At the height of his heartthrob fame, Leo was a notorious party monster. He kept a tight group of semi-celebrity guy friends who lived up to the filthy name they gave themselves.

The posse back in their heyday

David Blaine, Leonardo DiCaprio, Tobey Maguire. Click here for the NSFW nude version of this photo, which is probably photoshopped.

Source: membres.multimania.fr

In the late '90s, Titanic had just made Leonardo DiCaprio the most lusted-after heartthrob in the world, and he was enjoying all the rewards of his newfound fame and fortune. DiCaprio kept a close-knit group of guy friends that called themselves "the pussy posse," named after their love of chasing girls and partying. They became New York City nightlife fixtures, with bad-boy behaviors like getting into fights, setting off stink bombs in nightclubs, and worst of all, being notoriously bad tippers to waitstaff.

A 1998 New York magazine article, "Leo, Prince of the City," details the rumors of the posse's exploits. It's full of amazing moments, like Elizabeth Berkeley's boyfriend trying to beat up one posse member who kept calling Berkeley and asking her to dinner and a quote by Sen. John McCain saying "Leonardo DiCaprio ... is an androgynous wimp." The article gets really crazy when the writer convinces a Leo look-alike to drive around Times Square in a limo, sending teen girls into a frenzy.

The posse was made up mostly of child actors who got to know one another growing up in L.A. and seeing each other at the same auditions — DiCaprio himself was a child actor before he hit it big. (The close male friendships stoked the fires of rumor that he was gay or bisexual for years, though it seems it was all just a bromance.)

The posse appears to have remained tight to this day, core members going to Lakers games and red carpets together. Several posse members keep popping up in DiCaprio's films or working behind the scenes for his production company.

It appears the pussy posse didn't break up; it just went legit.