Homer is sent to jail after a brawl at the St. Patrick's Day Parade; after getting bailed, he meets Lucky Jim and Wolf the bounty hunter who prompt him to try his own hand at bounty hunting with Ned Flanders. Homer's new attitude gets the best of him, and Flanders is not impressed. Meanwhile, Marge begins working at an erotic bakery. Guest stars: Julia Louis-Dreyfus, Robert Forster and Joe Mantegna.
Bart manages to get Denis Leary's own cell phone and uses it for prank calls while posing as Leary. Marge discovers Bart's tricks and informs Leary of what Bart has been doing. Leary suggests Marge put a GPS in the phone, but Bart discovers it and sends his family on a chase that ends in Machu Picchu. Guest stars: Denis Leary and Brian Grazer.
Bart meets Simon Woosterfield, his exact look-alike who is a member of the richest family in Springfield. Simon and Bart decide to switch places, though Mr. Burns quickly informs Bart that his new siblings are plotting his death in order to inherit the vast Woosterfield family fortune all for themselves. Guest star: Joe Montana.
Intro: Homer tries to vote for presidential nominee Barack Obama but the machine is rigged to place votes only for John McCain. After he discovers that the machine is rigged it pulls him in and kills him.
Untitled Robot Parody: In a parody of Transformers, the Autobots and Decepticons wage war with one another, obliterating Springfield, until Marge asks them why: as they can't remember, they team up and conquer the human race.
How to Get Ahead in Dead-Vertising:After accidentally killing Krusty, Homer discovers that dead celebrities can be put in commercials for free, so he starts killing celebrities. The angry spirits of the dead celebrities return to Earth to battle Homer.
It's the Grand Pumpkin, Milhouse: In a parody of It's the Great Pumpkin, Charlie Brown, the Grand Pumpkin comes to life and becomes upset with human beings carving up pumpkins, so it tries to eat everyone.
The Simpson family visits a cabin in the woods where a series of flashbacks depict Homer and Marge during their dating and early married years. When Homer and Marge realize that one of their most cherished moments was based on a pile of lies, the two attempt to work out their issues. Guest star: Maurice LaMarche.
Lisa discovers she has a talent for crossword puzzles and enters a tournament. Homer discovers the world of underground betting ring and bets against Lisa in the championship match. When Lisa finds out, Homer tries to regain her love with help from New York Times editor Will Shortz and crossword puzzle inventor Merl Reagle. Guest stars: Will Shortz, Merl Reagle and Scott Thompson.
Bart befriends a Muslim boy named Bashir. Homer, however, suspects his parents are plotting to destroy the Springfield Mall so he tries to warn Springfield of the impending doom. Meanwhile, Lisa gets a "Mypod". Guest star: Shohreh Aghdashloo.
Mr. Burns wins a basketball team in a poker game. After witnessing the antics of Mark Cuban at a game, Burns attempts similar things to win over Springfield basketball fans. These antics fail, and Burns' plan to build a new sports arena endangers a bee colony under the care of Lisa, who starts a campaign to save the bees. Homer tries to help by mating the bees with "killer" African bees. Guest stars: Mark Cuban, Jeff Bezos and Marv Albert.
A man named Vance Connor is inducted into the Springfield Walk of Fame and Homer recounts how he ran against Vance for class president in high school and lost. A cook at Luigi's Restaurant uses his magical tomato sauce to help Homer see what his life would have been like had he won the election.
Bart receives a perfect score on a practice test for the upcoming Vice President's Assessment Test. Because of this, he will not have to take the real exam and will get to attend a special pizza party. Lisa, shocked that Bart did better, is unable to do well on her exam, but Bart realizes that the party is not what it seems. Meanwhile, Homer is late making an insurance payment and must go an afternoon without injuring himself.
Homer and Marge's mortgage rate rises and they are forced to sell their house. Flanders buys the property and becomes their new landlord. Homer accuses him of neglecting their unsafe living conditions and Flanders threatens to throw them out. Guest star: Maurice LaMarche.
Homer leaves Maggie on the doorstep of a convent and the nuns take her in. Lisa tries to infiltrate the convent and rescue Maggie and discovers a series of messages that could lead her to a coveted jewel. She gets help from Principal Skinner and Comic Book Guy, but the Freemasons, led by Mr Burns discover her plans and try to get the jewel first. Guest star: Ed Begley, Jr.
Homer neglects Grampa by not joining him in a three-legged race. To make up for it, he agrees to take Grampa to O'Flanagan’s pub in Ireland where Grampa claims he had the best night of his life. They discover that pubs are no longer popular there and end up buying it after a night of drinking. Guest stars: Colm Meaney, Glen Hansard and Markéta Irglová.
When Homer and Marge's marriage turns out to be invalid, Homer asks Marge to marry him again. But after Homer mysteriously disappears on their wedding day, Bart and Lisa search for clues and believe Sideshow Bob could be the culprit. Meanwhile, Homer is locked in an underground bathroom and forced to lick a lollipop made of hot sauce in order to escape.
Moe falls in love with a woman over the Internet. When he meets her in person, she turns out to be three feet tall. He remains in love with her, but worries about what his friends will think. Meanwhile, Homer attempts to spend more time with Maggie.
Bart falls in love with a charitable girl named Jenny, prompting Bart to behave in order to date her. However, she discovers his true personality, causing him to end up reverting back to his old ways. Meanwhile, Lisa becomes depressed over Springfield's future while doing a school report on what the town will be like in 50 years. Guest star: Anne Hathaway.
When Marge learns Springfield Elementary is the worst school in the state, she and Homer rent an apartment in the upscale Waverly Hills school district so Bart and Lisa can attend a better school. Meanwhile, Homer moves into the rented Waverly Hills apartment and gets used to the bachelor lifestyle. Guest stars: Ellen Page and Maurice LaMarche.
Marge and Lisa visit the nail salon where they engage in a spirited debate as to whether a woman can be smart, powerful and beautiful all at the same time and spin four tales of famous women featuring famous Springfield faces: Selma as Queen Elizabeth I, Lisa as Snow White, Marge as Lady Macbeth and Maggie as the idealistic architect protagonist from Ayn Rand’s The Fountainhead. Guest star: Jodie Foster.
When Ogdenville’s economy crumbles due to tainted barley discovered in Krusty’s veggie burgers, the unemployed workers of Ogdenville flock to Springfield. After Mayor Quimby closes Springfield’s borders and enlists private citizens to help patrol them, Homer organizes a border patrol group.