#10 – ‘Viva Ned Flanders’
Season 10 – Episode 10 (Episode 213 Overall)
Synopsis – When Ned Flanders reveals that he is 60 years old and looks young because he has done nothing exciting in his life, Homer decides to take him to Las Vegas, where, after a night of drunken partying, they end up married to two derelict barmaids.
#9 – ‘Life On The Fast Lane’
Season 1 – Episode 9 (Episode 9 Overall)
Synopsis – Having forgotten about Marge’s birthday, Homer rushes to the Springfield mall and impulsively buys her a bowling ball. Marge is not impressed with the gift and after discovering that he intends to use it, she decides to spite him by going bowling herself. While at the alley, she meets Jacques, a charming French bowling instructor, who offers her lessons. Jacques begins to fall for Marge and Marge undergoes a moral dilemma.
#8 – ‘Behind The Laughter’
Season 11 – Episode 22 (Episode 248 Overall)
Synopsis – 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.
#7 – ‘Itchy and Scratchy Land’
Season 6 – Episode 4 (Episode 107 Overall)
Synopsis – Bart and Lisa convince their parents to take their family vacation at the newly opened Itchy and Scratchy Land. The vacation seems to be going well, until Bart and Homer are both apprehended by the park security for assaulting a staff member dressed in an Itchy suit. Professor Frink realizes that all of the park’s Itchy & Scratchy robots will turn on their masters; an event which proves true as a horde of Itchy and Scratchy robots advance on the Simpsons.
#6 – ‘Marge vs. The Monorail’
Season 4 – Episode 12 (Episode 71 Overall)
Synopsis – After Mr. Burns is caught storing his excess nuclear waste inside Springfield Park’s trees, he is ordered to pay the town $3 million. The town is originally set to use the money to fix Main Street, but the charismatic Lyle Lanley interrupts and convinces the town to use the money to buy one of his monorails.
#5 – ‘The City Of New York vs. Homer Simpson’
Season 9 – Episode 1 (Episode 179 Overall)
Synopsis – Homer allows Barney to use his car when Barney is picked to be the designated driver for that night at Moe’s Tavern. However, Barney disappears for two months with the car and returns without it. Homer searches for his car and eventually receives a letter from the City of New York. The family is excited to go there to obtain the car, but Homer, who had a bad experience in New York when he was younger, is reluctant.
#4 – ‘You Only Move Twice’
Season 8 – Episode 2 (Episode 155 Overall)
Synopsis – When Homer accepts a new job at the Globex Corporation, the Simpson family moves to Cypress Creek. Homer enjoys his new work and his easy-going boss, but is completely unaware that his boss is an evil genius and that the company is a vehicle for international extortion. The rest of the family have trouble settling in Cypress Creek and Homer must make a choice between Cypress Creek and Springfield.
#3 – ‘Selma’s Choice’
Season 4 – Episode 13 (Episode 72 Overall)
Synopsis – Marge’s Great Aunt Gladys Bouvier dies and the Simpsons, Patty, and Selma attend her funeral. During the reading of her video will, Gladys tells Patty and Selma not to die lonely and miserable like she did. Though Patty doesn’t care, Selma decides that she wants a baby. Meanwhile, Homer eats a spoiled hoagie, and becomes dreadfully ill. As a result, he can not fulfill his promise of taking Bart and Lisa to Duff Gardens and Selma agrees to take them instead.
#2 – ‘Colonel Homer’
Season 3 – Episode 20 (Episode 55 Overall)
Synopsis – After Homer’s behavior at the movie theater embarrasses Marge, they have a large argument, causing Homer to head to a redneck bar where he meets a beautiful barmaid named Lurleen Lumpkin with a talent for singing. Homer becomes her manager and does everything he can to make Lurleen famous, but it takes a very long time for him to notice Lurleen has fallen in love with him. With Marge already upset and thinking Homer’s the one with the roving eyes, it’s time for him to decide on his romantic future.
#1 – ‘Last Exit To Springfield’ – READ THIS!
Season 4 – Episode 17 (Episode 76 Overall)
Synopsis – After learning that Mr. Burns’ decision to revoke their dental plan has coincided with Lisa needing braces, Homer convinces his coworkers not to give up their dental plan and becomes the new head of the workers union at the Springfield Nuclear Power Plant. He holds talks with Mr. Burns, but these go badly because Homer is not intelligent enough to understand Burns’ sly innuendos. The plant goes on strike and Mr. Burns decides to take away the electricity for the entire town. However, this encourages the workers union and Burns decides to reach a deal with Homer.