When he wears a pink shirt to work, Homer's coworkers mistake him for a mental patient and commit him to the New Bedlam Rest Home for the Emotionally Interesting. While there, Homer meets a tall, stocky white man who claims to be Michael Jackson. Despite his reservations, Homer befriends Michael and takes his new pal home with him upon his release. Meanwhile, Lisa celebrates her eighth birthday without a present from Bart, who was too inconsiderate to get her anything. With Michael's help, Bart writes a special song for Lisa that proves to be the best gift she ever received. Witnessing the tender scene, Michael admits that he's really Leon Kompowsky, a bricklayer.

Lisa enters an essay contest and wins a trip for the whole family to go to Washington, D.C. While there, her faith in democracy is shattered when she witnesses a congressman accepting a bribe. In her desire to uphold this nation's ideals, Lisa decides to expose the corrupt official, and in doing so has him arrested in a sting operation.

Ned Flanders decides to open his own business called the Leftorium, a store that sells tools and products aimed at left-handed consumers. Homer, filled with resentment towards Flanders, hopes that the Leftorium fails. Needless to say, the business is not a smashing success and Flanders goes broke, forcing his family to sell their furniture and possessions in a tag sale. Wracked with guilt, Homer enlists all of the left-handed people he knows to buy Flander's wares and save his neighbor from financial ruin.

When he crashes his skateboard into the stairwell of the Legitimate Businessman's Social Club, Bart falls in with a particularly bad crowd: the Springfield Mafia. Soon, he befriends Fat Tony, Louie, Joey and other goodfellas, who take him on as their bartender and errand boy. As Bart adopts more and more gangster-like traits, Marge grows anxious. Meanwhile, Principal Skinner disappears and the police strongly suspect that Bart and his new friends are responsible. During the sensational trial, Fat Tony turns stool pigeon and rats out Bart as Skinner's killer. Nobody can save Bart but Skinner himself, who emerges from his hiding place to explain that neither Bart nor the Mob did anything to him.

During a near-fatal meltdown at The Springfield Nuclear Power Plant, Homer frantically presses buttons on his console until he hits the right combination and saves the day. Homer becomes a hero even though he knows in his heart that what he did was a fluke. Aristotle Amadopolis, owner of the Shelbyville Nuclear Power Plant, invites Homer to make a speech for the employees at his plant, and Homer is once again faced with a meltdown. This time, he isn't so lucky and he sees his reputation destroyed just as quickly as it was made.

During a tear-filled dinner at the Simpsons' house, Krusty the Clown reveals that he is the estranged son of an Orthodox Jewish Rabbi. It seems that Krusty's father, Rabbi Krustofski, never accepted his son's profession, and disowned him years ago. Bart and Lisa decide to reunite the two men, but find that getting the Rabbi to agree to a meeting is nearly impossible. After endless research by Lisa, and repeated negotiations by Bart, the Rabbi agrees to meet with his clown son, and the two men are reunited and appear together on The Krusty the Clown Show.

After eating piles and piles of Halloween candy, Bart, Lisa and Homer have nightmares that haunt them all night. The Monkey's Paw; Lisa dreams that the family goes on a trip to Morocco and buys a cursed monkey paw that grants its owner three wishes. By wishing for world peace, Lisa accidentally paves the way for an alien invasion by Kang and Kodos, who enslave the human race. The Bart Zone; Bart's dream, in which he has the power to read minds and affect people with his thoughts, seems less like a nightmare at first. But eventually, he realizes he's used his powers for evil and repents. If I Only Had A Brain; Homer dreams that Mr. Burns steals his brain for a giant robot he's building. Due to an accident, Mr. Smithers is forced to sew Mr. Burns' head onto Homer's body, creating a horrific two-headed creature.

When Homer disappoints Lisa one too many times, he tries to make it up to her with one grand gesture: He buys her a pony. Lisa is thrilled, but Homer and Marge are shocked to discover how expensive maintaining the animal can be. Homer is forced to take on another job working the graveyard shift at the Kwik-E-Mart to pay the bills. When she realizes her father is overworked, Lisa decides to give up her pony.

