Leonardo DiCaprio and Tobey Maguire have been friends since they were up-and-coming child stars. The two first played friends in This Boy’s Life in 1993, and 20 years later, they costarred in 2013’s The Great Gatsby. However, they also starred together in a small independent movie filmed in 1995 and 1996, featuring members of what Vanity Fair dubbed “DiCaprio’s club-hopping, skirt-chasing group of friends, known collectively as the P*ssy Posse.” The group included numerous notable members aside from DiCaprio and Maguire, including Kevin Connolly and street magician David Blaine.

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