Best. Episodes. Ever.
sideshow bob episodes first, then other episodes in season order
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- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightHomer is forced to become a department store Santa when Marge spends the family's Christmas savings on removing Bart's tattoo.
- DirectorBrad BirdStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Krusty is found guilty of robbing the Kwik-E-Mart following Homer's eyewitness testimony, Bart and Lisa set out to prove his innocence.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightSideshow Bob gets out of jail and plots to take his revenge on Bart by marrying his Aunt Selma and killing her.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightAfter being released from prison on parole, Sideshow Bob plots to murder Bart.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightWhen Sideshow Bob is released from prison and is elected Mayor of Springfield, Bart and Lisa suspect foul play and are determined to expose his corruption.
- DirectorDominic PolcinoStarsDan CastellanetaJulie KavnerNancy CartwrightSideshow Bob again escapes from prison and takes control of a TV screen at an air show, demanding all television stations immediately go off the air.
- DirectorPete MichelsStarsDan CastellanetaJulie KavnerNancy CartwrightBart suspects a paroled Sideshow Bob is up to his old tricks when he is hired by his brother Cecil to assist in the construction of a dam.
- DirectorJim ReardonMichael MarcantelStarsDan CastellanetaJulie KavnerNancy CartwrightWhen a new television game show grows in popularity and begins to draw away Krusty's TV audience, he decides to retire from the television business.
- DirectorJim ReardonSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightHomer has to use Sideshow Bob in order to track down a potential assassin.
- DirectorDavid SilvermanMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightThe Simpsons become lost in Italy, finding their way to a small town that Sideshow Bob has become the mayor of.
- DirectorMark KirklandRob OliverStarsDan CastellanetaJulie KavnerNancy CartwrightBart is responsible for Sideshow Bob's death after his latest attempt at revenge is foiled, but is his death actually part of the plan?
- DirectorChuck SheetzMike B. AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer is kidnapped moments before he and Marge are supposed to re-renew their vows. However, Marge comes to the conclusion that Homer left her at the altar.
- DirectorMike B. AndersonNancy KruseStarsDan CastellanetaJulie KavnerNancy CartwrightBart is convinced that the Simpsons' new friendly, unassuming neighbor is actually Sideshow Bob in disguise.
- DirectorMike B. AndersonSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightMoe's gruff and abrasive personality makes him the perfect hyper-critical judge, and lands him a spot on American Idol. Meanwhile, Homer makes Marge uncomfortable when he starts spending more time at home with Moe's now closed.
- DirectorMike B. AndersonMatthew NastukStarsDan CastellanetaJulie KavnerNancy CartwrightThe town votes to kick the Simpsons out of Springfield, so they decide to move to the Outlands.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightBart ends up at a school for gifted children after cheating on an IQ test.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightAfter losing his job, Homer contemplates ending it all, until he discovers a new life path as a safety advocate.
- DirectorKent ButterworthGregg VanzoStarsDan CastellanetaJulie KavnerNancy CartwrightAfter being embarrassed by the rest of the family at a company picnic, Homer becomes obsessed with improving their behavior towards each other.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightHomer takes the family camping, but it soon becomes a misadventure when they lose their equipment and Homer is mistaken for Bigfoot.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightBart gets more than he bargained for when he saws the head off a statue of the town's founder.
- DirectorKent ButterworthDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightHomer and Marge enjoy a night on the town, leaving the kids with a diabolical babysitter, with a surprising secret.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightAfter seeing a motorcycle daredevil at a monster truck show, Bart becomes a death-defying daredevil skateboarder.
