Year Released: 1991
Directed By: John Singleton
Starring: Cuba Gooding, Jr., Ice Cube, Larry Fishburne, Morris Chestnut, Nia Long and Angela Bassett

Lets see, we've got the baggy jeans, chambray shirt, and plenty of crew neck tees, sweatshirts and snapbacks to go around. Cuba Gooding Jr.'s basketball jersey over a white T is a classic. This film not only showcased the struggles and triumphs of everyday life in Black America, but also the style that would influence a generation.