During an episode of The Krusty the Clown Show, three Itchy & Scratchy cartoons are shown. This angers Krusty, the host of the show, since he thinks he should be the star of the show and not the Itchy and Scratchy characters. Meanwhile, the Simpsons visit a television museum that is soon to be closed. After a while, they come to an exhibit displaying The Adventures of Fatso Flanagan, which is one of Homer's favorite television shows. There, the family is approached by Annie Dubinsky, the agent of the actor who played Fatso Flanagan. They start chatting and become acquainted. At the Channel 6 studios, during a board meeting, Krusty is fired because "Today's children are uncomfortable with a clown whose every reference they have to look up on Wikipedia", and because Itchy and Scratchy are shown to be more popular with the children. Krusty goes to his current agent, hoping to get a new job, but the agent drops him since he got fired.
After the Simpsons have left the museum, they head for Krusty Burger where they discover Krusty crying in a ball pit. Krusty is encouraged by them into making a comeback, and they inform him that they met an agent that can help him out. However, when they all go to Annie's office, Annie instantly recognizes Krusty and angrily slams the door before he gets a chance to enter. It is revealed that Annie was the one who discovered Krusty, became his first agent, and was responsible for his rise to success. They also had a romantic relationship together. However, once he achieved fame, Krusty fired Annie and replaced her with a more acclaimed agent, and as a result their relationship ended. Back in the present, he begs her to take him back as a client, and she eventually accepts.
Krusty starts performing his clown tricks at a theater in front of adults, and not children like before. This is because Annie knows that there is nothing adults enjoy more than the things they liked as children. The performances are praised by both the audience and the critics, and Krusty and Annie initiate a relationship again. Soon, a premium cable television network called HBOWTIME (an obvious portmanteau of HBO and Showtime, straight down to their parody of HBO's longtime slogan, "It's not just TV, it's more expensive.") gives Krusty his own show and Annie is hired as the producer on his demand. The stars of the series Entourage, such as Kevin Dillon, become Krusty's assistants. The network executives soon become frustrated with Annie for meddling too much in the show. For example, she refuses to let Janeane Garofalo appear only because Garofalo is funnier than Krusty. She also runs over an intern with a stage car for sharpening her pencil too much. The executives decide to fire Annie, but Krusty refuses to continue without her. The couple therefore turns to another network where they start a show called Sex Over Sixty, with them as the stars.