Aspiring actor Bobby Taylor (no relation) is fueled by an unrelenting passion to break into the entertainment industry, with unwavering support from his younger brother Stevie. However, he constantly faces challenges, including his grandmother's stern disapproval of his career choice and her insistence that he consider a more respectable job, like working at the post office. Yet, his mother stands firmly by him, encouraging him to pursue his dreams. Bobby believes that landing a role in Jivetime Jimmy's Revenge, a film filled with cliched depictions of street gangs, could change their family's fortunes forever.
After his audition, Bobby gets into a heartfelt discussion with Mr. Jones, the owner of Winky Dinky Dog, where he works part-time. Jones shares his concerns about Bobby's frequent absences due to auditions and how that affects his commitment to the job. Just when Bobby is contemplating his response, a sleek limousine pulls up, and out steps B. B. Sanders (Batty Boy), a famous actor best known for his role in the hit sitcom There's a Bat in My House. Thrilled to meet a role model, Bobby inquires about how to evaluate a script's worthiness. Sanders provides a pragmatic insight: acting is about making money, focusing on sequels and merchandising rather than pure artistic expression.
After hearing from his agent that his audition went well and he has been invited to a callback, Bobby feels relieved. However, the producers' demand for an "Eddie Murphy-type" performance plunges him into a nightmare, where he finds himself being pressured by the director, writer, and casting director to transform into Eddie Murphy. As he stands in line with lookalikes, he begins to morph into the very actor he's being coerced to resemble, only to awaken in shock.
The following day, his colleagues at Winky Dinky Dog, Donald and Tiny, belittle his aspirations, prompting Bobby to resign. That evening, he seeks advice from his uncle Ray, a once-promising singer who chose stability over pursuing fame. Ray's encouragement lifts Bobby's spirits, instilling confidence in his dream to succeed.
At the callback, the director, writer, and casting director laud Bobby's performance, leading to exhilarating news that he has secured the lead role. As he reflects on his journey so far, he understands that perseverance and risk-taking have paid off.
With his newfound success, Bobby grapples with the moral implications of his current role, depicted through vivid daydreams that manifest like surreal vignettes. In one imaginative sequence titled Black Acting School, he observes white coaches instructing black actors on how to connect with their supposed cultural heritage, resulting merely in a shallow imitation. Another dream, Sneaking Into the Movies, features two young black men who effortlessly sneak past ticket takers, delivering scathing critiques of poor cinematic choices like Amadeus Meets Salieri, Chicago Jones and the Temple of Doom, Dirty Larry, and Attack of the Street Pimps.
Back at home, Bobby's excitement is dampened by a visit from his grandmother and girlfriend Lydia. The three of them sit down to watch a classic film noir, which ignites Bobby's fantasies of crafting his own cinematic vision. In one daydream, he imagines himself as the lead in Death of a Breakdancer, a compelling fusion of neo-noir with the high-energy vibe of breakdancing culture.
That night, as he dreams, Bobby envisions himself in an array of iconic roles, such as a commanding Shakespearean king, a heroic black superhero using his powers for good, and a black rendition of Rambo, bravely battling against oppression.
In a climactic dream sequence, Bobby finds himself on stage, proudly holding his fifth Oscar statuette while the crowd erupts in applause. The next day, he begins filming Jivetime Jimmy's Revenge, with his family present to witness his achievement. But as the cameras roll, feelings of guilt arise over portraying a stereotypical character, leading him to make a courageous choice—he quits the film to maintain his artistic integrity.
In the wake of Bobby's departure, another cast member who had previously criticized the project for its racial stereotypes hastily accepts Bobby's role. Undeterred, Bobby and his family leave the set with pride in their decision to uphold their values.
The film concludes with Bobby preparing for an upcoming on-camera scene, echoing his grandmother's earlier wisdom. He finds himself filming a public service announcement for the US Postal Service, symbolizing that no matter how cutthroat Hollywood can be, there is always space for kindness and humility.
