Once Ned and Homer's bounty hunting partnership takes a turn for the worse, Homer becomes the hunted, as Ned is on the prowl for him after he skips bail. Meanwhile, Marge mistakenly takes a job at an erotic bakery.
While trying to earn money at the country club, Bart acquires Denis Leary's cell phone after Leary angrily chucks it away. Bart keeps the phone and makes prank calls pretending to be Leary and when Marge finds out what Bart is doing she contacts Leary. Denis says Bart might as well keep the phone, but he advises her to activate the GPS system in the phone so she can track Bart's every move.
Bart meets his doppelganger, Simon Woosterfield, a member of the richest family in Springfield and the two decide to switch places. Simon adjusts nicely to his new digs at the Simpson home, while Bart discovers that his new siblings are plotting his death so they can have his inheritance.
Parodies of It's the Great Pumpkin, Charlie Brown, Michael Bay's Transformers and on Election Day a renegade electronic voting machine turns Homer's vote into one for the other guy.
The Simpson clan takes a road trip to a cabin in the woods that Homer and Marge once vacationed at 20 years ago. In a series of flashbacks Homer and Marge reflect on some history from their courtship and Bart and Lisa recall some pleasant memories from their very early days.
Lisa discovers she has an impressive knack for solving crossword puzzles and she enters in a city-wide crossword tournament. Feelings are hurt though when Homer bets against Lisa in the championship match.
Homer suspects Bart's new friend, Bashir, of involvement with a terrorist plot to destroy the Springfield Mall.
Mr. Burns wins a professional basketball team in a poker game at the annual billionaire's retreat. In an effort to lure fans he decides to build a state-of-the-art facility, but the stadium site is on the last remaining bee colony in Springfield and Lisa leads the charge to block Burns' building.
Lisa and her new friend, Juliet, create a fantasy world that gives them a break from reality.
Homer wonders if fate truly did deal him a tough hand after he finds out that the class presidential election he lost in high school was rigged.
Bart learns that he and a few other students at Springfield Elementary have aced the Vice President's Assesment practice test, exempting them from the real exam and they are flown via helicopter to a pizza party that, instead, turns out to be something else entirely. Meanwhile, Homer's health insurance lapses when he forgets to make a payment and it makes for a harrowing day of accident avoidance as he tries to get his check to the insurance company without injuring himself.
When the adjustable rate on Homer and Marge's mortgage resets at more than they can afford, they must put their home up for sale. Good Samaritan Ned Flanders buys the house and rents it out to them at an affordable rate. But Homer pushes his luck too far when he takes advantage of Ned's generous land lording duties.
Lisa infiltrates a convent in order to steal back Maggie who was accidentally taken in by nuns. While in the convent, Lisa uncovers a series of cryptic clues leading to a hidden jewel in Springfield. With help from resident history buffs Principal Skinner and Comic Book Guy, Lisa sets off to find the coveted prize. But Springfield's Freemasons are also hot on the trail of the jewel, and Lisa must race against them to find the jewel and rescue Maggie.
The Simpsons travel to Ireland so that Grampa can have a final drink at O'Flanagan's Pub, an old watering hole of his. But when the small town of Dunkilderry isn't quite what Grampa remembers it as and O'Flanagans has become a rundown, empty pub, he and Homer decide to buy it and fix it up.
After Marge and Homer's marriage turns out to be invalid, they decide to re-do their vows. But when Homer goes missing, Bart and Lisa smell something funny and investigate his disappearance.
Moe develops an internet relationship with a woman named Maya; when the two agree to meet face to face Moe is shocked to discover that Maya is three feet tall.
Bart resorts to being a good Samaritan to win the affections of a 5th grade girl named Jenny.
Homer takes an overbearing approach to parenting Bart and Lisa with disastrous results. Meanwhile Marge takes a liking to the new sauna she discovers in the basement.
When Springfield Elementary is rated the worst school in the state Marge and Homer rent an apartment in the well-to-do Waverly Hills school district so their kids have a shot at a better education. In order to impress the other students, Bart quickly establishes a new bad boy image and helps boost Lisa's popularity by telling everyone she and pop star Alaska Nebraska are best friends. Meanwhile, Homer enjoys the bachelor lifestyle in the new Waverly Hills apartment.
Another "trilogy" episode featuring Simpsonized versions of Macbeth, The Fountainhead, Citizen Kane, and Queen Elizabeth I.
Ogdenville's economy takes a stumble after tainted barley is discovered in Krusty's veggie burgers and the unemployed of Ogdenville flock to Springfield. When Mayor Quimby closes off the town's borders and enlists private citizens to help patrol them, Homer puts together a border patrol group.