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Def Jam's How to Be a Player is a 1997 American sex comedy film, starring Bill Bellamy, Natalie Desselle and Bernie Mac. The film was directed by Lionel C. Martin, and written by Mark Brown and Demetria Johnson. The How to Be a Player Soundtrack, released by Def Jam Recordings on August 5, 1997, featured the hit single "Big Bad Mamma" by Foxy Brown featuring Dru Hill. Plot Drayton "Dray" Jackson (Bill Bellamy), who works as an A&R representative for Def Jam Recordings, is a playboy with only one goal in life: to have sex with as many women as possible. He dreams that he gets caught cheating on his girlfriend, Lisa, (Lark Voorhies) only to wake up from the dream to remind him not to get caught. The women he sleeps with are all a secret from Lisa, who comes over to his house for a bit to see him, before heading off for work. Dray's sister, Jenny, (Natalie Desselle) also comes by his house to remind him about the cookout. Dray becomes fascinated with Jenny's friend Katrina (Mari Morrow), and invites her to a party his friend is hosting; she tells him that she is busy. Jenny cannot stand Dray's way of treating women. As soon as Dray leaves, she and Katrina snoop around and find Dray's mobile black book of his women. Jenny plans to set Dray up at the party in a hostile environment, hoping that Dray, if he gets caught, will reform his ways. After Jenny and Katrina call the women and receive their numbers, they both leave. Dray makes his daily rounds of sex with his women, including his three main ones: Robin (Beverly Johnson), a married woman, Amber (Amber Smith), a sexy thespian, and Sherri (Stacii Jae Johnson), a freaky dominatrix. Afterwards, Dray goes to the cookout briefly before continuing on to the party. When he sees all of the women there, including Jenny and Katrina, he understands that he has been set up by them. He figures out a way get all of the women out of the party, without them noticing about each other and confrontation about Dray. He then heads to Jenny and Katrina to explain that when a player is put in a hostile environment, a player doesn't reform: he adapts to the situation. Dray leaves to go home and wait for Lisa to come see him after a long day at work. While Dray is waiting for Lisa, Katrina shows up at the last minute to apologize. However, she has become fascinated with Dray and has been fantasizing about him. Before leaving, she makes a move on Dray and they have sex, apparently fulfilling her fantasy. Lisa returns, but Katrina is able to leave without her noticing. However as Lisa changes into her nightwear, she sees a dress, bra, and heels with smears of lipstick spelling out: "Busted, Adapt." Realizing that Katrina has set him up, Dray knows that he finally got caught. 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 Soundtrack References External links How to Be a Player at IMDb How to Be a Player at the TCM Movie Database Def Jam's How to Be a Player at Letterboxd How to Be a Player at AllMovie Def Jam's How to Be a Player at Rotten Tomatoes. Discover the Jenny Jackson popular books. Find the top 100 most popular Jenny Jackson books.