After a series of successful comedy club performances, Floyd Mooney is presented with a potential opportunity by his agent Malcolm, but he soon finds the opportunity comes with a catch. As Floyd wrestles with his convictions against the need to provide for his son Trevor, his friend Ron surprises him with what may be an even bigger opportunity. This leads to Floyd having a meeting with a well-known public figure, who makes an offer that's hard to refuse. As he weighs a potentially life changing career advancement, Floyd also finds himself attracted to his ex-girlfriend, Trevor's mom Sadie.
- After a series of successful comedy club performances, Floyd Mooney is presented with a potential opportunity by his agent Malcolm: meet with the successful Hollywood comedy director Jason Gold, who wants him for a part in a film. Unfortunately, the meeting does not go well as Gold makes a series of unintentional politically incorrect missteps and the part he wants Floyd to play would require him to wear a dress, which Floyd flatly rejects. Things go from bad to worse when Floyd, who unbeknownst to Gold is doing a bit, defends Bill Cosby and offends Gold. Later he meets with Malcolm, who is upset about Floyd's behavior and reveals that Gold is an important client at Malcolm's agency. This infuriates Floyd because he feels this information reveals that the meeting was never for his benefit. The argument ends with Floyd firing Malcolm and storming off.
Later Floyd spends the day with his son Trevor and they go to see a movie. Walking home they have a conversation about what makes a good comedy film and Floyd mentions that he prefers films like he used to watch with his deceased father, to which Trevor responds that his mom says Floyd is a comedy snob. This leads to an awkward conversation about how Floyd and Trevor's mom Sadie are not necessarily getting back together even though he sometimes "sleeps over". After getting Trevor home, Floyd discusses his recent career events with Sadie, who reveals that she already knew about them because Malcolm called her and asked her out. The idea of Sadie dating Malcolm is disturbing to Floyd, but Sadie assures him that despite it not being his business he has nothing to worry about.
The next day Floyd has lunch with his best friend Ron and critiques him on his eating habits and excess weight, warning him about the health implications but concluding that he loves him anyway, calling him a "big, fat, sexy mother****ing Budda" and encouraging him to give up his civil service job to do comedy like Floyd. Ron states that he prefers the less stressful approach of only helping Floyd with his comedy and advises Floyd not to feel bad about the missed opportunity with Gold because it is more important for Floyd to be true to himself. On their way out of the restaurant Floyd has a run-in with a man who mistakes him for the valet. Floyd loudly denounces him as a racist, but the man unapologetic-ally explains that his mistake was because of Floyd's proximity to the valet stand and not his race, awkwardly defending his love of black woman and explaining that the stereotype of valets is that they are Hispanic, not black. Floyd is stunned speechless by the sheer obliviousness of the man and expresses that to Ron, who has surreptitiously recorded the entire exchange.
The next morning Floyd is woken up early by Malcolm, who reveals that Ron's recording, which he posted to an online gossip site, has gone viral. The clueless man Floyd argued with was in fact powerful Hollywood producer Stu Beggs, who now wants to meet with Floyd and apologize in the hopes of removing the public outrage pressure he is feeling. Floyd agrees to meet with him but finds the apology isn't very apologetic, as Stu doesn't really feel he did anything wrong and blames the public pressure on a "culture of outrage". As Floyd prepares to leave, Stu explains that they can help each other anyway; Stu will force Jason Gold to give Floyd the part in his movie, which will be good for Floyd's career and family, and Stu will get the public pressure removed as he and Floyd publicly end the dispute.
Floyd reluctantly agrees to head down to Gold's film set and is introduced to the star of the film, Jamie Foxx. They discuss Floyd's unwillingness to wear a dress for the part. Foxx, who is himself wearing a skirt, explains that the dress is nothing to be ashamed of and that it is all about becoming "white famous", a point where your extreme fame supersedes your race. Floyd considers it but decides that the dress is too much and respectfully demurs. Foxx says that Floyd will simply fade into "black obscurity" and dismisses him.
Floyd returns to Sadie's house to watch an Eddie Murphy film with Trevor; when Sadie gets home from work she lightly scolds Floyd for showing Trevor an R rated movie. After Trevor goes to bed she and Floyd discuss his meeting with Jamie Foxx and whether he should take the part. Sadie encourages Floyd to take the part regardless of having to wear a dress, suggesting that the opportunity is worth more than his pride. The conversation becomes more intimate after Floyd makes Sadie laugh with his Denzel Washington impression, but is interrupted by a call from Malcolm, who explains that Foxx was impressed by Floyd's principles and is offering him a part in the film that doesn't require wearing a dress. As Floyd is talking to Malcolm a car arrives from the studio to pick him up and bring him to the set immediately. Floyd decides to take the part and gets in the car.
During the ride to the set the driver, an older black man, congratulates Floyd but warns him about the pitfalls of pressure and expectations in the white-dominated industry. He summarizes the concept as wearing a ni**er coat. Successful black stars, he tells Floyd, should be proud but remember who they are and where they came from. Floyd arrives at the studio set with somewhat mixed feelings.