Waymon has a great job in real estate and a promising future, but he\'s also trapped in a loveless longterm relationship. He meets Natalie, a beautiful club-hopping hipster, and quickly falls in love. Realizing he\'s just not cool enough to attract her on his own, he seeks the help of his friend Bobby, a free-spirited smooth talker who works in the mail room at Waymon\'s firm and utilizes the predicament as leverage to advance in the company.
Jack Spade returns from the army in his old ghetto neighbourhood when his brother, June Bug, dies. Jack declares war on Mr. Big, powerful local crimelord. His army is led by John Slade, his childhood idol who used to fight bad guys in the 70s.
Aspiring actor and hot-dog stand employee Bobby Taylor catches the ire of his grandmother for auditioning for a role in the regrettably titled exploitation film \"Jivetime Jimmy\'s Revenge.\" When Tinseltown Studios casts Taylor in the title role, he has a series of conflicted dreams satirizing African-American stereotypes in Hollywood, and must reconcile his career goals with his desire to remain a positive role model for his little brother.