Marge is given her old production manual about her high school play, "Y2K: The Millennium Bug" and is filled with warm memories of being the stage manager. But when she's encouraged to reunite her old classmates to restage the play, old rival Sasha Reed arrives to Springfield, and Marge realizes that, due to being unseen by the audience in the backstage, Sasha was the real star of the show.

Grampa is tricked by a phone scammer into believing that he needs to bail Bart out of jail, costing him $10,000. When Homer learns that that money was intended to be his inheritance, he blames Grampa for falling for a stupid trick, while Bart and Lisa try to track the scammer down and Marge begins to think that everything in life is a con.

This is the first Treehouse of Horror episode to consist of five segments instead of the typical three. It includes the opening segment, the three main segments and a minute-long segment.

• "Barti": The opening segment, being a parody of Bambi, Marge warns Barti (Bart) and Milhouse about a hunter. Milhouse gets killed, as Barti and Marge run away. After his escape, Barti searches for his mother, who is okay, as Homer killed the hunter (Mr. Burns) with Lenny.

• "Bong Joon Ho's This Side of Parasite": A parody of the film Parasite, it starts out with a poor Simpsons family in a flood, when Bart gets a job as a tutor for a rich girl. Soon, the rest of the family has gotten jobs at the estate, supplanting the previous employees, the Van Houtens. Soon, the entire city erupts into a violent, class-driven riot, with the Simpsons as the only survivors.

• "Nightmare on Elm Tree": Homer is tired of Bart telling scary stories on Halloween in his treehouse every year, so Homer chops it down. The tree trunk is struck by lightning and comes to life. After the tree find out people chop down trees for Christmas, it brings other trees and plants to life and they ravage Springfield and kill most of its residents. The trees celebrate while the townspeople's corpses have been stacked like a Christmas tree.

• "Poetic Interlude": The minute-long segment of the episode, Vincent Price is reading a scary bedtime story to Maggie about how Bart has spent an entire year doing mischief and other bad things. He starts off with each month that Bart does something bad like having his first drink of beer, stealing the principal's car and crashing it into the school flagpole, and beheading the entire Simpson family during Thanksgiving. That is when Maggie strangles Vincent with the string to her Phonics frog and then goes to sleep.

• "Dead Ringer": In a parody of The Ring, at Springfield Elementary, Sherri and Terri tell Lisa they had a party and did not invite her, and all watched a TikTok that allegedly kills anyone who watches it after seven days. All of the children who watched it die shortly thereafter, and Lisa and Bart investigate its origin. They find out from Groundskeeper Willie that the TikTok is haunted by the ghost of Mopey Mary, a girl who did not receive any valentines on Valentine's Day and died after falling down a well. Lisa watches the TikTok and summons the ghost of Mary, who attacks Lisa but stops when Lisa gives her a valentine. Lisa and Mary become friends, but Mary begins to feel smothered by Lisa and escapes by jumping back down the well. Kang and Kodos sing at the end of this "Treehouse of Horror" episode.

Guest stars: Susan Egan as the "You'll Never Sleep Again" Singer, Maurice LaMarche as Vincent Price and Tree Rollins as himself

As Evergreen Terrace is stuck in a major traffic jam, Moe reunites with his former love Maya (from season 20's "Eeny Teeny Maya Moe"). However, Moe tries to determine himself if he should stick with Maya this time or if she will leave him again.

Lisa and Bart contract an infection from an abandoned waterpark attraction, requiring treatment from steroids that cause temporary weight gain. Before they go back to school, Marge tells Lisa that she is getting "chunky" in affection, which causes her to be very insecure about her weight. Meanwhile, Bart gets in shape with Jimbo, Nelson, Dolph, and Kearney.

A two-part crime thriller parody presented in the format of prestige television. When Ned Flanders finds a bag of money and donates it to the local orphanage, he puts himself, a jealous Homer and all of Springfield in danger, when it draws the attention of a ruthless debt collector who will get the money back by any violent means necessary.

