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Brown Sugar starts out with a voice-over narration from Sidney Shaw (Sanaa Lathan), a hip-hop journalist who has begun each interview for the past ten years with the same question: When did you fall in love with hip-hop? We get answers to this question from hip-hop stars artists such as Russell Simmons, Method Man, Common, Jermaine Dupri, and De La Soul.
Sidney's voice-over turns out to be part of the book she is writing about her lifelong love affair with hip-hop. It turns out that Sid fell in love with hip-hop in 1984 when she was ten-years-old and heard future stars rapping on the street. That's also the day she meets Dre Ellis (Taye Diggs), who also fell in love with hip-hop that day and is now an executive at Millennium Records.
Sid is packing up her office at the Los Angeles Times to return to New York to be the editor of an influential hip-hop magazine. Dre calls her from New York (where he lives) to get a first-look at a review of one of Millennium's new artists. He is pleased to hear that the review will be a good one. They are both happy that Sid is returning home to New York. Dre asks if she is going to be at Russell's (Simmons) party and she says yes.
Sid attends the party with her cousin, Francine (Queen Latifah), who seems to be the only one who sees the truth . . . that Sid and Dre are in love. Sid is about to order a drink at the bar when Dre walks up and orders for her. She, in turn, orders his drink for him. They hug and are very happy to see each other. Dre introduces Sid to Reese Wiggins (Nicole Ari Parker), a lawyer, and confesses that he is going to propose to her that night. Sid makes sure that he is sure and Dre pops the question.
Dre drags Sid along to a club to check out a new artist he wants to sign, however, the artist, Chris (Mos Def), manages to brush him off because he feels Millennium is not about real hip-hop. Dre then meets Millennium's newest artists, Ren and Ten (Eric Weiner & Reggi Wyns), an annoying duo and just the kind of artists Dre and Sid are avoiding. Dre confronts his boss, Simon (Wendell Pierce), about the future of hip-hop and Simon points out that they are in a business to make money. Dre almost quits, but swallows his pride.
The night before his wedding, Dre and Sid kiss. The next day, Dre marries Reese, even though Francine is pushing Sid to tell him the truth about her feelings for him throughout the ceremony.
Time passes and we see Dre and Reese's married life is pretty good. Sid gets talked into doing an interview with an elusive basketball player, Kelby (Boris Kodjoe). They meet at a restaurant, where Dre, Reese, Ren, and Ten show up as well. Kelby thinks Dre is Sid's ex, but she sets him straight.
Dre goes into the studio with Ren and Ten, who are remaking a song he considers a classic. He cannot stand his job anymore and quits on the spot. He gets into a cab outside the studio and his driver turns out to be Chris, the artist he wanted to sign. They lament over the sad state of hip-hop until Chris offends Dre and he gets out of the cab.
Dre goes to Sid, who has just received a huge delivery of flowers from Kelby, who wants to take her on a date.
Dre tells Sid that he wants to start his own label, but doesn't know where he is going to get more money. Without him even asking, Sid writes Dre a check. He goes home that night and tells Reese his plans, but she is completely unsupportive. Their marriage becomes strained after that, especially when she learns that he told Sid his plans first.
Sid goes on a date with Kelby. He closes down a popular restaurant on their busiest night and cooks for Sid himself. They are at her place and she is making coffee when Dre calls. He is whispering so as not to wake Reese. Reese comes into the room, hears him whispering to Sid, and storms out. Sid and Kelby are drinking their coffee in awkward silence. Finally, Sid suggests that they have sex and he agrees.
Dre approaches Chris one more time and he finally agrees to sign with Dre.
Reese attends the same kickboxing class as Sid and they fight about Sid's close relationship with Dre.
At Sid's New Year's party, Dre makes a speech thanking only Sid for her support of him. This clearly makes Reese mad, but she hides it well. Kelby then proposes to Sid, who says yes. Chris flirts uneasily with Francine. Dre confronts Sid about her decision and she tells him to be more concerned about his own marriage, as she has seen Reese doing some flirting at the gym. Kelby, a wannabe rapper, asks Chris to be his mentor. He also asks Reese, who wants to be his lawyer once he makes his album, how she deals with Dre and Sid's relationship. She says it's hard.
Sid finds out that Kelby has only read the article she wrote about him and is angry. He promises to read all of her articles for the rest of his life if she forgives him, which she does. Sid visits Dre and Chris at the studio. Dre's phone rings. The phone is actually Reese's. They have the same one and accidentally switch them sometimes. Turns out she is having dinner with a guy named Richard, who doesn't know she's married. Dre drags Sid along with him to confront and embarrass Reese at dinner.
That night, Dre and Sid have sex, but all does not go well.
She thanks him for the best 5 minutes of her life and sends him on his way because she has to meet Kelby.
Dre and Chris go to a radio station to get Chris' single, "Brown Sugar" (also the name of the record company), on the air. Chris tells him not to punk out with the station the way he did with Sid and the way Humphrey Bogart did with Ingrid Bergman in Casablanca. The station's boss barely gives him the time of day, so Dre leaves.
Sid goes to Dre's hotel room to confront him about Chris' single, which she is supposed to review, but turned it over to another writer, who gave it a fine, but not great, review. They almost kiss again, but she walks out.
Sid breaks up with Kelby.
Dre meets Reese at a bar, where they finally decide to end their marriage. On their way out, Sid sees them looking happy, assumes they're back together, and flees.
Dre finally goes to the radio station boss and promises to return every week until he hears Chris' song on the radio.
Dre and Chris are waiting to hear his song on the radio, when they hear Sid, who the station has been trying to interview on-air for a while. She talks about her book, which she finally finished and calls her love letter to hip-hop. She dedicates hers and Dre's song to hip-hop, who she loved, loves, and will always love. Hip-hop has been a metaphor for hers and Dre's entire relationship. He calls the station and asks her when she fell in love with hip-hop. She reminds him about the rappers on the street, but he asks the question again. She gets it and answers that she has loved him since she was ten. By this time, he is speeding to the radio station while talking to her on his cell phone. He gets into the studio and tells her he has been in love with her all his life. He holds up a sign that asks her to go out with him, with a box to check yes, no, or maybe. She says yes and they kiss. Francine asks Chris out and "Brown Sugar" is played on the air.
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