- Winston Jerome
Robert plans to audition for the leading male role in Ma Dukes Finds Herself a Man, the latest play by superstar playwright, screenwriter and actor Winston Jerome. When he declares his intent to give Winston "everything I've got," Riley advises him to say "no homo," as his statement could be misinterpreted as something gay. Robert refuses.
Robert passes the audition and Winston invites him to his compound. At the compound, Winston makes a grand entrance, descending on a golden elevator while singing "It's All Right to Cross-Dress for Christ." Robert wins the part based on his willingness to be covered in flavored lotion. He accepts the part, only to learn that he must remain inside the compound, and is unable to return to his unattended grandchildren. Realizing that Winston has ensnared Robert in a cult, Huey and Riley attempt to rescue him but are unable to persuade him to leave, even though it means kissing Winston on stage.
Two weeks later, the play premieres to a packed house. Following the performance, Winston offers him the lead in the film version of Ma Dukes Finds Herself a Man but demands sexual favors in return. He realizes that Winston founded his theatrical cult for the purpose of having sex with men. As he storms out of Winston's dressing room, Robert shouts "Fuck you! Now stick that up yo' ass!" He pops his head back into the room to add, "No homo". The episode ends showing Robert and his two grandsons driving home in the car at night time with Robert's new engaged girlfriend sitting next to Robert in the front mindlessly eating chicken wings, while Riley consistently mocks Robert by constantly playing the scene in the play where Robert gets Kissed furiously by Jerome which Riley actually recorded, while constantly saying "Pause" and "Pause again Grandad" much to Robert's annoyance frustration and irritation.
- "Pause" is a phrase used in the urban community to express an air of awkwardness after a pseudo-homosexual statement is uttered. This is commonly followed by the phrase "No homo".
- Uncle Ruckus does not appear in this episode.
- This episode along with The Story of Jimmy Rebel have been banned from Adult Swim and Hulu. The episode returned for an airing on May 29, 2020 on Adult Swim and the episode is on HBO Max.
- When the episode first aired on Adult Swim, it was rated TV-MA. But when it aired on May 29, 2020, it was re-rated TV-MA-LS. The reason behind this is currently unknown.
The similarities between Winston Jerome/Ma Dukes and Tyler Perry/Madea as well as the former's portrayal towards the end of the episode has been directed to Tyler Perry via his website, e-mails and his Facebook and Twitter pages for comment. Fans of Tyler Perry have brought the episode to Mr. Perry's attention hoping for comment and in some instances, urging him to sue Aaron McGruder and Cartoon Network. Tyler Perry addressed the controversy and at the same time put to rest rumors someone was fired after the episode aired Article at Shadow And Act. In the article he states he has no plans to sue Aaron McGruder and The Boondocks (likely in referral to Turner Broadcasting, which owns Cartoon Network and TBS, which airs 3 of Perry's shows) though some readers are skeptical as to whether this is really true. Although Tyler Perry is very familiar with McGruder's work (and obviously vice versa for Aaron with Tyler's work), those who are skeptical of Tyler's statement believe it maybe be a placeholder to an actual pending complaint filed against McGruder.
The Boondocks creator himself is of course known for controversy. He has a real-life feud with BET, openly criticized George W. Bush and even (reportedly) dissed Condoleezza Rice at the 2002 NAACP awards. He is considered an "outcast" by the American Black Power Establishment because of his leftist views and shocked many when he visited Cuba in 2003 and met with then-president Fidel Castro. One possible end result of this little facade is both men using the attention to promote their respective shows, movies/plays (Perry) and Comic Strips (McGruder), though this is unlikely since The Boondocks comic strip was cancelled in 2006, four years prior to this episode
- The character Winston Jerome is, as mentioned above, a parody of playwright and filmmaker Tyler Perry. Jerome's character Ma Dukes (who he crossdresses to portray) and the play at the beginning are parodies of Tyler Perry's character Mabel Simmons—known as Madea—and his plays and films.
- The episode parodies The Rocky Horror Picture Show and the songs "Sweet Transvestite" and "The Time Warp".
- When Granddad recalls his acting career a flashback shows him auditioning for In the Heat of the Night, Enter the Dragon, and Rocky III.
- The” brown skinned bald dude from Law and Order ” is a reference to Steve Harris who plays as one of the antagonists in the film production of Diary of a Mad Black Woman.
- The blonde-haired overweight black woman (a parody of Cassi Davis: an actress that is frequently cast in Tyler Perry's theatrical productions, as well as the television series: Tyler Perry's House of Payne ) seen through-out the episode in a zombie-like trance, states on two occasions that she “is going to get some Kool-Aid”. This is a reference to the mass suicide executed by the 909 members of The Peoples Temple Church led by Jim Jones. They all died by consuming cyanide-laced grape Flavor Aid. (The term "drinking the Kool-Aid" originates from this incident.)