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Billy Bob Thornton, the Academy Award winner, has amassed both critical acclaim and the audiences’ love. He’s a man of many talents, from acting, to singing, and even screenwriting. Thornton has proven himself through multiple projects likeSling BladeandMonster Ball, but one aspect of his life has been a little rocky.
He’s been married six times now, and five of his previous marriages have ended in a divorce. But despite the highs and lows in his love life, Thornton has shown up for his children and co-parented them with his exes. After a few low-key and some high-profile romances, he seems to have found his happily ever after. So let’s take a closer look at the actor’s journey through love and heartbreak, which eventually led to a marriage that has now lasted for years.
Melissa Lee Gatlin: Billy Bob Thornton’s First Wife
Billy Bob Thorntonmarried Melissa Lee Gatlin in 1978, and the couple tied the knot after a whirlwind romance. However, the relationship did not last long, as it ended in a controversial divorce. The two parted their ways in 1980, and the reasons were incompatibility and adultery (viaMarried Celeb).
Even though their marriage was short-lived, the duo welcomed a daughter named Amanda, who was born in 1979. Despite the challenges he faced in his first marriage, it remains a lesser-known chapter of his life, at least in the public eye.
Billy Bob Thornton Walks Down The Aisle With Toni Lawrence
Billy Bob Thornton was hopeful even after the failure of his first marriage, and he decided to wed Toni Lawrence, six years after the prior divorce. Lawrence and Thornton decided to spend their lives with each other and married in 1986, but shortly after, things seemed to have become difficult between the two.
They kept their lives private and remained tight-lipped about the reason that led them to part ways, and finalize their divorce in 1988 (viaThe Little Facts). Lawrence, who was known for her roles inMcCloudandPigsdecided that it was best to step out of the limelight after the seperation. But on the other hand, Thornton kept working in the industry, slowly laying the groundwork to build more opportunities for himself.
Cynda Williams: Billy Bob Thornton’s Third Divorce
In 1990, Billy Bob Thornton remarried the beloved actress, Cynda Williams. The duo met while on the film set ofOne False Movewhich Thornton co-wrote. It was clear that the two shared both personal and professional relationships, as Williams also starred in the film asLila Walker. However, their short-lived romance came to an end in 1992, when the couple divorced.
Williams continued working in the industry and carved out a path for herself. She went on to become an author and activist, and both of them seemed to move on with their own lives. Their relationship, which began with a creative collaboration, couldn’t handle the pressure of working in show business.
Pietre Dawn Cherniak: A Tumultuous Marriage
A year after his divorce from Williams, Thornton was already in another relationship and married Pietre Dawn Cherniak, a Playboy model in 1993. Their marriage lasted for five years and was perhaps the most controversial relationship of Thornton’s life.
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It was Cherniak who filed for divorce, and reportedly accused the actor of spousal abuse (viaLegit). This news made headlines in the 90s and was heavily covered by the media. The ex-couple share two sons together and Thornton has remained active in their lives, but Pietra chose to not be in the public eye and focused on raising her kids.
A High Profile Marriage With Angelina Jolie
Billy Bob Thornton’s marriage toAngelina Joliewas the most publicized one, and comparatively, the most discussed relationship amongst all the ones he had earlier. The two met on the sets ofPushing Tinin 1999 and quickly became the talk of the town (viaGrazia).
Their relationship seemed to be passionate and eclectic and they were often in the news for the eccentric ways in which they showed each other affection, like wearing a vial of each others’ blood around their necks. However, their marriage happened to be short and intense as they said their vows in 2000, and separated in 2002. The divorce was finalized in 2003, and according to Thornton the reasons behind their split was their conflicting lifestyles.
Angelina Jolie seemed to be more outgoing whereas Thornton enjoyed living the life of a recluse, enjoying the quieter moments. Despite their differences, he only has good things to say about her and the duo remained close friends even after their failed marriage.
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In this time period, Jolie was already a global icon and went on to adopt her first child, Maddox, as a single parent. Thornton was still focused on his career and continued to build it with critically acclaimed projects as he navigated the challenges of fame and his love life.
Connie Angland: Billy Bob Thornton’s Present Wife
After five of his marriages ended in divorce, Thornton was understandably hesitant about tying the knot again. But then he met Connie Angland, a makeup and special effects artist, who became an exception in his life (viaPeople). They met shortly after his divorce from Angelina Jolie, and the duo soon began dating.
This time around, Thornton kept his romance low-key, and a decade after being together, he married Angland in a private ceremony on July 11, 2025. Their intimate home in Los Angeles was the perfect location for their wedding, away from all the glitz and glamour of Hollywood. Since their marriage, the couple has led a private lifestyle and smartly avoided the pitfalls of being in the spotlight.
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Their daughter, Bella Thornton was born in 2004, and the family seems to have found stability and balance together. Thornton now prioritizes his family life while still pursuing his creative endeavors, and feels no pressure about maintaining a public image. So, for the first time in decades, he has found a partnership that feels grounded, lasting, and fulfilling, and achieved the happy ending that most desire.
Sonika Kamble
Articles Published :1195
Sonika Kamble is an entertainment writer at Fandomwire, covering everything from timeless classics to newly released movies. With over 1000+ articles published, she delves into breakdowns, think pieces, speculations, and more.She enjoys connecting the dots and covering newfound angles about characters, scenes, and themes from movies directed by Scorsese, Fincher, Tarantino, Linklater, and other exceptional filmmakers.
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