Bart becomes deeply immersed in competitive soapbox racing while Homer begins to realize that he's not as good a father as he thought. After attending a lecture at National Fatherhood Institute, Homer becomes a more attentive father, helping Bart build the ultimate soapbox racer. But Bart decides not to use it in his big race against Nelson Muntz, instead opting to borrow Martin Prince's scientifically engineered aerodynamic racer. Homer is devastated by Bart's rejection, but still attends the race and watches as Bart beats Nelson.

Homer invents a bizarre drink he calls the Flaming Homer. It's so good that Moe steals his recipe, renames it the Flaming Moe, and takes credit for it. The Flaming Moe revitalizes the bartender's business, turning Moe's Tavern into the hottest spot in Springfield. Meanwhile, Homer is so angered by Moe's stealing of his idea that he sabotages Moe's chance to sell the recipe for the Flaming Moe to representatives of Tipsy McStagger's bar and grill franchise. Realizing he shouldn't have taken credit in the first place, Moe makes him a Flaming Homer on the house.

Mr. Burns sells The Springfield Nuclear Power Plant for $100 million. The buyers are two wealthy German investors who promptly fire Homer and other employees. After a confrontation with Homer and others at Moe's, Mr. Burns realizes he should never have sold the plant. After negotiations, Burns buys back the plant and re-hires Homer, plotting to get revenge on him in the future.

It's a walk down memory lane as Homer and Marge recount their early years for Bart and Lisa. Back in 1980, a young Homer and Marge are forced to get married at Shotgun Pete's Wedding Chapel after Marge becomes pregnant. But married life is difficult for the young couple and Homer decides to leave Marge until he is able to provide the sort of life he thinks she deserves. Marge tracks Homer down at his new job at the Gulp 'N Blow and the two agree to stick it out and build a family together.

Homer buys Bart a Superstar Celebrity microphone for his birthday. Bart thinks it's the lamest gift in the world until he realizes he can play some great pranks with it. One of his pranks backfires when the entire town comes to the rescue of Timmy O'Toole, the little boy Bart pretends has fallen down a well. Krusty the Clown brings his celebrity friends, including Sting, to record a song We're Sending Our Love Down the Well to benefit Timmy. Realizing things have gotten out of hand; Bart tries to undo his prank, but winds up falling down the well himself. He eventually admits that there was no Timmy O'Toole and the whole town is angered because a 10-year-old boy took them for fools. The only people willing to dig Bart out of the well are Homer and Sting.

Homer discovers that Lisa has an uncanny ability to pick winning football teams. Soon, the two of them spend every Sunday afternoon together, betting on football games and winning. During these Daddy-Daughter Days, Lisa feels closer to Homer than ever, but she begins to feel betrayed when she realizes Homer is only interested in her winning picks. Lisa rebels by refusing to pick a winner for the Super Bowl until Homer apologizes for being selfish. They agree to have Daddy-Daughter Days after the end of the football season and continue to bond.

Marge has a nervous breakdown and is sent to Rancho Relaxo resort for some much-needed rest and relaxation. While she's off pampering herself, Homer sends Bart and Lisa to stay with their Aunts Patty and Selma but must take care of Maggie himself. During the night, Maggie disappears and Homer frantically runs around town looking for her. Spotted by the Springfield Police, Maggie is finally brought back to Homer and Marge returns from her vacation clueless about her daughter's little adventure.

During a particularly long detention jag, Bart discovers that his teacher, Mrs. Krabappel, has placed a personal ad looking for love. Thinking it would be funny to string her along, Bart writes her a love letter as Woodrow, the perfect man who loves holding hands and hates yo-yos. Mrs. Krabappel falls madly in love with Woodrow and Bart begins to realize that he's done a very cruel thing. With the help of his family, Bart writes a sweet goodbye letter and lets his teacher gently off the hook.

Mr. Burns makes a million dollar bet with his arch-rival Aristotle Amadopolis that the Springfield Nuclear Power Plant team will beat the Shelbyville Nuclear Power Plant team in the softball championships. To ensure victory, Burns hires a number of ringers, including pro baseball players Darryl Strawberry, Ken Griffey, Jr., Steve Sax, Roger Clemens, Jose Canseco, Don Mattingly, Ozzie Smith, Wade Boggs and Mike Scioscia to replace the plant employees he cut from the team. But as game day approaches, the pros all succumb to various strange ailments and accidents that prevent them from playing and it's up to Homer and his teammates to beat the Shelbyville team. With bases loaded and the score tied in the ninth inning, Homer is sent to bat and wins the game when the pitch hits him in the head and accidentally scores a homer.

