8) Two Can Play That Game (2001)
Director: Mark Brown
Starring: Morris Chestnut, Vivica A. Fox, Anthony Anderson, Mo’Nique
Morris Chestnut is the undisputed king of black romantic comedy genres (have you seen that man’s IMDB page? Date night central!), and this is one of his finest performances as a man who is being strung along by his girlfriend, played by Vivica A. Fox. Take note: The rules laid out in this film have been treated as gospel by the many who have seen it. Oh, and it should be mentioned, now starring Oscar-winning actress, Mo’Nique.
7) The Wood (1999)
Director: Rick Famuyiwa
Starring: Omar Epps, Richard T. Jones, Taye Diggs, Malinda Williams, Tamala Jones
Director Rick Famuyiwa nails his debut with this coming-of-age story focusing on three men —Mike (Omar Epps), Slim (Michael T. Jones), and Roland (Taye Diggs) — one of whom is about to get married. On Roland’s wedding day, the three of them rehash their awkward junior high and high school years, the stage when boys and girls are just starting to understand they will never understand one another.