Homer is sent to jail after a haphazard, booze-free brawl at the Springfield St. Patrick’s Day parade. When he goes to get his bail bond, Homer meets Lucky Jim (guest voice Robert Forster) and Wolf the Bounty Hunter and decides to try his own hand at the lucrative profession. The new-and-improved Homer the Bounty Hunter soon teams up with Ned Flanders to create quite the unlikely bounty-hunting duo, but when Homer’s new no-mercy attitude gets the best of him, Flanders is less than impressed. Meanwhile, unbeknownst to her, Marge begins working at an erotic bakery.

Bart gets a job at a country club retrieving golf balls so he can buy a cell phone like the rest of the kids. When Bart accidentally finds Denis Leary’s (guest-voicing as himself) cell phone, he keeps it to make prank calls and negotiate big career moves. When Leary finds out what happened, he sends Bart and the Simpson family on a wild goose chase all the way to Machu Picchu.

When Lenny wins the lottery and invites the Simpson family to a celebratory party at a posh hotel, Bart meets his doppelganger, Simon Woosterfield, who happens to be a member of the richest family in Springfield. Simon and Bart decide to switch places, and Bart arrives at the lavish Woosterfield mansion only to find football great Joe Montana hanging around the estate. As Simon adjusts to the simple life over at the Simpson household, Bart begins to notice his wealthy new siblings acting strangely toward him. With some frightening words of wisdom from Mr. Burns, Bart realizes his new siblings are plotting his demise so they can inherit the Woosterfield family fortune all for themselves. Lisa and Simon must reach Bart before he goes from riches to ditches.

How to Get Ahead in Dead-Vertising: Homer discovers that the likenesses of dead celebrities can be put in commercials for free, so he starts killing celebrities. After killing Krusty, the Clown convinces dead celebrities to stage an attack upon Homer. Untitled Robot Parody: Bart buys a Malibu Stacy convertible for Lisa from a 99 cent store, which turns out to be a Transformer. When the Autobots and Decepticons bring their conflict to Springfield, Marge asks why the robots war with one another, inspiring the two sides to team up and conquer the human race. 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 early married years while Bart and Lisa also remember times from their early childhood. One flashback takes place when a pre-married Marge and Homer first meet Ned and Maude Flanders, who insist that Homer and Marge sleep in separate beds in different room.

Lisa discovers an amazing talent for doing crossword puzzles, and with a little practice becomes an expert cruciverbalist. She enters the citywide crossword puzzle tournament, but is crushed when she finds out that Homer bet against her in the championship match. Homer proves his love for Lisa with a little help from New York Times crossword puzzle editor Will Shortz and master crossword constructor Merl Reagle.

The Simpson family takes a trip to the Mapple Store at the Springfield Mall where Lisa gets her very own Mypod, and Bart interrupts an announcement from Steve Mobbs with his own voiceover, causing pandemonium to break loose in the store. On his way home from the mall, Bart narrowly escapes punishment and befriends a Muslim boy named Bashir. Homer becomes suspicious of Bart’s new friend and invites Bashir, his mother and his father over for dinner so he can investigate their supposed anti-American sentiments. Having already offended Bashir and his family at dinner, Homer goes to their home to apologize, but he instead snoops around their house, a la Jack Bauer, and uncovers what he believes to be a terrorist plot to blow up the Springfield Mall. The race is on as Homer tries to warn the residents of Springfield about the impending disaster.

During the annual billionaires’ retreat, Mr. Burns wins the Boston Celtics in a casual game of poker. While hosting the season opener in Springfield, Mr. Burns witnesses the antics of Dallas Mavericks owner Mark Cuban. Fascinated with his behavior, Mr. Burns decides that the best way to win over the fans is to build a brand new, state-of-the-art sports arena. Unfortunately, the last remaining bee colony in Springfield is located on the proposed stadium site, and Lisa is single-handedly spearheading a movement to protect them. As Lisa fights for a safe haven for the bees, Homer attempts to help the quickly diminishing bee population by mating the Springfield bees with Africanized bees, creating a buzzworthy fiasco.

Lisa meets a new girl named Juilet and helps her write stories about a fantasy world called Equalia, but spending too much time with Juilet (and the story) begins to warp Lisa's sense of reality.

