20. Brick Like Me: The Simpsons has toyed with non-2D storytelling techniques early on, as seen with Homer's 3D misadventure in "Treehouse of Horror VI." Even though a puppet-ed version of the Simpson family proved to be harmonious alongside a live action Katy Perry in "The Fight Before Christmas," the show truly leapt off the drawing board with the recent LEGO themed episode, "Brick Like Me." Feared by fans as just a cash in to promote The Simpsons LEGO sets Brick Like Me" built a solid comedic plot foundation on Homer's journey into the fantasy brick world, while still holding that keen Simpsons knack for self-deprecating humor, comically noting the similarities of The Lego Movie to the Homer's storyline. "Brick Like Me" proved The Simpsons still knows its way around the funny block.
19. Deep Space Homer: You probably only need one line from this episode to justify its place in the top 20, and in this Iconic farce, NASA’s ratings as well as their funding is going down the toilet, so they decide to find the everyman to send up into space to get more viewers. The results are Barney and Homer, resulting in every kind of joke you can imagine out of these two. Drunk jokes, Exercise jokes, Movie jokes, They even got Buzz Aldrin one of the first men on the moon to guest star. that alone is enough to sell the episode. there’s even a copy for real astronauts to watch aboard the International Space Station.
18. A Fish Called Selma: Ever want to see a Planet of the Apes musical, now here's your chance. After his rumored relationship with sea-creatures tanked his career, Troy McClure takes the advice of his agent – played by Jeff Goldblum – and tries resurrecting his reputation by marrying Selma. This episode reminds us that “The Simpsons” is successful thanks to its main cast, but also its stable of stellar minor characters – and Troy McClure finally gets the top billing he deserves.
17. Behind The Laughter: Skewering the critically acclaimed VH1 series docudrama series Behind the Music, “Behind the Laughter" gave a facetious fictional account of The Simpsons’ not-so-humble origins. Even the most devoted fans were surprised to learn about Homer’s passion for cleaning recording booth consoles, and we were shocked to hear about Lisa’s growth scandal that producers used keep her young. Who knew that the one responsible for reuniting the funny family was country-music icon and hard-partying fratboy Willie Nelson? Of course it was fake, but this mocking of a cherished documentary series was Simpsons satire at its finest.
16. Lisa's Wedding: Of all the future episode entry That The Simpsons installments in general. “Lisa’s Wedding" is much more touching and endearing, displaying Lisa’s love for her family despite their occasional embarrassing actions. The episode’s take on the future is realistic but also comical, giving nod to the eventual 40 classic films starring Jim Carrey and the eventual transformation of FOX into a hardcore sex channel. Plus Lisa’s fiance Hugh Parkfield is likable and realistic in his love for Lisa but also in his resentment of the family, especially Homer’s swine bride and groom cufflinks.
15. Homer's Enemy:This is one of the darkest “The Simpsons” Episodes. And I’m not gonna lie, that’s what makes it so enjoyable. Mr. Burns hires a hard working individual named Frank Grimes who despite his genius mind who gets no breaks in life, always met with nothing but misfortunes, and never had anything handed to him. On his first day on the job he meets Homer Simpson, obviously the exact opposite. Everything was handed to him questionably, he has no idea about sacrifice, and is as dumb as…well, Homer Simpson. Grimey develops an intense hatred for Homer because he can't except the fact such a man is allowed to exist, and wants to prove to Homer the world and himself that life doesn't go that way. We all gotta take responsibility and face the consequences of our actions. But Homer’s actions constantly have no punishment. (Beat) Actually, they do, except it’s often given to Grimey. Homer tries to get Grimey to Bury the hatchet by inviting him over for dinner with his family but it only makes Griemy even more bitter, as he attempts to expose Homer for the fraud that he is but fails miserably. Again, they could’ve just made Grimes just the straight-up bad guy, but deep down inside you sympathize with him, he's like a real person who was dropped into the world of The Simpsons, and had to deal with a character like Homer, and if I was in his shoes I' too would end up have a mental breakdown that would get myself killed.
