Mr. Burns discovers that his employees do not like him very much, because of his pompous ways. Smithers decides to helps a distraught Mr. Burns go undercover as a man named Fred Kranepool. Initially determined to punish disloyal employees, the plant employees grow to like "Fred", causing Mr. Burns to want to adopt that personality permanently. Smithers is forced to expose his boss, causing Mr. Burns to revert to his former tyrannical personality.

Guest stars: David Harbour as Mr. Burns' undercover persona Fred Kranepool and Philip Rosenthal as himself

While the Simpson family visit a museum exhibit on Ancient Rome, Marge chastises a bored Homer for his lack of ambition when he admits to shirking chances for promotion. The curator overhears the squabble and begins to relay the tale of Obeseus the Wide (Homer), a gladiator who went on to become a powerful Roman senator, only to be usurped by his own son (Bart).

Guest stars: Joe Mantegna as Gordus Antonius (Fat Tony) and Michael Palin as the Curator

While sick, Lisa reads a book about Western art, and imagines her family as famous painters.

• "Lisanardo da Vinci": Lisa imagines herself as Leonardo da Vinci, the painter and inventor.

• "1863 France": After initially being picked on by the other students, a French impressionist (Bart) receives praise from a stranger for his work and he earns the respect of the other students.

• "Cupid": Cupid (Maggie) shoots Homer with an arrow and he dies, descending into a Hieronymus Bosch hell.

• "Frida Kahlo": Shortly after Diego Rivera (Homer) and Frida (Marge) are married, Diego has them move to America, where John D. Rockefeller has Diego paint a mural at the Rockefeller Center, while Frida is left out, causing friction in their marriage.

A Treehouse of Horror episode that consists of four segments, a short intro based on the 2020 United States presidential election and the three usual main segments.

• "2020 Election": During Election Day 2020, everyone is voting who will be the next president of the United States, except for Homer who does not vote. 2 months later, on Inauguration Day 2021, the entire city of Springfield is in chaos, while Homer relaxes.

• "Toy Gory": Bart is gored by his own toys as revenge for treating them so badly.

• "Into the Homerverse": Homer accidentally mistakes a machine at the nuclear plant for a vending machine and when he inserts a coin into it, multiple different versions of himself from different dimensions come through a portal.

• "Be Nine, Rewind": Lisa gets stuck in a time loop on her ninth birthday in which she dies each time.

Guest star: Ben Mankiewicz as himself

A beautiful English woman named Lily comes to Springfield and becomes enamored with Homer as the rest of the family vacations in New England.

Guest stars: Olivia Colman as Lily, Robin Atkin Downes and Brian George as Various Englishmen

When Marge and Lisa get addicted to true-crime podcasts, they feel like the experts when Grampa is accused of murdering his new girlfriend Vivienne. At the same time, Kent Brockman makes a podcast of his own about the occurrence entitled "Guilty Grampa".

Guest stars: Morgan Fairchild as Vivienne St. Charmaine, Christine Nangle as Tabitha Shingle and Stellan Skarsgård as himself

Note: This episode was dedicated in memory of Alex Trebek who previously guest starred as himself in the episodes "Miracle on Evergreen Terrace" and "Penny-Wiseguys." Regular cast member Yeardley Smith also appears in a cameo as herself (the host of the podcast Small Town Dicks).

Comic Book Guy attends the Comicalooza convention, planning to present the ultimate audience question with hopes he will be hired by Marvel Comics. Meanwhile, Lisa develops a crush on a new kid named Blake who also plays the saxophone but isn't what he seems. Bart is hired as a voice-over actor for a new cartoon show, only to become embarrassed by the role where he has been cast as a princess.

Guest stars: Ben Platt as Blake and Paul Rudd as himself

When Superintendent Chalmers is selected to give the keynote speech at an administrator's convention in Cincinnati, Principal Skinner takes some advice from Bart and replaces favored Principal Finch as his superior's plus-one, hoping he can get to know Chalmers better during their 800-mile journey to get there.

Guest stars: Jason Bateman as himself and Hannibal Buress as Principal Finch

When Lisa's "Who Inspires You?" project results in the same B− grade as every other student in her class, she becomes angered with Miss Hoover and calls her a hack. When Lisa refuses to apologize she is sent to detention. When her stubbornness only makes matters worse, she is encouraged to try and understand things from her teacher's point of view.

Guest stars: Christine Nangle as Ms. Timberwood, Ariana Piknjac and Ella Piknjac performing the end titles theme

Aspiring Heartmark Channel film producer Mary Tannenbaum is sent to Springfield to help sort out problems with a Christmas movie being filmed there during Summer. Mary stays with the Simpsons where Heartmark fan Marge assertively tries to befriend her, Homer tries to profit from the film, Lisa follows Mary with her own camera to film a behind-the-scenes documentary and Bart becomes bitter when he has to give up his room for film crew. Meanwhile, Mary forms an odd rapport with Seymour Skinner after the two make a deal so that her film doesn't interfere with his Lettuce and Tomato Festival.

Guest stars: Ellie Kemper as Mary Tannenbaum, Richard Kind as the director and Chris Parnell as Mary Tannenbaum's fiancé

Homer and Marge team up with Comic Book Guy and his wife Kumiko to win a trivia contest. After spending time with Maggie, Kumiko decides she wants to have a baby, only for her husband to disagree. But just as Comic Book Guy begins to come around on the matter, the pressure to offer emotional support to a distressed Bart and Lisa sees him fleeing his wife and problems back to his family home.

