This List is a few years old… Still think it’s pretty valid though.
100. The Springfield Files (Season 8): Agents Mulder and Skully visit Springfield to investigate Homer’s alien sighting, which turns out to be Mr. Burns. Lots of great gags: the Diet billboard, the reason why Burns looks like an alien, and the great use of David Duchovny and Gillian Anderson as their X-Files counterparts.
99. Who Shot Mr. Burns? (Parts 1 & 2) (Seasons 6 & 7): I never watched Dallas so I didn’t get that reference the first time I saw this episode (I was 10 years old, 1 month and 2 days old), but regardless I would be a fool not to enjoy this episode. The only 2 part Simpsons episode to date, it served as the Season Finale of Season 6 and the Premiere of Season 7 which are the best two seasons easily of this great show. Some highlights include the 104-year old Burns pretending he’s a Springfield Elementary School student, Tito Puente’s song, Marge taking the Simpson DNA with marriage, and MAGGIE being the shooter.
98. Bart the Murderer (Season 3): Bart goes to work for Fat Tony. Skinner goes missing and Bart is assumed to be guilty for murdering him. A pretty funny episode, lots of references to mafia movies. One of Wiggum’s best lines ever: “Fat Tony is a cancer on this fair city. He is the cancer and I am the… uh… what cures cancer?” By the way, Neil Patrick Harris, yes NPH, guest stars as Bart Simpson in the TV movieBlood on the Blackboard: The Bart Simpson Story.
97. Dancin’ Homer (Season 2): One of the earliest hysterical episodes. Homer becomes the mascot for the Minor League Springfield Isotopes, and moves up the ranks to join the Capital City Goofball for the Capital City Major League Team. Great moments include Homer and Burns drinking and bonding, and Homer’s Lou Gehrig’s speech parody.
96. Lisa’s Sax (Season 9): A flashback episode to Bart’s struggling to adjust to kindergarten and how Lisa got her saxophone. A nice, somewhat touching episode that showcases the family’s bond. Funny moments include Bart’s discovery of his class-clownablitiy, young big-headed Milhouse, and the Those Were the Days version by Homer and Marge.
95. Kamp Krusty (Season 4): This was originally going to be the Simpsons Movie, but they could not expand the script enough, and so it became the 4th season opener. Bart and Lisa look forward to a summer at Kamp Krusty, but instead find it torturous and horrible, prompting Bart to lead a rebellion and take over the camp. Krusty comes back in time to save the day, and makes it up to the kids by taking them to the happiest place on earth: TIAJUANA!
94. Much Apu About Nothing (Season 7): After a bear wanders into town, Homer helps to start a Bear Patrol, which raises taxes, which leads to Springfield deporting illegal immigrants including Apu, and so Homer vows to help Apu gain citizenship. Great moments: “We’re here, we’re queer! We don’t want any more bears!” And Nelson’s “Hey, German Boy! Go back to Germania!”
93. Missionary Impossible (Season 11): Homer flees PBS and becomes a missionary and fucks shit up, cause he’s Homer. Homer not believing in Jebus, hallucinogenic frogs, angry PBS debt collectors lead by Betty White and Elmo… wow, what a crazy episode.
92. They Saved Lisa’s Brain (Season 10): Lisa joins Mensa (what took so long), and soon Mensa begins to take over Springfield, but are stopped by Stephen Hawking who saves the day. Highlights include: Homer mistaking Hawking for Larry Flynt, Comic Book Guy’s C:/DOS/RUN shirt, and all of the dialog between Mensa and the dumb characters.
91. Homer Badman (Season 6): Homer grabs the Gummi Venus de Milo off the babysitter’s ass and then is branded a pervert. Classic moments include the entire candy convention, the Rock Bottom interview, and Kent Brockman speculating that Marge put the cat outside because it was harrassed.
90. Sweet Seymour Skinner’s Badasssss Song (Season 5): Skinner loses his job after Santa’s Little Helper snuck into the school vents after show and tell. Bart feels responsible and the two form a friendship that must end after Skinner gets his job back. A nice episode, its good to see Bart and Skinner being chums, its a weird dynamic to their relationship. Also Apu informing Skinner his novel is a rip-off of Jurassic Park is simply delightful.
89. Trilogy of Error (Season 12): One of their better multi-story episodes, the first act is Homer’s Day, the second act is Lisa’s Day and the final act is Bart’s day. Interesting how each story intermingles and coincides with each other. “Linguo dead?” “Linguo is dead.”
88. The Principal and the Pauper (Season 9): Apparantly Seymour Skinner is actually an impostor named Armin Tamzarian, and the real Skinner comes home to resume his old life. Everyone prefers the Tamzarian Skinner and so they get rid of the O.G. Skinner and bring back Tamzarian Skinner and declare him the one true Seymour Skinner. A nonsensical plot, but a damn funny episode.
