How to Be a Player  (1997)

Theatrical Release Information:
How to Be a Player

A man who's devoted his life to running around on his woman finally meets his match in this comedy. Dray Jackson (Bill Bellamy) is a ladies' man par excellence, who never lets the fact that he has a girlfriend, Lisa (Lark Voorhies), get in the way of making time with as many other women as possible. As he spends a typical day going from house to house "visiting" a number of beautiful females, Dray fills his friends David (Pierre Edwards), Kilo (Jermaine Hopkins), and Spootie (A.J. Johnson) in on the finer points of the art of having as many ladies as you want without getting caught. Dray's sister Jenny (Natalie Desselle) and her friend Katrina (Mari Morrow) are at once disgusted and morbidly fascinated with Dray's cheerful, chronic infidelity, and since Jenny is studying anthropology, they decide that Dray's lifestyle would be a worthy subject for research. Deciding to see what would happen if Dray was really put to the test (and maybe teach him a lesson in the process), Jenny and Katrina throw a party, and they invite Dray -- and all the women whose telephone numbers appear in his address book. Max Julien, best known for his role as the ultra-smooth pimp in the blaxploitation classic The Mack, appears as Dray's lady-killing Uncle Fred. ~ Mark Deming, All Movie Guide