Synopsis

A group of affluent white teenagers in New York pursue close ties with Harlem's hip-hop community, treating its music, style, and street reputation as an ideal. Their fascination brings them into contact with aspiring rapper Rich Bower, a troubled basketball player, and a morally compromised detective. Meanwhile, a documentary filmmaker records the uneasy exchanges, exposing questions about race, identity, privilege, sexuality, and cultural appropriation.

Factoids & Trivia

• Much of the dialogue was improvised. The filmmakers gave performers objectives for individual scenes rather than fully written lines, while the sequences involving Allan Houston, Claudia Schiffer, Ben Stiller, and Joe Pantoliano were reportedly scripted in full.

• The production mixed established actors with real hip-hop figures, including members of Wu-Tang Clan and Onyx. Their presence helped give the film's music-world scenes a more immediate, documentary-like texture.

• Mike Tyson's involvement began with an accidental meeting. Toback encountered Tyson in a New York restaurant while thinking about how to contact him for the film and approached him about appearing.

• Tyson plays himself, while his reflective conversations about violence, fame, prison, and humiliation became some of the film's most frequently discussed scenes.

• The film premiered at the Telluride Film Festival on September 4, 1999, and was subsequently shown at the Toronto International Film Festival on September 15, 1999. It opened in U.S. theaters on April 5, 2000.

• Brooke Shields wore fake dreadlocks and temporarily pierced her nose for her documentarian character. Claudia Schiffer had her ears pierced for the large hoop earrings worn in the film.

• The soundtrack combines original hip-hop material with older soul, pop, reggae, and classical recordings, reflecting the film's deliberately eclectic view of New York's music and social worlds.

• With an estimated $12 million budget and worldwide box-office earnings of about $5.5 million, the film became a commercial disappointment despite its unusually high-profile blend of actors, musicians, athletes, and celebrity appearances.