Plot
Before the opening credits begin, a dedication to Yusuf Hawkins is shown, who was killed on August 23, 1989, in Bensonhurst, New York, by neighborhood folk who believed the youth was involved with a white girl in the neighborhood, though he was actually in the neighborhood to inquire about a used car for sale in the area.
Flipper Purify (Wesley Snipes) is a successful, married African American man who works at an architectural firm in New York City. One day, an Italian American woman named Angela "Angie" Tucci (Annabella Sciorra) is hired as a temporary secretary at the place. Flipper complains to his partners Jerry (Tim Robbins) and Leslie (Brad Dourif) about wanting an African American secretary; they tell him that they want "the best human being for the job."
When Flipper returns to his Harlem home after visiting his friend Cyrus (Spike Lee), he tells his wife Drew (Lonette McKee) about his promotion. Drew tells him to be prepared if his promotion is declined, but Flipper tells her not to worry. Meanwhile, Angie returns to her Bensonhurst home, and cooks dinner for her father Mike (Frank Vincent) and her two brothers Charlie (David Dundara) and Jimmy (Michael Imperioli). Her boyfriend Paulie Carbone (John Turturro) arrives and takes her out on a date.
One night, Flipper and Angie are working late at the firm, and they start to have a conversation about cooking. They have dinner in his office and have sex on a desk. The next day, Flipper does not say anything when he is walking his daughter to school. Later, at the office, he tells Jerry and Leslie that he wanted to be partner at the firm. After his offer is declined, he abruptly quits his job. Later that night at the park, Flipper admits his infidelity to Cyrus, who tells him the affair is problematic not only because his mistress is white, but also because she is Italian and from Bensonhurst. Then, Flipper's brother Gator (Samuel L. Jackson) shows up with his girlfriend Vivian (Halle Berry). He asks Flipper for some money so he can feed his crack habit. Flipper initially refuses, but gives in eventually. Meanwhile, Angie tells her girlfriends that she is seeing Flipper, shocking them when she tells them he is African American. She then tells them not to tell anybody.
The next evening Flipper and Angela are ignored by the staff at a restaurant. He complains to a waitress (Queen Latifah) about not being served; she in turn berates him for dating a white woman. Later, the rumors about them surface when Flipper comes home and sees a furious Drew throwing his things out of the window, forcing him to move back in with his mother Lucinda (Ruby Dee), and his father, the Good Reverend Doctor (Ossie Davis). Later that night, he confronts Cyrus for betraying his trust. Cyrus admitted he told his wife Vera (Veronica Webb), but did not know she told Drew. Flipper insults Vera, causing a rift in his friendship with Cyrus.
The next day, Flipper tries to make things up to Drew by bringing her flowers at work, which she proceeds to refuse. Meanwhile, Angie ends her relationship with Paulie. His father Lou (Anthony Quinn) finds Paulie in the bathroom and consoles him. When Angie returns home, a livid Mike violently beats her for dating a black man and throws her out of the house. Flipper and Angie move in to an apartment together, where they subsequently encounter social problems including a failed dinner with Flipper's parents, and another problem when they are walking down the street, they joke around and Flipper forces himself onto her, the police show up thinking he is raping her, she tells them that he is her boyfriend and threatens to have their badges. Flipper yells at her and does not want anyone else to know. Paulie attempts to start a similar relationship with an African American woman called Orin Goode (Tyra Ferrell), but encounters problems of his own.
Lucinda has Flipper come over and informs him that Gator has taken the television. She wants him to try and get it back before the Good Reverend Doctor comes home, so Flipper goes out to find Gator. Flipper finds Gator at a crack house, where he and Vivian are smoking the drug. Gator tells Flipper that he pawned the TV to get money for the crack. Flipper slaps Vivian in the face and tells Gator that their mother is crying over him; Gator does not appear to care. Flipper tells him that he is cutting him off for good and leaves. Eventually, issues surrounding Flipper and Angie strain the relationship so much so that they break up. Orin accepts Paulie's offer to take her on a date. But when he tells his father he is going on a date with an African American, his father disowns him. On the way to meet with Orin he gets into a fight but still heads to her house. One night, Gator storms into his parents' house while the Reverend is away, demanding money from Lucinda while trashing the house. The Reverend arrives and threatens to shoot him if he does not leave. Gator refuses to leave, antagonizing his father. The Reverend tells Gator he is better off dead, and shoots him. Gator dies in his mother's arms.
Flipper attempts to reconcile with Drew. After having sex with her, Drew, still hurt, tells him it is best for him to leave. While walking down a street, Flipper passes by a prostitute who offers to perform fellatio for two dollars. Flipper, in response, hugs her and screams "No!" out to the heavens.
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