Black and White (1999)

Starring:

• Ben Stiller
• Allan Houston
• Claudia Schiffer

IMDB.com
Set in New York City, Black and White features several losely related stories centering on a pair of documentary filmmakers, Sam and her husband Terry, in following a group of caucasian teens, Raven, Charlie, Will, Marty, Wren and others who try to fit in with Harlem's black hip-hop crowd who include gangster rapper Rich Bower and his music partner Cigar in landing a recording gig, as well as college basketball player Dean who is conflicted on taking a fall on a game for shady gambler Mark Clear who has hidden agenda for Dean and Rich.