwriting debut, One False Move. Their marriage ended in divorce before the film was released in May 1992.
Pietra Dawn Cherniak
The actor tied the knot with former Playboy model Cherniak in 1993, and the couple welcomed two sons, William and Harry, in 1993 and 1994, respectively. Their marriage ended in 1997.
Laura Dern
After his fourth divorce, Thornton began dating Dern in 1997. Shortly thereafter, he met Jolie on the set of the 1999 film Pushing Tin, and they secretly wed in 2000 while he was still in a relationship with 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 stated in a Talk magazine interview in 2000, as reported by ABC. “It’s like a sudden death. For no one has there been any closure or clarity.”
Angelina Jolie
The romance between Jolie and Thornton was marked by controversy from the outset. After a spontaneous wedding in Las Vegas, they raised eyebrows in 2001 by wearing lockets containing each other’s blood. Thornton later addressed the public’s reaction during a talk 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 difference, announced plans to adopt son Maddox in 2002, but Jolie later completed the adoption alone. Their separation occurred later that same year, and their divorce was finalized in 2003.
Billy Bob Thornton and Angelina Jolie (@angelinajolie/Instagram)
“I remember our time together as really being great,” Thornton reflected on 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.”
Thornton mentioned during a 2019 Tribeca TV Festival screening of Goliath that he and Jolie maintained a “good friendship” after their divorce.
Connie Angland
Following his split from Jolie, Thornton met Angland. They welcomed daughter Bella in 2004 but delayed marriage until 2014. During a 2015 appearance on The Late Late Show With James Corden, he shared that the couple decided to marry mainly 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.’”
Although Thornton didn’t feel marriage was essential during his sixth attempt, he credited Angland with helping him overcome a difficult period in his life after 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 recounted 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.”
