<P> Jimmy's friendship with Wink (Eugene Byrd), a radio DJ with ties to a record label prompter, becomes strained after he discovers that Wink does promotional work for Jimmy's rivals, a rap group known as the "Leaders of the Free World". At one point, Jimmy and his friends get into a violent brawl with the Leaders, which is disrupted when Jimmy's friend "Cheddar Bob" pulls out a gun and accidentally shoots himself in the leg; he survives, but is confined to crutches . </P> <P> At work one day when on lunch break, Jimmy witnesses a rap battle in which an employee named Mike (Xzibit) insults a gay co-worker named Paul with his lyrics . Jimmy joins the battle to defend Paul by berating Mike . Alex is impressed by his actions, and she and Jimmy have unprotected sex in the factory . Wink arranges for Jimmy to meet with producers at a recording studio, but Jimmy finds Wink and Alex having sex atop a mixing console . Enraged, Jimmy beats up Wink as Alex tries to break it up . In retaliation, Wink and the Leaders of the Free World attack Jimmy outside his mother's trailer . The leader of the gang, Papa Doc (Anthony Mackie), holds Jimmy at gunpoint, threatening to kill him but Wink dissuades Papa Doc . </P> <P> Jimmy's best friend Future (Mekhi Phifer) pushes him to get his revenge by competing against the Leaders of the Free World at the next rap battle . However Jimmy's late - night shift conflicts with the timing of the next battle tournament . But a goodbye visit from Alex, who is moving to New York, changes his mind about competing . Paul, the work colleague whom Jimmy had stood up for earlier, agrees to cover his shift at work as a thank you, and Jimmy goes to the battle . </P> <P> In each of the three rounds of the battle, Jimmy is pitted against a different member of the Leaders and wins the first two rounds . In the final round he is paired against Papa Doc . Jimmy is aware that Doc knows all his flaws, so he uses his difficult life as a springboard to reveal the truth about Papa Doc: his real name is Clarence and despite passing himself off as a thug he comes from an affluent background, having attended Cranbrook Schools, a private high school in upper - class suburb Bloomfield Hills, and grown up in a stable, married two - parent household . </P>

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