14. A Star is Burns: A great Simpsons classic that perfectly satirizes Hollywood and filmmaking as a whole, Springfield decides to take one of Marge's suggestions on attracting more tourists and run a film festival and the Simpsons suggest Jay Sherman of the Critic be the host. But Mr. Burns as well as everyone else is determined to win at all coasts. it had the best Barney Gumble moment plus 5 words Man-Getting-Hit-By-Football.
13. Bart Gets an Elephant Speaking of silly, there’s not a lot of emotional heft to “Bart Gets an Elephant,” the tale of a boy and his jerk of an elephant. But the journey is great. And the time Bart and Stampy and the family spend together is great. Even the coda at the wildlife reserve is great, because it involves Homer repeatedly headbutting a guy in the ribs. There’s a smart joke about how we can’t be sure what’s right today “what with all our modern ideas… and products!” but there’s also a great bit where Barney is pulled out of a tar pit and lights himself on fire. He’s mildly annoyed. So, you see, there’s something for everybody.
12. Homer the Great: Ever fantasize about a secret world where people get more privliges then the common man? so do the Simpsons. Homer stumbles across an ancient order of the Stonecutters, an organization that really doesn’t do anything except keep secrets and reward itself. When he learns that his dad was one of them He manages to get in in the most hilarious initiation test ever. Unfortunately he gets in big trouble when he accidentally destroys their sacred parchment. That’s also pretty funny. They discover a birthmark on him, though, that he is the Chosen One, sent to bring balance to the Stonecutters. And he, of course, abuses the power like mad.but let’s just say it’s a perfect bookend to a perfect joke, and a clear sign of how stupid and immature the whole idea of privilege organizations can be. It’s another one of those that just has great joke after great joke, many of them ranging from very creative to just bizarre.
11. Marge Not be Proud: Like the “Treehouse of Horror" series, The Simpsons had regularly done a holiday-themed episode as December rolled around, Heck their first episode was a Christmas episode. But the most celebratory of which is “Marge Be Not Proud." Focusing on Bart’s inner turmoil after shoplifting a Bonestorm video game, it was a touching sentiment to see Bart redeem himself and his family after being disgraced by the local Try-n-Save store. It wasn’t the most typical Christmas episode, but “Marge Be Not Proud" was a welcome Holiday gift to audiences at home, even if "Lee Carvallo’s Putting Challenge" wasn’t.
10. The Springfield Files: It's a little trans FOX Crossover when X-Files own FBI Mulder (Voiced By David Duchovny) and Scully (Gillian Anderson) visit Springfield to investigate Homer's alien sighting after 10 beers. Leonard Nimoy returns to the series to narrate this episode only to dismiss himself early leaving the squeeky voiced teen to finish it.
9. 22 Shorts about Springfield: As the series evolved, more and more of the Simpsons spotlight was shared with the town’s supporting cast. And as Krusty the Clown, Apu, Moe, Smithers, Principal Skinner and many other secondary residents got big close-ups in their own episodes, the best minor character vehicle was “22 Short Films About Springfield." Detailing the rambunctious exploits of the town that very few residents see, the short form stories were taut and innovative, capitalizing on the writers’ ability to create big laughs even in small timeframes. The best segment is easily Skinner’s attempts to earn Superintendent Chalmer’s good will with “steamed hams" as his house begins to burn down. (Bonus points for the episode’s criminally good Pulp Fiction references.)
8. Marge vs The Monorail: Written by Conan O’Brien, this is another episode that’s high on the hilarity, Hartman and song scales . Springfield comes into a ton of money, and there’s a town meeting held about what to do with it. A Smooth talking Con artist named Lyle Lanley tricks them into building a Monorail using cheap faulty parts while he keeps the rest of the money for himself. Again, this leads to a lot of great possibilities, like Homer being the conductor, all of the characters getting onboard, discovering what happened to the original monorail, even somehow working Leonard Nimoy into one of his strangest cameos. “Marge vs. the Monorail” ranks high when it comes to absurdity – just the way we likes it.
