In 1999, the unexpected union of Billy Bob Thornton and Angelina Jolie made headlines, leaving many in disbelief. Not only did the couple have a significant 20-year age difference, but they were also romantically involved with other partners at the time, adding to the intrigue.
Actress Laura Dern, Billy Bob’s fiancée, was among those caught off guard. Laura revealed that she learned about her partner’s marriage to Angelina at the same time as the public, disrupting her own relationship plans.
Billy Bob and Laura’s relationship began in 1997, following Laura’s split from Jeff Goldblum and Billy Bob’s ongoing divorce from his fourth wife, Pietra Dawn Cherniak, according to E! Online. After two years together, they became engaged and were planning a wedding when Billy Bob met Angelina on the set of Pushing Tin in 1999.
Their whirlwind romance led to a spontaneous wedding in Las Vegas in May 2000, leaving Laura surprised and hurt. Laura later shared her feelings of sudden loss and confusion, stating, “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,” as reported by InStyle.
While Billy Bob never explicitly admitted fault, he expressed regret in a 2001 interview, apologizing for any pain caused, according to the Mirror. He said, “Others may say that you left our girl and married someone else. But it made me happy and somebody else happy. I’m sorry it caused pain.”
Adding an unusual twist to the story, Laura and Angelina had a previous connection, with Laura having babysat Angelina as a child, as detailed by Yahoo. Laura’s father, Bruce Dern, recalled the time, mentioning Laura babysitting Angelina when they were children staying over at director Hal Ashby’s house.
After the breakup, Laura found support from her friend Melissa Etheridge, who recalled helping Laura move out of her shared home with Billy Bob. Melissa recounted the difficult situation, stating on Andy Cohen’s SiriusFM radio show (via the Sun), “I was around when Angelina was not doing nice things with Billy Bob to Laura Dern. I went through that on a personal level, and then to know the side of Jennifer and Brad. I helped Laura move out of her house with Billy Bob — I like broke into their home to get their stuff out because it was so nasty.”
In the aftermath, everyone involved moved forward with their lives. Laura eventually married Ben Harper, with whom she shares two children, and has been linked to former NBA player Baron Davis.
Billy Bob and Angelina divorced in 2002, prompting Billy Bob to shy away from dating celebrities due to privacy concerns. He later married a puppeteer in 2014, seeking a quieter life away from the spotlight.