For some women, having two men fight over them is a dream. For others, like Elizabeth Berkley, it meant an impending lawsuit. Berkley found herself at the center of a huge controversy in 1998 when she caught the eye of Leonardo DiCaprio while she was seeing her then-boyfriend Roger Wilson. The “Titanic” actor had reportedly flirted with the former sitcom star at the premiere of his film “The Man in the Iron Mask,” but she refused his advances. DiCaprio didn’t budge, however, and continued to call Berkley, much to Wilson’s dismay. Wilson ended up confronting DiCaprio, leading the latter to tell his posse to “kick his a**,” according to court documents obtained by Entertainment Weekly.
After the brawl, Wilson alleged he suffered a blow to his throat, preventing him from future singing roles. He filed suit against DiCaprio in 2003, asking for $15 million in compensatory damages and $30 million in punitive damages for the lost opportunities. The lawsuit against the “Wolf of Wall Street” star was ultimately thrown out, however, with Judge Paula Omansky admitting that it could move forward against Todd Healy, who had confessed to hitting Wilson.
While Berkley was merely a pawn in the ordeal, some speculate that it painted her in a bad light. On top of battling sexist backlash from “Showgirls,” the actor was once again at the mercy of powerful Hollywood higher-ups. DiCaprio’s distaste over the debacle could have rubbed off on Berkley, making it that much harder to be taken seriously in the industry.
