In the world of Hollywood, there is no shortage of shocking love stories. One such tale that took everyone by surprise was the marriage of Billy Bob Thornton and Angelina Jolie in 1999. The couple not only had a significant 20-year age gap but were also involved with other partners at the time. This unexpected union left many, including actress Laura Dern, bewildered and heartbroken.

Laura Dern, who was engaged to Billy Bob at the time, found out about their wedding at the same moment as the public, throwing her relationship plans into disarray. Laura and Billy Bob had been together since 1997 after both of them had gone through breakups. They were happy and preparing for their own wedding when fate took a turn.

It was on the set of the movie Pushing Tin in 1999 that Billy Bob crossed paths with Angelina Jolie. Their connection was instant, and their romance escalated quickly, leading to a spontaneous wedding in Las Vegas in May 2000. The sudden turn of events left Laura feeling abandoned and confused, without any closure.

Reflecting on this tumultuous period, Laura shared her feelings, saying, “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.” The sense of sudden loss and unanswered questions left her devastated.

While Billy Bob never explicitly admitted any wrongdoing, he did express regret in a 2001 interview, acknowledging the pain caused by the situation. He stated, “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.”

Strangely enough, Laura and Angelina had a prior connection. Laura had babysat Angelina when they were children, adding an intriguing layer to the story. Bruce Dern, Laura’s father, recalled the time, saying, “I remember Laura babysat one night for Angelina when Angelina was 2 and Laura about 8 … because Jon [Voight] and I were doing Coming Home. They were staying over at [director] Hal Ashby’s house, so they asked [Laura] to come over [to watch Angie].”

After the breakup, Laura found solace and support from her friend Melissa Etheridge, who helped her move out of the shared home with Billy Bob. Melissa revealed, “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, all parties involved moved on with their lives. Laura eventually married Ben Harper, with whom she has two children, and has been linked to former NBA player Baron Davis. Billy Bob, on the other hand, retreated from dating celebrities due to privacy concerns. He later married a puppeteer in 2014, seeking a quieter life away from the spotlight.

The complexities of love and relationships in Hollywood are often stranger than fiction. Laura Dern’s story is a reminder that even in the glamorous world of showbiz, hearts can be broken, plans can be shattered, and unexpected twists can occur.

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