Rich Bower (OLI "POWER" GRANT) is a powerful New York gangster who wants to leave the criminal world for the flashier one of becoming a hip-hop impresario. Yet, for all of Rich's criminal-based power, he discovers that as a "legit" black man he'll have to play in a white man's world. He and his right-hand man, Cigar (RAEKWON), learn this the hard way when a record producer rejects them based on their appearance and the producer's belief that crime follows the rap/hip-hop scene they're pursuing.
Sam Donager (BROOKE SHIELDS) is an aspiring documentary filmmaker who wishes to investigate and record the phenomenon of white kids who act like they're black and adopt a certain stereotypical black lifestyle. As such, she and her bisexual husband, Terry (ROBERT DOWNEY JR.), beginning following a group of students, including Charlie (BIJOU PHILLIPS), Wren (ELIJAH WOOD), Raven (GABY HOFFMANN) and Will (WILLIAM LEE SCOTT), who's tight with Rich and just so happens to be the son of District Attorney Bill King (JOE PANTOLIANO).
While Rich's lifestyle proves alluring to both Sam and the students she follows, the gangster's parties and get-togethers draw all sorts of people, from boxer Mike Tyson (MIKE TYSON) to up and coming basketball star, Dean (ALLAN HOUSTON), and his girlfriend, Greta (CLAUDIA SCHIFFER), who's big into social anthropology.
Things seem fine until NYPD detective Mark Clear (BEN STILLER) attempts to trap and then blackmail Dean in an effort to get his buddy Rich. Soon, Clear's actions set into motion a series of unavoidable repercussions that will affect the lives of most everyone involved in this group.