Not only did the couple share a significant 20-year age gap, but they were also both involved with other partners at the time, adding to the intrigue.

Billy Bob and Laura’s relationship began in 1997, shortly after Laura’s split from Jeff Goldblum and Billy Bob’s ongoing divorce from his fourth wife,

Pietra Dawn Cherniak, per E! Online. After two years together they were engaged and preparing for a wedding when Billy Bob crossed paths with Angelina on the set of Pushing Tin in 1999.

Their whirlwind romance culminated in a spontaneous wedding in Las Vegas in May 2000, catching Laura off guard. Reflecting on the abrupt turn of events, Laura shared (via 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.” The situation left her feeling a sense of sudden loss and confusion, with no closure in sight.

While Billy Bob has never explicitly acknowledged any wrongdoing, he did express regret in a 2001 interview, stating, per the Mirror: “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.”

Adding an odd twist to the narrative, Laura and Angelina had a prior connection, with Laura having babysat Angelina when they were children, Yahoo detailed.

Laura’s father, Bruce Dern, recalled that time. “Jon Voight’s a friend of mine, so I remember Laura babysat one night for Angelina when Angelina was 2 and Laura about 8 … because Jon and I were doing Coming Home,” Bruce said referring to the 1978 movie. “They were staying over at [director] Hal Ashby’s house, so they asked [Laura] to come over [to watch Angie].”

Following the breakup, Laura received support from her friend Melissa Etheridge, who recounted helping Laura move out of her shared home with Billy Bob.

Speaking with Andy Cohen on his SiriusFM radio show, Melissa said (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 since been linked to former NBA player Baron Davis.

Billy Bob and Angelina divorced in 2002, prompting Billy Bob to retreat from dating celebrities due to privacy concerns. He later married a puppeteer in 2014, trying to seek a quieter life away from the spotlight.