▁Natal ie ▁D ess elle ▁and ▁Bern ie ▁Mac . ▁The ▁film ▁was ▁directed ▁by ▁Lion el ▁C . ▁Martin , ▁and ▁written ▁by ▁Mark ▁Brown ▁and ▁Dem et ria ▁Johnson . ▁ ▁The ▁How ▁to ▁Be ▁a ▁Player ▁Sound track , ▁released ▁by ▁Def ▁Jam ▁Record ings ▁on ▁August ▁ 5 , ▁ 1 9 9 7 , ▁featured ▁the ▁hit ▁single ▁" Big ▁Bad ▁M amma " ▁by ▁Fox y ▁Brown ▁featuring ▁Dru ▁Hill . ▁ ▁Plot ▁ ▁D ray ton ▁" D ray " ▁Jackson ▁( B ill ▁Bell amy ), ▁who ▁works ▁as ▁an ▁A & R ▁representative ▁for ▁Def ▁Jam ▁Record ings , ▁is ▁a ▁play boy ▁with ▁only ▁one ▁goal ▁in ▁his ▁life : ▁to ▁have ▁sex ▁with ▁as ▁many ▁women ▁as ▁possible . ▁He ▁dream t ▁that ▁he ▁got ▁caught ▁che ating ▁on ▁his ▁girl friend , ▁Lisa , ▁( L ark ▁Voor h ies ) ▁only ▁to ▁w ake ▁up ▁for ▁the ▁dream ▁to ▁rem ind ▁him ▁not ▁to ▁get ▁caught . ▁The ▁women ▁he ▁sle eps ▁with ▁are ▁all ▁a ▁secret ▁from ▁Lisa , ▁who ▁comes ▁over ▁to ▁his ▁house ▁for ▁a ▁bit ▁to ▁see ▁him , ▁before ▁heading ▁off ▁for ▁work . ▁D ray ' s ▁sister , ▁Jen ny , ▁( N atal ie ▁D ess elle ) ▁also ▁came ▁by ▁to ▁his ▁house ▁to ▁rem ind ▁him ▁about ▁the ▁cook out . ▁D ray ▁becomes ▁fasc in ated ▁with ▁Jen ny ' s ▁friend ▁K atr ina ▁( M ari ▁Mor