Smithers is disheartened by Mr. Burns' lack of reciprocal feelings, so Homer encourages him to start a relationship with famous fashion designer Michael de Graaf. Michael loves that Smithers is not interested in him for his fashion ties, but what Smithers does not know is that his new boyfriend is a lot more like Mr. Burns than he initially seems.

When Mother's Day rolls around, Homer starts to miss his mother again. In order to deal with his grief he uses online therapy to reflect on his teenage years, when he and Grampa took a road trip to Utah after Homer got a secret message from his fugitive mother.

Marge decides to baptize Maggie, so she sends Homer to find an appropriate godfather for her. After Fat Tony saves Homer and Maggie's lives, Homer and Marge reluctantly agree to let the mafia don be their baby's sponsor. But the more Fat Tony bonds with Maggie and draws her into his world, the more worried her real parents become.

When Mr. Burns chooses brutally candid football prodigy Grayson Mathers to endorse his brandy and corrupts the already arrogant athlete further, Marge takes it upon herself to try and save the promising rookie by teaching him some humility and family values.

Guest stars: Beck Bennett as Grayson Mathers, John Mulaney as Warburton Parker and Adam Schefter as himself

A series of unfortunate events make it look like Homer intentionally shut Santa's Little Helper in the car on a hot day, then get worse when he accidentally knocks Reverend Lovejoy out of the church window. Videos of the incidents go viral online and everyone in Springfield turns on Homer only for a mysterious man named Theo to approach him with a radical offer to repair Homer's reputation.

Homer promises to buy Bart a pair of limited edition sneakers only to buy bootlegs instead. When Bart tries to return them, he is humiliated publicly and declares that Homer is the least cool person ever. When young shoe creator Orion Hughes feels sorry for Bart and donates his branded skate wear and merch, Bart learns that the famous kid influencer cannot actually skate himself. Meanwhile, a dejected Homer uses Orion's gifted clothing to influence other middle-aged men to dress in hip threads to prove they can be cool.

Lisa becomes enraged when a song by Bleeding Gums Murphy is remixed to promote the Springfield lottery, leading to her tracking down the late jazz musician's son. When Lisa learns that Monk Murphy was born deaf and never heard his father's music, she goes on a crusade to both improve his life and seek justice for her mentor only to discover she and Monk are not on the same page. Lisa does get advice from the Ghost of Bleeding Gums Murphy on how to get on the same page as him.

Guest stars: John Autry II as Monk Murphy, Kathy Buckley as Thespian Girl and Eli Steele as "The Sky's the Limit" Director

Bart starts acting strangely when new teacher Ms. Peyton takes over his classroom, confusing not only her but everybody around him. But what only Bart knows is that his new teacher saved his life once before. Meanwhile, Lisa breaks the prime directive of nature documentary film-making when she stops a shark from eating a small octopus. She secretly keeps her new octopus friend in her room only for it to keep escaping.

Lisa is selected as a replacement saxophonist for the high school marching band where she discovers to her surprise that Shauna Chalmers shares a similar passion for music. While Lisa and Shauna form a new bond, Homer finds himself bonding with Shauna's father when Superintendent Chalmers introduces him to the ancient craft of Trappist beer brewing.

When Marge is badmouthed in public by a former principal Ms. York, she reveals to her family that she was secretly a prankster in her middle school years. While Bart and Marge both bond over this newly unveiled connection between them, a left out Homer seeks to find some kind of common ground with Lisa. But while he discovers they both share a love for food, Homer struggles to maintain a mutual passion for Lisa's vegan tastes.

When billionaire Augustus "Gus" Redfield buys Krusty's parent company as revenge after Krusty stole his burger business years ago, he asks former business partner Grampa Simpson to join his board of directors. Grampa and Lisa go to New York where the rest of the Redfield family want to oust Gus, and his ambitious daughter Sheila tries to manipulate Lisa into getting Grampa on their side in a vote of no-confidence. Meanwhile, Krusty tries to perform without his identity.

Bart makes an embarrassing presentation about his father for Sunday school, so Marge encourages Homer to take Bart to work with him to show their son what a good provider Homer is. Bart begins to idolize Homer and wants to grow up to be just like him, but soon learns from a singing janitor that the once thriving middle class his father is part of is not in the cards for him.