87. Little Orphan Millie (Season 19): Luann and Kirk get back together, but go missing and are presumed dead. Milhouse becomes dark and brooding and therefore popular and his uncle comes to take care of him. One of the funniest standout episodes of the last few seasons.
86. Boy-Scoutz in the Hood (Season 5): Bart and Milhouse buy an all syrup squishee and go on a bender. When Bart wakes up he realizes he’s joined the geeky Junior Campers. He gradually accepts it, and goes on the Father-Son rafting trip with Homer and they end up lost at sea. One of the highlights is the knife safety book instructions- Don’t do what Donny Don’t does.
85. Bart Sells His Soul (Season 7): Bart sells his soul to Milhouse for five bucks, but soon realizes he made a mistake. The subplot is Moe converting the bar to a restaraunt called Uncle Moe’s Family Feedbag. How do you not like that?
84. A Tale of Two Springfields (Season 12)
: The 250th episode is also a gem. Springfield is divided into Olde and New Springfield, throw in the Who, badgers, a condescending phone company mascot. This episode also brought http://www.whatbadgerseat.com
83. E-I-E-I-(Annoyed Grunt) (Season 11): Homer sees the Poke of Zorro, goes on a dueling spree, challanges the wrong person, and flees to his old family farm, where he grows ToMacco (which is now a real hybrid plant!). This episode is great for many reasons, not only is the humor extremely wacky and zany, but there is a touch of nostolgia when they return to the home where Homer grew up. The dueling montage is classic. Glove Slap, baby!
82. Simpson Safari (Season 12): The Simpsons go to Africa and then fight diamond-smuggling chimp savers. Great Bart line: “I think we should look at her research before we condemn her entirely. (Everyone stares at him, shocked) I haven’t said anything in a while.”
81. Whacking Day (Season 4): Bart gets expelled from school, and Lisa hates the tradition of snake killing on Whacking Day. Barry White serenading snakes on the Simpson’s lawn is the natural way to save the day.
80. The Canine Mutiny (Season 8): Bart gets a credit card and buys a limited edition collie named Laddie. Laddie is practically perfect, and Santa’s Little Helper is dumber than a rock, and ultimately Bart must decide which one he really loves. A pretty funny episode with a lot of heart, its pretty much the story of a boy and his dog. A lot of great moments: Milhouse -“Remember the time he ate my goldfish? And you lied and said I never had any goldfish? Then why did I have the bowl, Bart? Why did I have the bowl?” and the credit card renaming Santa’s Little Helper as Santos L. Halper, the blind man claiming his weed was medicinal – without it he would go blinder.
79. Eternal Moonshine of the Simpson Mind (Season 19): Another recent episode, this one has Homer trying to piece together what happened the night before. As funny as it was intelligent, this episode really stands out. Easily one of the best of the last 5 seasons.
78. Home Sweet Homediddly-Dum-Doodily (Season 7): Homer and Marge are deemed unfit parents and the kids are sent to live with a foster family – the Flanderses. This episodes serves as a great juxtoposition of the neighboring families. The relative stability and boring neutrality of the Flanders House compared to the zany antics of the Simpsons makes you remember why you tune in each week to see the Simpson Family tackling a new adventure. My favorite naive Marge line ever: “The only thing I’m high on is love. Love for my son and daughters. Yes, a little LSD is all I need.”
77. The Trouble with Trillions (Season 9): Homer steals a trillion dollar bill and goes to Cuba with Burns and Smithers. I love Homer explaining how vast the government is: “You don’t know how big this government is! It goes all the way to the President!” And the IRS believing Burns has the trillion dollar bill, and based on satellite photos they know its not on the roof.
76. Homer Goes to College (Season 5): Homer has to go back to college to get his degree so he can continue working at the power plant. Funny episode that spoofs many college movies. Homer’s nerdy roommates, the prank war, the movie School of Hard Knockers, Homer classifying himself as a jock… this episode is hilarious.
75. Bart of Darkness (Season 6): The Simpsons get a pool, Bart breaks his leg and is confined to his room where he spies on his neighbors and believes that Ned killed Maude. Ok, wow, first off, whoever thought of the Pool Mobile is a genius. Martin getting all 17 layers of his swim trunks snatched, and singing solemnly at the end of the episode are two of his funniest moments. The Head of Lettuce gag, the girly Ned scream, the syncronized swimming, and did I mention the Pool Mobile?
74. Burns, Baby Burns (Season 8): Rodney Dangerfield gueststars as Burns’s son Larry. Burns tries to accept the oafish Larry, but his brash persona makes it hard. Lot of funny lines and gags, and the episode concludes with an impromptu dance party in the street.
73. Homerpalooza (Season 7): Homer tries to prove his coolness to Bart and Lisa and ends up getting shot with a cannon in a traveling freak show that tours with the Smashing Pumpkins, Sonic Youth, Peter Frampton, Cypress Hill, but each cannonball to the gut brings him closer to Jimi Hendrix. No Doubt makes an animated cameo. Homer discovering he is not “with it” because they changed what “it is” is another great moment.
