Once upon a time, Leonardo DiCaprio was a fringe child actor known for his precocious performances in indies like This Boy’s Life, The Basketball Diaries, and What’s Eating Gilbert Grape. Then that little scamp boarded the Titanic and became the King of the World.

When DiCaprio became a bona fide heartthrob for drawing Kate Winslet like one of his French girls, he was officially a grown man of 23. But something happens to a person who has had a job since the age of 5. Their transition into adulthood is corrupted. Leo was suddenly the most desired young actor in Hollywood, with piles of disposable income. He surrounded himself with a posse of other young male actors. Though they were at various stages of success, they shared their fierce loyalty to Leo and a penchant for going buck wild.

Nancy Jo Sales introduced Leo’s boy gang to the world via 1998’s “Leo, Prince of the City”. The now legendary NY Mag piece details some of their more infamous antics. The internet is rife with the finer points of their often-horrifying shenanigans. This list covers the most egregious moments of their privileged antics.

Here are 20 Things You Didn’t Know About Leonardo DiCaprio’s ’90s Boy Gang.

February 23, 2018
Categories: Listicles . Tags: andy cohen, ari gold, david blaine, david letterman, don's plum, elizabeth berkeley, entourage, ethan suplee, harmony korine, jay r. ferguson, jeremy piven, kate winslet, kevin connolly, leonardo dicaprio, lukas haas, meryl streep, ny mag, pussy posse, Roseanne, sara gilbert, screenrant, spring breakers, the basketball diaries, titanic, tobey maguire, watch what happens live . Author: Baxter . Comments: Leave a comment