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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 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.
In order to save up money to buy a cell phone, Bart takes a job at a country club retrieving golf balls. While at the course, Bart watches celebrities, including Leary (guest-starring as himself) playing a round. When Leary's cell phone rings just as he is about to take a swing, he furiously throws the phone in the air and it lands right next to Bart. Bart decides to keep the cell and makes prank calls to all over the world pretending to be Leary. He even accepts a job offer from famed producer Grazer (guest-starring as himself) to star in the film version of "Everyone Poops." When Marge discovers what Bart has been up to, she confiscates the device and calls Leary to return the phone. But Leary has a better idea, and instructs Marge to activate the GPS system on the phone so she can track Bart's every move. Bart quickly catches on and devises a plan that sends the 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 (guest-voicing as himself) 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.
Three chilling tales of Halloween horror unwind in THE SIMPSONS annual "Treehouse of Horror" Halloween special. First, Homer kills off celebrities so their likenesses can be exploited free-of-charge in "How to Get Ahead in Dead-Vertising." Next, Transformer-like robots duke it out in Springfield in "Untitled Robot Parody." And in "It's the Grand Pumpkin, Milhouse," Lisa accompanies Milhouse to a pumpkin patch to await the appearance of the Grand Pumpkin, but when he finally appears, the Grand Pumpkin goes on a rampage to avenge all the pumpkins carved and tortured in the name of Halloween. Also, the highly-anticipated episode opener features Homer Simpson as he attempts to cast his ballot for the 2008 Presidential election with a deadly twist.
When the Simpson family takes a road trip to a cabin in the woods, a series of flashbacks depict Homer and Marge's blissful courtship and their early married years. They recall their first encounter with Flanders and Maude twenty years prior at the very same cabins, where Flanders insisted the unmarried Homer and Marge stay in separates rooms. Later, they recall when they each met distracting members of the opposite sex who nearly wooed Homer and Marge away from each other. Bart and Lisa also reflect on happier times from their early childhood. Despite the obstacles and the passing of time, Homer and Marge attempt to see the forest for the trees.
Lisa discovers her amazing talent for doing crossword puzzles and becomes an expert cruciverbalist, and she soon enters a citywide crossword puzzle tournament. Homer, short on cash after abandoning his "Sweet Conclusions" professional break-up artist business, goes to cheer Lisa on at her tournament and discovers an underground crossword puzzle betting ring. In the ultimate betrayal, Homer profits from betting against Lisa in the championship match. When the heartbroken Lisa finds out, Homer must spell out his love for her with a little help from New York Times crossword puzzle editor Will Shortz (guest voice as himself) and master crossword constructor Merl Reagle (guest voice as himself).
The Simpson family takes a trip to the Mapple Store at the Springfield Mall where Lisa get 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 (guest voice Shohreh Aghdashloo) 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 (guest voice as himself). Fascinated with his behavior, Mr. Burns decides to emulate Cuban's over-the-top crowd pleasing stunts in order to win over the hearts of Springfield's basketball fans. In the midst of his failing endeavor, 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 an equally academic and creative new friend named Juliet (guest voice Emily Blunt), and together they construct a fantasy world that takes them both a little too far from reality.
When Mayor Quimby inducts Vance Connor into the Springfield Walk of Fame, Homer recounts how he ran against Vance for class president in high school and lost. After a little digging, Homer learns that the election had been rigged, and he wonders what course his life would have taken if only fate had smiled on him. Homer soon meets an old Italian cook at Luigi's Italian Restaurant whose magical tomato sauce, when stirred in just the right way, reveals what Homer's life would have been like had he won the election. However, when Homer gets a chance to see what his life could have been, he wonders if fate was actually been on his side all along.
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. Shocked at how Bart could have performed better than she did, Lisa freezes up when it comes time for her to take the exam. However, Bart and the others soon realize their trip is not what it seems, and their day turns into an adventure all its own. Meanwhile, when Homer is late on making an insurance payment, he must avoid bodily accidents at all costs until his insurance check is cashed, making for one very tense afternoon.
After too many years of financing Homer's annual Mardi Gras party on home equity loans, Homer and Marge's adjustable-rate mortgage skyrockets and they are forced to put their house up for sale. Flanders does a good deed by outbidding Mr. Burns and purchasing the property, thus 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 Homer leaves Maggie on the doorstep of a convent to keep her safe as he rescues Santa's Little Helper from a sticky situation, the nuns at the convent take Maggie in. Lisa comes up with a plan to infiltrate the convent and rescue Maggie. After deciphering a series of cryptic messages at the convent, Lisa sets off to find Springfield's most coveted jewel and gets a little help from an ancient order of mystery buffs led by Comic Book Guy and Principal Skinner. But when Springfield's Freemasons, led by Mr. Burns, get wind of Lisa's quest, she must race to solve the mystery and find Maggie.
The Simpson family travels to Ireland to take Grandpa to have one last beer at his beloved O'Flanagan's Pub in Dunkilderry. However, when they arrive, the little town of Dunkilderry isn't the quaint little Irish village that Grandpa remembers. It has become a gentrified yuppie enclave filled with hipsters on laptops and Bluetooths, surrounded by swanky stores and coffee shops. When they track down O'Flanagan's Pub, the bar is run down and nearly empty. After a few spirits, Homer and Grandpa buy the pub from Tom O'Flanagan, and they are left with trying to bring the bar back to life amidst an ultra-hip, hardworking and sober Irish town. With a little help from Moe, they find the perfect scheme to bring the pub back to life 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 Alaska Nebraska 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 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.