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- Inspired by a movie about a girl who enters a tango contest and wins, Lisa decides to sign up for dance lessons -- and ends up taking tap lessons from a former child star. Meanwhile, Bart and Milhouse hide out at the mall to escape going to summer camp.
- After their vacation in the woods is cut short due to a mosquito infestation, The Simpsons stop by at an Indian casino, where Bart tries to sneak in and ends up in the office of an Indian mystic who shows Bart's future in the year 2030 as a washed-up rock star living with Ralph Wiggum while Lisa is the President of the United States trying to get the country out of financial trouble.
- Guest star: Betty White
- Guest star: Britney Spears
- Principal Skinner hires Fat Tony's construction company to build wheelchair ramps for the school. These ramps promptly break down, forcing Skinner to close down Springfield Elementary. However, a toy company led by Jim Hope takes over the school; in school, the children are only taught to provide marketing schemes and suggestions. Soon, a new toy called Funzo that mysteriously resembles the children's ideas is invented. After a brief showdown Gary Coleman and the Funzo, things return to normal as Burns decides to fund the school after a visit from the three Christmas spirits.
- Guest star: The B-52's
- Guest star: Mark McGwire
- Guest stars: Jim Forbes and Willie Nelson
- Guest star: Parker Posey
- Otto dumps his fiancee, Becky, at the altar, leaving her to become the Simpsons' latest houseguest, prompting Marge to go insane when Patty and Selma scare Marge with thoughts of Becky replacing Marge as a wife and mother. Meanwhile, Springfield Elementary gives Bart's fourth grade class videocameras and Bart sets out to create a movie.
- Barney realizes how much of a pathetic drunk he is after watching his birthday party video and decides to give up alcohol forever, which doesn't sit well with Homer. Meanwhile, Bart and Lisa work together to take a memorable photo for a new phone book cover contest.
- After getting his face censored out on the Duff Calendar for not being photogenic, Moe gets plastic surgery and becomes the star of a popular soap opera. Meanwhile, Bart and Lisa go after Maggie's pink elephant balloon after it floats away.
- Homer wins a Harley-Davidson motorcycle at a fifties dancing contest and starts his own biker gang, naming it "Hell's Satans". However, this attracts the real biker gang called "Hell's Satans" to crash at their house. However, after a while, they begin to appreciate Marge, who takes care of them, and kidnaps her. Homer tracks them down and scuffles with Meathook, the leader. At Marge's suggestion, the gang settles down and lives normal lives.
- Inspired by a cheesy "Zorro" movie, Homer begins slapping people with a glove and challenging them to duels , but when a real Southern gentleman accepts Homer's request for a duel, the Simpsons run off to the old farm Homer lived in with his parents and breed a dangerously addictive but successful tobacco/tomato hybrid called "tomacco". Just when they are about to gain a hundred million dollars from the hybrid, dangerously addicted animals ruin their plan. Homer proceeds to duel, only to get shot in the arm.
- Homer becomes a food critic for a Springfield newspaper and ends up annoying the restaurant owners of Springfield after he makes negative reviews just to be mean, advice he took from fellow critics. Springfield's restaurant owners then attempt to kill Homer by feeding him a poisoned éclair.
- Guest star: Shawn Colvin
- In a parody of VH1's Behind The Music, viewers take an inside look at The Simpsons' rise to fame--and the many scandals, feuds and break-ups that threatened to end the show and split up the family.
- Homer has a nervous breakdown when it's revealed on a quiz that he only has three years left to live. To calm him down, the family goes to Florida for vacation--and end up in the middle of a raucous spring break, where Homer joins in on the party and ends up getting himself and his family in trouble for killing the county's beloved mascot: an alligator named Captain Jack.
- Homer gets in trouble with PBS after confessing he doesn't have $10,000 to give them for their pledge drive--and ends up a missionary on a South Pacific island.
- Maude Flanders is killed in a freak accident during a stock car race, devastating Ned and prompting Homer to find a new woman for his grieving neighbor. However, Ned begins losing his faith in God before being prompted back by a Christian rock band.
- Guest stars: Bachman–Turner Overdrive and Jim Cummings
- The Simpsons rescue a diving horse named Duncan from abuse and keep it as a pet , but when the cost of upkeeping the horse rises, Homer and Bart train Duncan to be a racing horse. Meanwhile, Lisa is upset over her school losing the band competition to Ogdenville unfairly at the state fair and writes a letter to Bill Clinton in protest.