After taking career aptitude tests, Lisa discovers that the occupation she's best suited for is homemaker while Bart is pegged as a future police officer. Each takes the opportunity to explore their options as Lisa spends the day doing chores with Marge and Bart goes on a ride along with the police. Lisa hates her role and rebels by becoming a troublemaker at school. Police life fits Bart like a glove and he becomes a hall monitor, handing out demerits to his classmates for minor infractions. When Lisa secretly steals all of the teachers' manuals, it's up to Bart and Principal Skinner to figure out who did it. Realizing his sister is the culprit; Bart takes the rap and returns to his life as a bad student and detention regular.

Santa's Little Helper is rushed to the hospital to undergo an emergency operation. Homer is saddened to tell Bart and Lisa that they just can't afford the $750 for the operation, but seeing how much everyone--including himself--loves the dog, he resolves to find a way to pay for it. To save up the money, everyone must give up their small luxuries and begin to resent the dog for forcing them to lose out on the things they enjoy. Hurt and dejected, Santa's Little Helper runs away from home, only to be adopted by Mr. Burns, who trains him to become one of his vicious attack hounds. After a long brainwashing process, Santa's Little Helper becomes a bloodthirsty killer. When Bart goes to Burns' mansion to retrieve his dog, Santa's Little Helper tries to attack him but remembers all the good times they had and snaps out of his brainwashed state. The dog then returns to the family that loves him.

Homer and Marge have a fight after attending a boring movie and Homer drives off angry. As he drives, he pulls up to a honky-tonk bar called Beer 'N' Brawl where he meets an aspiring country music singer named Lurleen Lumpkin. Struck by her talent and her beauty, Homer becomes her manager, securing her gigs and a record deal while at the same time fraying his relationship with Marge. Even though it's clear that Lurleen is falling in love with Homer, he resists her come-ons and signs away Lurleen's contract to another manager in order to be a better husband to Marge.

Selma agrees to marry her prison pen pal, Sideshow Bob. Bart and Lisa are terrified of their soon-to-be new uncle, since Bob swore he'd get revenge on Bart for having him sent to prison for framing Krusty the Clown for robbery. Sideshow Bob tries to show the Simpsons that he has changed his ways in prison, but Bart remains skeptical. His suspicion pays off when Bob tries to kill Aunt Selma on their honeymoon. Bart foils the plot and it's back to prison for Bob, back to spinsterhood for Selma.

After seeing Spinal Tap bring the house down (sort of) in concert, Bart decides he wants to learn how to play electric guitar. Playing is harder than Bart thought and he becomes dejected when he sees what a guitar god his bus driver, Otto, is. Because he was too busy jamming with Bart's guitar, Otto arrives late to school and is fired until he can get a new license from the DMV. With no job and no prospects, Otto is thrown out of his apartment and is forced to live in the Simpsons' garage until he can get his job back. Based on their mutual dislike for Homer, Patty approves Otto's new license and Otto is allowed to drive the school bus again.

Everything's coming up Milhouse when Bart's best friend falls in love with the new girl, Samantha Stanky. Bart is jealous of how much time Milhouse is spending with Samantha and plots to break them up by telling Samantha's strict father about the relationship. Samantha is packed off to Catholic school and Milhouse is heartbroken. Bart admits that it was his fault that Samantha was sent away and the two boys come to blows. Eventually they make up and go visit Samantha at her new school, where she is very happy.

Homer's half-brother Herb Powell returns, but this time not as a successful businessman. After Homer wrecked his car company, Herb has become a bum, but with a little help from Maggie, he thinks he has come up with a shoo-in invention that will put him back on top. Herb wants to build the first baby translator, a device that will interpret babies' cries and mumbles into plain speech. Homer agrees to fund the research and when Herb's business takes off, he buys Homer and the whole family lavish gifts to thank them.