Guest stars: Dan Aykroyd as Postage Stamp Fellow and Bob Balaban as the narrator

Bart and Milhouse discover Mrs. Krabappel's old diary after buying a bunch of books at Ned Flanders's yard sale to attempt a stunt. Discovering a page where Krabappel had written her success of fixing Bart's school life after classes, Bart is suddenly convinced that he's the most improved student. With the help of Maggie, Lisa finds the diary at the treehouse and discovers that Mrs. Krabappel was actually referring to her cat, but only reveals this to Bart after he decides to enter the school's spelling bee. Later in the treehouse, Ned tells Bart that Mrs. Krabappel surely still thought fondly of him, and a thankful Bart returns the diary to him.

Guest stars: Marcia Wallace as Edna Krabappel (archive recordings) and Joe Mantegna as Fat Tony

After being told of a golf course in Springfield where golfers pay their caddies very handsomely, Bart signs up for the job. Marge goes to great limits to encourage Bart to quit after worrying about his personality and future. After Marge accidentally causes the sport to become a religion, Bart is finally convinced to leave his job and attempts to destroy the golf course.

Guest stars: Stephen Root as Bildorf and James Sie as The Lama

Note: This episode was dedicated in memory of Marc Wilmore, a writer and producer of The Simpsons who died on January 30, 2021.

When Homer spends a night sharing the drunk tank with Cletus, the yokel's singing about family makes Homer remorseful and he vows to become a better husband and father. Homer offers to manage Cletus to help him become a country singing sensation, only for success to see Cletus replacing Homer with a new slick manager when he decides to go professional.

Guest star: Albert Brooks as Slick manager

A pizza palace visit awakens bad memories of Homer's youth working there, when the mechanical band he loved was taken from him. Marge, Bart, Lisa and Moe all track down the lost animatronics to reunite them for Homer once again, but discover that film and television producer J. J. Abrams is also collecting the band for his next film project.

Guest stars: J. J. Abrams as himself and Greg Grunberg as Bad Robot Head of Security

Note: This episode is dedicated in memory of David Richardson, a writer and producer of The Simpsons who died on January 18, 2021.

During Christmas, Bart finds an ornament featuring Todd Flanders on it, prompting Homer and Marge to proceed telling the kids a flashback event from 6 years prior about the Flanders family's past and a secret room within the Simpson household.

• This is the show's 700th episode.

While on a chaperone trip with Bart's class, Marge finds out that Ralph Wiggum's mother Sarah actually has more to her personality on the inside than on the outside. When she and Sarah are captured by the latter's old partners-in-crime, they reveal the secret about Sarah's past to Marge and recruit them to take part in a jewel heist.

Guest stars: Joe Mantegna as Fat Tony, Megan Mullally as Sarah Wiggum, Nick Offerman as Captain Bowditch, Natasha Rothwell as Bette, Bob Seger as himself and Tiya Sircar as Erin

Mr. Burns almost kills himself eating Krusty Burgers and learns that the town would prefer he had died. To help his boss with both his image and newfound love of burgers, Smithers suggests Burns get into the plant-based burger business. Soon Burns has both Lisa and Homer aboard, while Marge accidentally buys ever-rising stock in Burns' new company. But when Bart sees Krusty Burger failing and tries to get Lisa to help, she does not believe that Burns' new venture is evil.

After being humiliated in front of the whole school when she accidentally eats bacon, Lisa begins hallucinating depressed 1980s British singer Quilloughby as an imaginary friend who helps her fire back at the mean people around her. Meanwhile, Homer becomes obsessed with a new truck with awesome torque.

Guest star: Benedict Cumberbatch as Quilloughby^[26]

Note: This episode was dedicated in memory of Edwin E. Aguilar, an animator, character layout and assistant director of The Simpsons who died on April 11, 2021.

At a magic store, the family is given tarot card readings that tell of another future disagreement between Lisa and Marge. In this case, it involves Lisa deciding she doesn't want to go college and both declining her many great admission offers and completely devastating Marge in the process. Lisa then finds her own path of education that leads to her becoming President of the United States, but it'll be a harder task to mend fences with an enduringly-bitter Marge.

Guest stars: Werner Herzog as The Amazing Herzog, Nate Silver as himself and George Stephanopoulos as himself

Note: This episode was dedicated in memory of Olympia Dukakis who previously guest starred as Zelda in the episode "The Old Man and the Key".

Homer meets a British secret agent named Terrance who has spent 50 years hunting a suspected Russian spy known as "The Grey Fox". After Homer and his friends hear Terrance's story, Homer soon discovers that not only is Grampa Simpson the man Terrance seeks, but that he might even be a traitor like the agent claims.

Guest stars: Stephen Fry as Terrance, Head of MI5, Terrance's Father and Hazel, Robin Atkin Downes and Brian George as MI5 Agents, Maurice LaMarche as Orson Welles and Dima Malanitchev as Russian See 'n Say

After Moe breaks their one important rule, a secret society of bartenders seeks ultimate vengeance on Homer and his drinking buddies. This causes Homer's friends and himself to be hunted down by all the bartenders in Springfield. The bartenders inject them with "Anti-Booze", a serum that stops them from drinking alcohol.

Guest stars: Ian McShane as Artemis and Cesar Mazariegos as Grampa Baby