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 is informed that he and a select group of students have received perfect scores on a practice test for the upcoming Vice President's Assessment Test. As a result, he will be exempt from taking the real exam and will be transported by helicopter to a pizza party. However, Bart and the others soon realize their trip is not what it seems, and their day turns into an adventure all its own.

After too many years of financing Homer’s annual Mardi Gras party with home equity loans, their adjustable-rate mortgage skyrockets and the Simpsons are forced to put their house up for sale. Flanders does a good deed and purchases the property, becoming Homer and Marge’s new landlord. But when Homer publicly accuses Flanders of neglecting the Simpsons’ unsafe living conditions, Flanders threatens to throw the family out on the streets.

When Maggie disappears at a convent, Lisa goes undercover as a nun to solve the mystery. Meanwhile, Homer tries to keep Maggie’s disappearance a secret from Marge, who was blinded while watching a solar eclipse.

The family travels to Ireland to take Grandpa to have one last beer at his beloved Flanagan’s Pub, only to discover the little town of Dunkilderry isn’t the quaint little Irish village anymore and Flanagan’s Pub is rundown and nearly empty. Homer and Grandpa buy the pub from Tom Flanagan (guest voice Colm Meaney), and with a little help from Moe, try to bring it back to life amidst the ultra-hip, hardworking sober yuppies of the small Irish town, and put ‘Simpson & Son’ on the map.

When Homer and Marge’s marriage turns out to be invalid because Reverend Lovejoy was not licensed at the time, Homer asks Marge to marry him again. But when Homer mysteriously disappears on their wedding day, Bart and Lisa search for answers and are led on a cryptic trail of clues, leading them to Sideshow Bob. Meanwhile, Homer finds himself chained to a pipe in a dark room. When a mysterious voice tells him that the key to unlock his chains is inside a lollipop, he frantically eats it only to discover the lollipop is made of fiery hot sauce and he is tormented as Bart and Lisa race to save him

In an effort to spend more time with Maggie, Homer takes her to happy hour at Moe’s. While at the bar, Moe tells Homer about his new love, Maya, a woman he met on the internet. When Moe finally meets Maya in person, she is just as beautiful as her photos but he can’t help but notice one small detail: she is three feet tall. In order to make the relationship work, Moe must learn to love their differences.

When Bart and Milhouse pull off a prank at Springfield Elementary, Milhouse takes the fall and gets suspended from school. Homer forces Bart to sign in under Homer’s name and visit Grampa at his retirement home, and Bart soon becomes smitten with a delightful 11-year-old volunteer named Jenny. Hoping to impress Jenny, Bart offers to volunteer at the home. But as Bart and Jenny’s relationship progresses, Milhouse emerges from his suspension and is less than thrilled about Bart turning his back on him for a girl. Meanwhile, Lisa does a report on what Springfield will look like in 50 years and becomes very depressed at the dreary outlook. A concerned Marge takes Lisa to a psychiatrist who diagnoses Lisa with Environment-Related Despair and puts on her on an antidepressant to cure her eco-blues.

When Homer observes Bart and Lisa struggling in certain aspects of their academic and social lives at school, he becomes a proponent of “helicopter parenting,” the process of closely monitoring a child and forcing them to succeed. Homer takes hovering to a new level when he chooses a nearly impossible subject for Bart’s balsa wood model-building competition and gives Lisa some not-so-friendly advice on how to make friends. Meanwhile, Marge discovers a sauna in the Simpson family’s basement that she finds hard to resist.

When Marge learns Springfield Elementary is the worst school in the state, she and Homer rent an apartment in the upscale Waverly Hills neighborhood so Bart and Lisa can attend a better school. When Lisa is ostracized by the popular girls at Waverly Hills, Bart uses his newly established bad boy image to impress the other students and increase Lisa’s popularity by telling everyone she is best friends with the pop star Alaska Nebraska. However, when Alask comes to town, Lisa is left wishing Bart had never opened his big mouth. Meanwhile, Homer moves into the new Waverly Hills apartment to make it look like someone is living there, and he quickly gets used to the bachelor lifestyle.

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. To prove their point, they 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 (guest voice Jodie Foster) as the idealistic architect protagonist from Ayn Rand’s “The Fountainhead”.

When nearby 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.