In 1999, the world was shocked by the unexpected union of Billy Bob Thornton and Angelina Jolie. The fact that they were both committed to other partners at the time, combined with their significant 20-year age difference, made their marriage even more intriguing. It was a marriage that captured the attention of the public and left many wondering how such a surprising union came to be.

At the time of their marriage, Billy Bob was engaged to actress Laura Dern, who was completely blindsided by the news. She found out about their wedding at the same time as the public, throwing their relationship plans into disarray. Laura, who had started dating Billy Bob in 1997 after her split from Jeff Goldblum, never expected such a sudden turn of events.

Their whirlwind romance began when Billy Bob crossed paths with Angelina on the set of Pushing Tin in 1999. Despite being engaged to Laura, Billy Bob couldn’t resist the connection he felt with Angelina. Their spontaneous wedding in Las Vegas in May 2000 left Laura completely caught off guard. She recalls her shock and confusion, 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.” It was a situation that left her with a sense of loss and no closure.

Although Billy Bob has never explicitly acknowledged any wrongdoing, he did express regret in a 2001 interview. 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.”

What makes this situation even more complex is the prior connection between Laura and Angelina. Laura actually babysat Angelina when they were children. Laura’s father, Bruce Dern, reminisced about that time, mentioning that Laura babysat for Angelina when she was 2 years old and Laura was about 8. This adds an interesting twist to the story and highlights the small world in which they all lived.

After the breakup, Laura received support from her friend Melissa Etheridge, who helped her move out of the house she shared with Billy Bob. Melissa recalled the difficulty of the situation, saying, “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 years that followed, everyone involved moved on with their lives. Laura eventually married Ben Harper and has two children. On the other hand, Billy Bob retreated from dating celebrities and married a puppeteer in 2014, seeking a quieter life away from the spotlight.

This situation reminds us of the complexities of relationships and the unexpected turns they can take. It serves as a reminder that even in the world of celebrities, love and heartbreak are universal experiences.

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