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Billy Bob Thornton has been married and divorced many times.
Yes, even by Hollywood standards.
Some of these entanglements lasted longer than others. And some ended more bitterly than others.
Here’s a recap of Thornton’s marital history, famous and forgotten. Plus, where things stand today.
Billy Bob Thornton’s first marriage was to Melissa Lee Gatlin
In 1978, Billy Bob Thornton married Melissa Lee Gatlin.
The short-lived marriage ended in 1980, with Gatlin accusing Thornton of adultery in her divorce petition.
However, in 1979, the couple welcomed their daughter, Amanda Brumfield. She is most famous for serving 9 years in prison before being freed by The Innocence Project.
His marriage to Toni Lawrence lasted for only about a year, really
In 1986, Thornton married Toni Lawrence.
It was not a happily ever after.
The following year, they separated. Thornton and Lawrence divorced in 1988.
Billy Bob Thornton married and divorced Cynda Williams
In 1990, Billy Bob Thornton married Cynda Williams, an actress.
She was part of the cast of the 1992 film, One False Move. That film was his writing debut.
Speaking of 1992, that was also the year in which their marriage came to an end.
He had two children with Pietra Dawn Cherniak
In 1993, Thornton and Pietra Dawn Cherniak married.
He and the Playboy model had two sons, William Langston Thornton (born in June 1993) and Harry James Thornton (born in June of 1994).
The marriage came to an end in 1997. Cherniak accused Thornton of spousal abuse, alleging that it sometimes took place in front of their children.
Thornton neither married nor divorced Laura Dern
Beginning in 1997, Billy Bob Thornton began dating beloved actress Laura Dern.
Reports and rumors have claimed that the two became engaged. However, that is not the truth.
The relationship ended in 1999. By the sound of it, it may have outlasted at least one of his marriages.
And, of course, Billy Bob Thornton and Angelina Jolie married in 2000
In 2000, Thornton married Angelina Jolie following their shared project, 1999’s Pushing Tin. She is nearly 20 years his junior.
This is perhaps Thornton’s most infamous relationship, which may be saying a lot. The two packed on the PDA with great enthusiasm. They also wore lockets that contained a single drop of each other’s blood. This romantic gesture spurred unhinged rumors about the two of them, and prompted some of the earliest hate towards Jolie.
In June of 2002, the couple separated, divorcing the following year. Despite March 2002 announcements that they had adopted a child from Cambodia, it turned out that Jolie had adopted Maddox as a single parent.
His longest-ever relationship has been with Connie Angland
In 2003, Billy Bob Thornton began dating Connie Angland, a makeup effects artist on the set of Bad Santa. In 2004, they welcomed a daughter, Bella Thornton.
For over a decade, they opted to forego marriage. Thornton’s history of getting married and divorced so many times was, to be blunt, discouraging.
However, in October of 2014, he and Angland married. It was largely spurred by their daughter. Despite his track record — which Thornton himself admits was not so good — they remain together and married in 2025.
Sixth time’s the charm?