- DirectorDavid SilvermanMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightHomer tries to set Selma up with Principal Skinner, only for him to fall for Patty instead.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightHomer meets his half-brother Herb Powell, an automobile tycoon who zealously bonds with the family and tasks Homer with designing a car for the average American.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Grampa's new girlfriend dies and leaves him $106,000 in her will, he tries to decide what to do with it.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightLisa has a crush on her substitute teacher; Bart decides to run for class president.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightBart, Milhouse and Martin each pitch in to buy an highly-collectible "Radioactive Man" comic book, which soon has a disastrous effect on their friendship.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Bart saves Mr. Burns' life with a donated blood transfusion, Homer vows revenge when they receive only a "thank you" card as compensation.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightHomer accidentally lands in a mental hospital and ends up sharing a room with a white man who thinks he is Michael Jackson.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightAfter wishing for Flanders to lose his business, Homer discovers that his neighbor is actually about to go bankrupt and decides to help him out.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightAfter having a horrible day, Bart gets a job tending bar for a group of gangsters and becomes the prime suspect when Principal Skinner mysteriously disappears.
- DirectorBrad BirdJeffrey LynchStarsDan CastellanetaJulie KavnerNancy CartwrightBart and Lisa try to reunite Krusty the Clown with his father.
- DirectorRich MooreAlan SmartStarsDan CastellanetaJulie KavnerNancy CartwrightMoe claims a drink that Homer invented is his own, with the drink making the bar a local hot spot, but threatens his friendship with Homer.
- DirectorJeffrey LynchStarsDan CastellanetaJulie KavnerNancy CartwrightAfter aptitude tests seemingly indicate that they are best-suited to police work and homemaking respectively, Bart is made hall monitor while Lisa becomes a delinquent.
- DirectorCarlos BaezaStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Bart receives a microphone which can transmit through radios, he decides to pull a series of pranks and eventually convinces the town that a boy has fallen down a well.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Otto loses his job as school bus driver because he does not have a license, Bart convinces Homer and Marge to let Otto stay with them until he gets back on his feet.
- DirectorRich MooreStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Homer "wins" a $2000 settlement from the plant due to radiation-induced sterilization, his half-brother Herb sees an opportunity to regain his fortune.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightBart and Lisa attend "Kamp Krusty" but it is nothing like they thought it would be; Homer's hair grows back and he loses weight while the kids are away.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightYears of poor eating habits catch up with Homer when he suffers a massive heart attack, but the family can't afford the triple bypass operation he needs.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightWhen Mr. Burns revokes the plant's dental plan, forcing Lisa to be fitted with cheap, ugly braces, Homer leads its union into going on strike.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightWhen Krusty's show is canceled after losing viewers to a ventriloquist and his dummy, Bart and Lisa organize a celebrity-filled comeback special for their favorite clown.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightAfter the kids find a record with Homer's picture on it, he recalls the story of how he achieved fame in the 1980s with his barbershop quartet, The Be Sharps.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightAfter his birthday party goes wrong, Mr. Burns begins to want his childhood toy, a teddy bear named Bobo; Homer finds that Maggie is in possession of the doll.
- 1989– 30mTV-148.6 (3.7K)TV EpisodeDirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightMr. Burns builds a casino when Springfield decides to legalize gambling, with Marge becoming addicted to the slot machines.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightBart becomes an overnight sensation as the "I didn't do it" boy on Krusty the Clown's show.
- DirectorCarlos BaezaStarsDan CastellanetaJulie KavnerNancy CartwrightIn an effort to increase the dismal television ratings for their space launches, NASA decides to send an ordinary man into space, and Homer is chosen for the task.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightAfter a close brush with death, Mr. Burns decides to find an heir to his empire, and chooses Bart because of his truly devious nature.
- DirectorJeffrey LynchStarsDan CastellanetaJulie KavnerNancy CartwrightBart witnesses the alleged assault of a waiter by Mayor Quimby's nephew, but coming forward will mean admitting to skipping class and facing the consequences.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightConfined to his room with a broken leg, Bart suspects Ned Flanders of murdering Maude; the family's new swimming pool earns Lisa popularity among the neighborhood kids.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightThe family's job at Mr. Burns' country estate goes awry when Homer goes mad; Homer's attempt to repair a toaster results in inadvertent time travel; The school staff turn cannibalistic.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightBart falls for Reverend Lovejoy's daughter and is surprised when she becomes a bad influence on him.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer becomes a member of a mysterious organization called the Stonecutters and is heralded as "the chosen one".
