Trippin' (1999)

Starring:

• Deon Richmond
• Donald Faison
• Guy Torry
• Maia Campbell
• Aloma Wright
• Harold Sylvester
• Cleavon McClendon
• Bill Henderson
• Michael Warren
• Countess Vaughn
• Stoney Jackson
• Dartanyan Edmonds
• Anthony Anderson

Storyline

A high-school senior, Gregory Reed (Deon Richmond) is unprepared for life after graduation. Obsessed with finding a girlfriend, Gregory often has elaborate fantasies where he imagines himself as a successful ladies' man. While Gregory passes the time with his slick, trouble-seeking friend, June (Donald Adeosun Faison), he can't seem to escape his rut until he meets the pretty and brainy Cinny (Maia Campbell). Although his crush already has a boyfriend, Gregory is intent on winning her over.