Def Jam's How to Be a Player (1997) is an American sex comedy starring Bill Bellamy, Natalie Desselle, and Bernie Mac. Directed by Lionel C. Martin, it follows Dray Jackson (Bill Bellamy), a playboy working at Def Jam Recordings, as he tries to juggle multiple women without getting caught. His sister Jenny (Natalie Desselle) and her friend set him up, hoping to expose his ways. The film's soundtrack features the hit single "Big Bad Mamma" by Foxy Brown featuring Dru Hill. In the end, Dray gets caught by his girlfriend, Lisa, after a final setup.🖤👑🎬🎥 Cast Bill Bellamy — Drayton "Dray" Jackson Natalie Desselle — Jennifer "Jenny" Jackson Lark Voorhies — Lisa Mari Morrow — Katrina Pierre Edwards — David Bernie Mac — Buster Bebe Drake - Mama Jackson Jermaine 'Huggy' Hopkins — Kilo Anthony Johnson — Spootie Max Julien — Uncle Fred Beverly Johnson — Robin Gilbert Gottfried — Tony the Doorman Natashia Williams - Girl in Pink at Malibu party Stacii Jae Johnson — Sherri Elise Neal — Nadine J. Anthony Brown — Uncle Snook Amber Smith — Amber Jerod Mixon — Kid #1 Jamal Mixon — Kid #2