- DirectorSwinton O. Scott IIIStarsDan CastellanetaJulie KavnerNancy CartwrightHomer recounts the story of Maggie's birth when the kids ask why there are no photos of her in the family album.
- DirectorBob AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightBart discovers a comet that is on a collision course with Springfield.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightHomer becomes a Krusty the Clown stand-in, but is mistaken for the real Krusty by the Springfield mafia.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightThe citizens of Springfield host their own film festival, with popular movie critic Jay Sherman arriving from New York to judge.
- DirectorSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightWhile Bart is hospitalized, Lisa runs into her old mentor Bleeding Gums Murphy, who is also a patient, and becomes devastated when he dies soon after.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightMarge joins the Springfield Police Department to fight crime and corruption, only to find herself rescuing Homer when he gets mixed up in a counterfeit jeans operation.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightWhen a group of Shelbyville kids steal Springfield's sacred lemon tree, Bart and his friends venture there to get the tree back.
- DirectorJeffrey LynchStarsDan CastellanetaJulie KavnerNancy CartwrightAfter Mr. Burns steals oil from Springfield Elementary and blocks out the sun, an unknown person shoots him.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightWhile Mr. Burns is hospitalized, an investigation into his shooter begins; although Smithers initially suspects himself, a trace of Simpson DNA narrows down the list of possible culprits.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightA Hollywood film crew shoots an adaptation of the "Radioactive Man" comics in Springfield, with Rainier Wolfcastle in the title role and a reluctant Milhouse as his sidekick, Fallout Boy.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightMarge and Homer lose custody of the kids, who are sent to live at the Flanders' house.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightBart casually sells his soul to Milhouse for $5 but soon regrets it; Moe converts his dank bar into a family restaurant.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightA trip to a local petting zoo convinces Lisa to give up meat, despite excessive pressure to convince her not to do so.
- DirectorBob AndersonDavid MirkinStarsDan CastellanetaJulie KavnerNancy CartwrightA lightning storm causes giant advertising mascots to come to life; The children are terrorized by Groundskeeper Willie in their dreams; Homer finds himself trapped in another dimension.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer intentionally gains more weight in order to qualify for disability and work from home, but soon realizes that being morbidly obese comes with its own problems.
- DirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightAfter faking his own death, Homer is reunited with his mother, who harbors a deep secret.
- 1989– 30mTV-147.4 (2.8K)TV EpisodeDirectorDavid SilvermanStarsDan CastellanetaJulie KavnerNancy CartwrightTroy McClure hosts a retrospective of the first 137 episodes of The Simpsons (1989).
- DirectorSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightMarge's relationship with Bart is strained when he is caught shoplifting before Christmas.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightHomer starts a bowling team with Moe, Apu and Otto, but Mr. Burns insists on joining after learning that the team was funded with his money; Springfield Elementary introduces uniforms.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightFormer President George Bush and his wife, Barbara, move into the Simpsons' neighborhood and soon clash with Bart and Homer.
- 1989– 30mTV-147.7 (2.7K)TV EpisodeDirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightAfter buying a Chanel suit at a bargain price, Marge is invited to a country club by a former schoolmate, where she desperately tries to fit in with its upper class clientele.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightKrusty the Clown is left almost broke after Bart inadvertently rats him out to the IRS, forcing Krusty to take drastic action.
- DirectorSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightWhen Smithers is forced to take a vacation, he appoints Homer as his temporary replacement.
- DirectorWesley ArcherStarsDan CastellanetaJulie KavnerNancy CartwrightBart and Lisa meet a vagabond who claims to be the creator of Itchy from "Itchy and Scratchy."
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightWashed-up movie star Troy McClure starts dating Selma in an attempt to silence bizarre rumors about his personal life and resuscitate his career.
