A scholarship student (Jasmine Guy) is introduced to Will, opening up a new world of fun---to divert her from her studies. Will: Will Smith. Carlton: Alfonso Ribeiro. Vivian: Janet Hubert-Whitten. Geoffrey: Joseph Marcell.
Will crawls to Philip for help after sneaking out on the town and getting hustled by sleazy pool sharks. Charlie the Mack: J.D. Hall. Fred: Hugh Dane. Gloria: Angela Gordon. Louie: Jeff Chayette. Philip: James Avery.
On a bet with Will, Carlton tries to survive in Jazz's rough neighborhood by parading as a financial consultant. Slick: Miguel Nunez. Jazz: Jeff Townes. Tiny: "Tiny" Lister Jr. Chuck: J'vonne Pearson. Will: Will Smith.