7. Cape Feare: We defy you to find a peripheral character as beloved as Sideshow Bob. With Kelsey Grammer providing his dulcet tones, the series takes on a “Cape Fear” parody with almost shot-for-shot precision, as this was the first time he didn’t have a diabolical scheme for power lined up, instead just wanted straight-up vengeance on his nemesis Bart Simpson. It was actually one of the first times you saw Bart in real peril, like someone was actually trying to murder him, and it came from the perfect person you’d want to see try to murder him. I guess from that angle, it’s pretty cool. The Simpson family ends up in Witness Protection, living on a houseboat. Between the singing, Grandpa gag, cacti and rakes, I still can’t pick a favorite part.
6. You Only Move Twice: Homer gets hired by a company called Globex but he's oblivious by the fact that his new laied back boss err supervisor Hank Scorpio is a megalomaniac hellbent on world domination. this episode sees the family follow Homer’s new job to Cyprus Creek. And of course, each member hates it for completely distinct and hilarious reasons. Plus, we get to see Homer succeed – however unwittingly – and that just makes us smile.
5. Who Shot Mr. Burns: Even “The Simpsons” caught cliffhanger fever; but to date this remains their only two-parter. Spoofing “Twin Peaks” and “Dallas,” the folks of Springfield tackled an attempted-murder mystery. After terrorizing the town in increasingly wicked ways, Mr. Burns is shot by an unknown attacker. Every Springfieldian has a motive – From Smithers, Groundskeeper Willie, Moe, Barney, Lisa, Skinner, Homer, Bart, hell even guest star Tito Puente. Where as Part 1 shows what a heartless Bastard Mr.Burns is Part 2 plays the part of a murder mystery but despite clues and a contest, not one viewer guessed correctly. Neither did Chief Wiggum.
4. Homer At The Bat: In terms of guest voice-overs, this episode may not have the biggest star power anymore, thanks to appearances from the likes of Tony Blair and J.K. Rowling in later episodes, but it is one of the best uses of guest stars, but still doesn't take away the focus of the episode, and in this case it's Homer playing Softball. Mr. Burns starts a softball team to which Homer seems to do surprisingly well with, all because of what he claims is his magic bat. But once Burns makes a million dollar bet with another power plant team, the game is on to cheat like nobody’s cheated before. He gets some of the greatest baseball players of all time on his side and forms the ultimate superforce. What makes this episode so good is not only the writing, but also the fact that they actually got these players to do the voices. They even managed to give a lot of them sort of comedic personalities, like Darryl Strawberry’s a boot-kisser, Steve Sax is a beat, and Ozzie Smith is trustingly naïve. Even with all these people to juggle, though, they still keep the focus on Homer, never losing track that is still his story.Plus, y’can’t top the ridiculous things that happen to the players to make them miss the game.
3. The City OF New York VS Homer Simpson: The Simpson family has taken many domestic road-trips throughout the course of the series. But the biggest U.S. adventure was Homer’s hesitant journey to the Big Apple. After discovering Barney drunkenly left his car illegally parked at the World Trade Plaza, Homer must battle against the sleazy forces of New York to get it back, while his family partakes in the finer amenities of the city. The episode was briefly unaired in the wake of the 9/11 terrorist attacks, but now it’s been welcomed again as a homegrown Simpsons classic.
2. Treehouse of Horror V: Arguably the best Treehouse of horror episode to this day, this Halloween special includes a parody of the Shining where the family house sits for Mr. Burns only for Homer to go berserk and attempt to murder his family, Homer unwittingly wrecking the space time continuum to fix the toaster, and Principal Skinner creating a new lunch entree the kids of Springfield elementary. Plus Willie the Groundskeeper’s continuous axe-related murders and the clever, skinless parody of “A Chorus Line" was unexpected but full of heart. “No “Treehouse of Horror" tale was quite as satirically and satanically biting so much as its fifth installment.
1. Last Exit to Springfield: Absurd Humor meets social issues When Homer is elected head of the Nuclear Plant’s workers’ union, and Mr. Burns – acting characteristically Grinch-like – revokes their dental plan. This is a pretty epic episode in terms of scope, with several memorable moments etched in the show’s iconography. With Lisa’s dentist serving as an episode highlight, “Last Exit to Springfield” is relevant, irreverent, satirical, and perfect.