Starring: John Leguizamo, Nestor Serrano, Doug E. Doug, Mario Joyner

New Line Cinema began the 1990s as the studio known for urban, coming-of-age one-nighter tales, starting with 1990’s House Party and followed by the indie sleeper Hangin’ with the Homeboys, featuring rising talents and helmed by the late Joseph Vasquez.

Four Uptown friends—sweet supermarket clerk Johnny (Leguizamo), “Italian-passing” womanizer Fernando (Serrano), aspiring actor Tom (Joyner), and eager, wise activist Willie (Doug)—head downtown for a night out. When plans go awry, their evening forces them to question the bonds they took for granted.

Released during the decade’s indie boom, amid films increasingly fixated on urban plight and violence, Hangin’ with the Homeboys offered an antidote of sorts, recreating the rite-of-passage touchstones more often seen in films like Diner or American Graffiti. As Roger Ebert aptly put it: “Young urban males are often seen only in terms of the fears they inspire, instead of for who they really are. These are nice kids. Maybe that’s the message.”