Trippin' (1999)

Synopsis
A high-school senior finds himself walking a fine line between daydreams and reality in the comedy Trippin'. Gregory Reed (Deon Richmond) is soon to graduate from high school, and he frequently drifts into a Walter Mitty-style fantasy land where he's the coolest guy in town, has money to burn, and fine ladies are throwing themselves at him around the clock; however, back in the real world, Gregory has a lousy job, no girlfriend, and no solid prospects of a date for the prom. A much bigger worry to his parents is the fact that Gregory has done almost nothing about planning for his future after graduation; he's so preoccupied by his problems with women that he hasn't even started applying to colleges. His best friend, June (Donald Faison), has got girls to spare, but while he has a future ahead of him, it isn't a good one -- he's started selling stolen goods for low-level crime boss Kenyatta (Stoney Jackson). The girl of Gregory's dreams is Cinny Hawkins (Maia Campbell), who's beautiful, smart -- and has a boyfriend. Figuring he'll settle for whatever attention he can get, Gregory asks Cinny if she can help him with his college applications, as she's been through the route and has already been accepted. Cinny agrees, and as she and Gregory become friends, she starts to wonder if her pushy boyfriend is really the guy she wants to take to the prom. Balancing typical teen-flick humor with a pointed message about personal responsibility, Trippin' was a surprise box-office success in the spring of 1999. Director David Raynr's own teenage years included a brief stint as a regular on the TV series James at 15. ~ Mark Deming, All Movie Guide