Leonardo DiCaprio has never needed to bend over backwards to make friends, thanks to access reserved only for Hollywood’s elite, a global fandom and a multi-million-dollar net worth. Even in the 1990s, when his career was just getting started, Leonardo DiCaprio was able to gather an adoring crew of aspiring actors and former child stars around him.
DiCaprio and his motley crew of ’90s bad boys were infamous for their womanizing escapades and they got into a lot of trouble. None of the group’s audacious exploits come close to being as ridiculous as the incident involving Elizabeth Berkley from Saved By The Bell.
The infamous incident, which began when Berkley turned down Leo and his posse’s invitation to dinner, quickly turned into a fight between Berkley’s boyfriend and the posse, and it ended with Leo and his crew being hit with a $45 million lawsuit.
Roger Wilson, Elizabeth Berkley’s ex-boyfriend, filed a $45 million lawsuit against Leonardo DiCaprio and his posse
Roger Wilson filed a lawsuit shortly after the event, accusing DiCaprio of inciting his pals to assault him. Wilson claimed in the complaint that the attack effectively ended his career as a rock frontman and demanded $15 million in compensatory and $30 million in punitive damages.
Todd Healy, a longstanding member of DiCaprio’s posse, admitted in court that he attacked Wilson in self-defence after seeing him reaching for what could’ve been a concealed weapon.
Despite admitting, DiCaprio’s claim was eventually dismissed in September 2004. As reported by Today, the judge who dropped the case reasoned that Healy hadn’t been within earshot when DiCaprio reportedly instructed his posse to “kick [Wilson’s] a**,” and so couldn’t have been incited to attack Wilson.
Decades later, DiCaprio’s group of bad boys has long past its heyday, with many of its founding members having been excommunicated from the group or having lost contact with DiCaprio for different reasons. However, the Titanic actor appears to be determined to catch on to the remnants and makes an effort to hang out with them on occasion.