Jimmy's friendship with Wink (Eugene Byrd), a radio DJ with ties to a record label promoter, 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 (Evan Jones) pulls out a gun and accidentally shoots himself in the leg; he survives but is confined to crutches.