- Mr. Burns goes to the Mayo Clinic for a checkup after being declared the oldest man in Springfield, leaving the Simpsons to house-sit for him and Homer to take advantage of living as a rich man. However, when Homer wants to throw a party, he goes to Moe's, where he must buy the alcohol in international waters as it is Sunday before 2 PM. There, they are captured by Chinese pirates. Later, Burns discovers that as a result of having all the existing diseases, he is perfectly healthy as all the germs simply cancel each other out. Consequently, he returns and kicks out the Simpsons, who haven't even enjoyed being rich, causing Homer to be extremely bitter and resentful.
- While the Simpson family goes skiing, Marge remains at the ski lodge due to her fear of skiing, only to break her leg from a falling clock. As a result, while hospitalised, Marge leaves Lisa to deal with the slovenly Bart and Homer, who do nothing but take their toll on their house. However, in an attempt to motivate them, she pulls a prank suggested by the ghost of Lucille Ball on Bart and Homer by making it look like they have leprosy. At Ned Flanders' suggestion, Bart and Homer end up in Hawaii; with them gone, Lisa finishes cleaning the house as Marge arrives home, her cast off. The pair then go to retrieve Homer and Bart, who are enjoying themselves despite the shock therapy.
- Guest stars: John Goodman, Henry Winkler, Jay North and NRBQ
- Guest stars: Garry Marshall and Butch Patrick
- After Manjula gives birth to octuplets that were the result of fertility drugs, she and Apu unintentionally allow a zookeeper to exploit their babies in exchange for help after corporate sponsors abandon them for a mom that has given birth to nontuplets in Shelbyville. After a failed rescue attempt by Homer and Apu, the zoo keeper agrees to return the babies only if Butch Patrick and Homer ride a tricycle dressed as Eddie Munster on stage while attacked by cobras.
- Homer becomes a local celebrity after bowling a 300 game, but his fame quickly fades as "yesterday's news". After a botched suicide attempt foiled by Otto, Homer decides to spend time with Maggie after seeing Ron Howard spend time with his children. When Homer tries to teach Maggie swimming, he fails due to her mistrust of him, and has to pulled out the beach by Maggie. Eventually, Homer brings Maggie to a bowling game, where she bowls a perfect game.
- Intro: The Simpsons watch Kang and Kodos's lame attempt at a Halloween variety show.
I Know What You Diddily-Iddily Did – Marge accidentally runs over Ned Flanders and is haunted by claims that someone knows what she did, only to realize that Ned survived because he became a werewolf.
Desperately Xeeking Xena – Bart and Lisa gain super powers after a freak accident at school and must save Lucy Lawless from the Collector .
Life's A Glitch, Then You Die – When the Y2K bug causes everything electronic and computer generated in the world to go haywire, the family searches for a way out.
- After getting in trouble for flooding the school gym during Fire Prevention Day, Bart is revealed to be diagnosed with Attention Deficit Disorder and prescribed a Ritalin-esque drug called Focusyn. At first, the drug makes Bart well-behaved and intellectual, but soon, Bart becomes paranoid, claiming that there are satellites owned by Major League Baseball that are spying on the town. When ordered to stop, Bart refuses, devours a few hundred, and proves his theory right by destroying the satellite with a tank. All is restored when Bart goes back to his ordinary pills.
- Guest stars: Mel Gibson and Jack Burns
- After destroying an "Elec-Taurus" electric car in a test run, the Simpsons are given free tickets to Mel Gibson's new film, a remake of Mr. Smith Goes to Washington. Mel Gibson, however, laments his current role without violence and wants someone to give him criticism. When Homer sees Mel talking with Marge, he gives Mel a brutal review, leading Mel to believe that Homer is the only man brave enough to give suggestions. As a result, he hires him to create a better ending. However, when the ending proves to be too controversial, Mel and Homer end up on the run from studio executives with the film.
- Guest stars: Kid Rock, Joe C., Robert Evans, Charlie Rose and Diedrich Bader
- Guest star: Don Cheadle
- Bart believes he has the power to heal others through faith after removing a bucket glued to Homer's head. However, when Bart knocks Milhouse's glasses off in order to cure his myopia, Milhouse is nearly run over by a truck that he thinks is a dog as he cannot see without his glasses. Consequently, Bart, feeling guilty, ends his career as a faith healer. Meanwhile, Homer creates a homecoming game float for Springfield University. However, he soon forgets about it, and accidentally injures the star player, Anton Lubchenko. After getting in trouble with Fat Tony, Homer is saved when Lubchenko sacrifices his leg to win the game; the leg is surgically reattached by Doctor Hibbert, who is relieved at the end of Bart's healing career.
- Guest star: Elwood Edwards
- Guest stars: Gary Coleman, Tim Robbins and Clarence Clemons
- Guest stars: Ron Howard, Pat O'Brien, Nancy O'Dell and Penn & Teller
- Guest stars: Dick Clark, Tom Arnold and Lucy Lawless
- Guest star: Edward Asner
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