Dre Ellis (TAYE DIGGS) and Sidney Shaw (SANAA LATHAN) have known each other since they met as young kids. Having grown up along with hip-hop music, the two are still in the business. Dre is a producer for Millennium Records where he's grown uncomfortable with rampant commercialism on the part of his boss, Simon (WENDELL PIERCE), in signing goofy acts such as Ren and Ten (ERIK WEINER & REGGI WYNS), the Rap Dalmatians, in an effort to sell records.
Sidney is a respected music journalist who's also writing a book on her love of and involvement in the hip-hop scene. Although the two friends are so close they practically know everything there is to know about each other, they're blind to any sort of possible romantic attraction, although Sidney's best friend, Francine (QUEEN LATIFAH), can easily see it.
Nevertheless, Dre ends up marrying Reese (NICOLE ARI PARKER), a lawyer, while Sidney starts dating
Kelby Dawson (BORIS KODJOE), a professional basketball player. Despite their involvement with them, Dre and Sidney still spend a great deal of time together. Not surprisingly, their closeness progressively irritates and worries their significant others, particularly when Sidney decides to help bankroll Dre's new business of signing real artists such as Chris (MOS DEF), a cab driver who's initially reluctant to sign anything.
He eventually does, and as times passes, Dre and Sidney, as well as their significant others, eventually come to realize what Francine has known all along, and that's that the two belong together.