In 1999, the unexpected marriage of Billy Bob Thornton and Angelina Jolie made headlines and surprised many people.
The couple had a notable 20-year age difference and were both involved with other partners at the time, which added to the excitement.
One person who was shocked was actress Laura Dern, who was engaged to Billy Bob. Laura found out about Billy Bob’s marriage to Angelina at the same time as everyone else, which upset her plans.
Billy Bob and Laura started dating in 1997, right after Laura split from Jeff Goldblum and Billy Bob was still going through a divorce from his fourth wife, Pietra Dawn Cherniak. After two years together, they were engaged and planning their wedding when Billy Bob met Angelina on the set of “Pushing Tin” in 1999.

Billy Bob Thornton and Angelina Jolie’s quickie wedding in Las Vegas in May 2000 took many by surprise, including Laura Dern. Laura was caught off guard and shared her feelings in an interview with InStyle: “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.” She felt a sudden sense of loss and confusion with no closure.
Billy Bob never admitted to any wrongdoing but did express regret in a 2001 interview, saying: “Others may say that you left our girl and married someone else. But it made me and somebody else happy. I’m sorry it caused pain.”
In a strange twist, Laura and Angelina had a past connection; Laura had babysat Angelina when they were children, according to Yahoo.

Laura Dern’s father, Bruce Dern, recalled a time when Laura babysat Angelina Jolie. He explained that since he and Jon Voight were working on the movie “Coming Home” in 1978, Laura, who was about 8 years old at the time, watched 2-year-old Angelina at director Hal Ashby’s house.
After Laura and Billy Bob broke up, Laura received support from her friend Melissa Etheridge. Melissa shared on Andy Cohen’s SiriusXM radio show that she helped Laura move out of her home with Billy Bob, even having to break into their house to retrieve Laura’s belongings. Melissa added that she had witnessed some of the difficulties Laura faced due to Billy Bob’s relationship with Angelina.
Following these events, Laura moved on with her life. She married Ben Harper and has two children with him, and has also been linked to former NBA player Baron Davis.
Billy Bob and Angelina divorced in 2002. Billy Bob decided to avoid dating celebrities after this, seeking a quieter life. He later married a puppeteer in 2014, aiming for more privacy.
What are your thoughts on this situation? Share your comments below!
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