- DirectorSwinton O. Scott IIIStarsDan CastellanetaJulie KavnerNancy CartwrightBart makes a fake driver's license and takes Milhouse, Martin, and Nelson on a huge road trip; Lisa spends time with Homer at the power plant.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightA series of vignettes showcasing a day in the life of various Springfield residents.
- 1989– 30mTV-148.5 (3.1K)TV EpisodeDirectorJeffrey LynchStarsDan CastellanetaJulie KavnerNancy CartwrightAfter surviving multiple assassination attempts by Mr. Burns to inherit a cache of artwork they stole from the Nazis, Grampa teams up with Bart to recover the paintings.
- DirectorMike B. AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightThe Simpsons move to Cypress Creek, where Homer unwittingly works for a charismatic supervillain; the rest of the family struggles with the transfer.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightThe Simpsons try to reunite Mr. Burns with Larry, his slovenly long-lost son.
- DirectorBob AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightAfter a hurricane destroys Ned Flanders' house, he suffers a nervous breakdown and is forced to confront repressed problems from his childhood.
- DirectorBob AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightAfter alcohol is banned in Springfield, Homer adopts the moniker of the "Beer Baron" to bootleg liquor, prompting an investigation from an uptight Treasury agent.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightBart discovers Principal Skinner and Mrs. Krabappel kissing, and it's not long before the whole town knows of their secret affair.
- DirectorMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightBurns loses his fortune and recruits Lisa to help him get it back.
- DirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer's laziness begets the ire of his industrious but arrogant new co-worker Frank Grimes; Bart buys a run-down factory for a dollar.
- 1989– 30mTV-PG9.0 (5.1K)TV EpisodeDirectorJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer must travel to New York to get his car back, which is illegally parked at World Trade Center Plaza.
- DirectorJim ReardonMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightHomer battles mutants after Springfield is annihilated by a neutron bomb; Bart has his DNA mixed with a fly; Marge is revealed to be a witch in colonial Springfield.
- DirectorPete MichelsJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightAfter a massive soccer riot, Homer purchases a gun to protect the family.
- DirectorJim ReardonNeil AffleckStarsDan CastellanetaJulie KavnerNancy CartwrightTownspeople believe that Lisa has unearthed the fossilized remains of an angel.
- DirectorJim ReardonSwinton O. Scott IIIStarsDan CastellanetaJulie KavnerNancy CartwrightMarge becomes a real-estate agent.
- DirectorJim ReardonMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightBart and Homer befriend two carnies and invite them to stay with them, but the carnies soon swindle the Simpsons out of their house.
- DirectorJim ReardonSteven Dean MooreStarsDan CastellanetaJulie KavnerNancy CartwrightAn evil cult called the Movementarians brainwashes the citizens of Springfield and it's up to Marge to get them back.
- DirectorJim ReardonMike B. AndersonStarsDan CastellanetaJulie KavnerNancy CartwrightAfter a disastrous performance, Krusty changes his image and becomes an edgy stand-up.
- DirectorDominic PolcinoJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer and Moe attempt insurance fraud so that Moe can support his new girlfriend. When Homer ends up in jail, Moe has to decide whether or not to come forward.
- DirectorSusie DietterStarsDan CastellanetaJulie KavnerNancy CartwrightLisa fears she is losing her intelligence when she learns about the fabled Simpson gene. Meanwhile, Jasper freezes himself in the Kwik-E-Mart freezer.
- DirectorNeil AffleckJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightBart is reluctant to hang out with Ralph Wiggum, until he gains access to Chief Wiggum's master key to the city.
- DirectorJim ReardonMark KirklandStarsDan CastellanetaJulie KavnerNancy CartwrightBart and Lisa become locked in competition when they anchor a children's news program; Homer adopts a helper monkey.
- DirectorDominic PolcinoJim ReardonStarsDan CastellanetaJulie KavnerNancy CartwrightHomer and Bart try to start their own grease business; Lisa organizes a school dance.