72. The Day the Violence Died (Season 7): After 75 years of Itchy & Scratchy, the original inventor of Itchy, Chester J. Lampwick, comes out of bumdom with Bart’s help and Itchy & Scratchy gets cancelled. Bart and Lisa team up again to bring back their favorite cartoon, and ultimately the day is saved by Lester and Eliza, who also managed to free Apu from jail and reunite Krusty with his long lost wife. The trial scenes, the parade scene and the origin of cartoon violence are standout moments. And how can you forget the Schoolhouse Rock parody?
71. The Simpsons Spin-off Showcase (Season 8): Another 3 Story episode, this episode shows potential spin-offs like Wiggum and Skinner being P.I.s in New Orleans, Moe and a Love Machine haunted by Grampa Simpson, and the Simpsons with a replacement Lisa starring in a variety show. The sheer stupidity of each premise for a series is mindboggling, and I mean that in a great way.
70. My Sister, My Sitter (Season 8): Lisa starts babysitting, and one unfortunate night, babysits Bart. Chaos ensues. A truly funny episode focusing on an intense sibling rivalry. Bart has a knack for torturing baby sitters and to see him use his talents to torture Lisa is a real treat.
69. Lisa’s Rival (Season 6): There’s a new girl in Lisa’s class named Allison and she outshines Lisa in both academics and the saxophone. Lisa sabotages Allison’s entry for the diorama contest, but comes clean, and the girls both lose to Ralph’s Star Wars diorama. Meanwhile, Homer finds a heap of sugar.
68. Bart After Dark (Season 8): Lisa, Marge and Maggie go to help out at an oil spill at Baby Seal Beach, leaving Homer and Bart alone. Bart ends up working at a burlesque house to pay off a debt to Belle, the owner. This episode features one of the best musical numbers in Simpsons history, “We Put the Spring in Springfield!” And garbage angels? Brilliant.
67. King Size Homer (Season 7): Homer decides to get up to 300 pounds to qualify for disability so he can work at home. Enlisting Bart and Dr. Nick’s help he succeeds. Lots of funny moments poking fun at the obese, but there’s also that we-are-all-people-like-you vibe, but it doesnt get too preachy. At the conclusion, if he wasn’t fat he wouldn’t have been able to save the day.
66. Two Bad Neighbors (Season 7): George Bush (thats H.W. and not Dubya), moves into the neighborhood. Bart and Bush have a series of Dennis the Menace vs. Mr Wilson moments, but when Bush spanks Bart, Homer gets involved in one of the best prank wars in TV history. Tons of funny moments, from the block sale to Gerald Ford and Homer striking an instant bond.
65. Scenes from the Class Struggle in Springfield (Season 7): After buying a discount Chanel suit to help the economy, Marge runs into an old (rich) friend who invites her and the family to the Country Club. The Simpsons try to hide their foibles and fit in, ultimately Marge realizes that her pursuit to fit in has changed her into something she doesn’t want to be. Great line from Evelyn the rich friend: “Oh, don’t worry, Marge. Her idea of wit is nothing more than an incisive observation humorously phrased and delivered with impeccable timing.”
64. Homer the Great (Season 6): Homer joins the Stonecutters, becomes their leader and then causes everyone to quit and form the Ancient Mystic Society of No Homers. A great episode. Full of jokes about secret societies and conspiracies.
63. Homer the Vigilante (Season 5): A cat burglar terrorizes Springfield and Homer rounds up a group of citizens to patrol Springfield. Anytime Homer is in a position of leadership, hilarity ensues. Great lines: “It seems that the cat has been caught by the very person who was trying to catch him.” “How ironic.” ; “Oh my God! Underage kids drinking without a permit!”
62. Homer Loves Flanders (Season 5): Flanders invites Homer to a football game, and things go so well that Homer names Flanders his friend. Flanders can’t stand this new friendship and chaos follows. It’s great to see Homer and Flanders switching roles and Flanders being the one who can’t stand Homer. Great moments include the Nacho hat, the T2 reference, and the clock tower massacre.
61. A Star is Burns (Season 6): Uh-oh, I sense another cheap cartoon crossover… Jay Sherman from The Critic comes to Springfield to be a judge in their first film festival. Marge reluctantly puts Homer on the panel of judges, and its up to him to decide between Barney’s film, Burn’s Propaganda film, or Moleman getting hitting in the groin by a football. I hear Matt Groening hates this episode, but Simpsons fans love it.
60. The Front (Season 4): Homer never graduated from High School, so he has to get his diploma. Bart and Lisa start writing Itchy & Scratchy episodes using Grampa’s name. And then it ends with the short “The Adventures of Ned Flanders”. This is a great episode, introducing Principal Dondelinger and revealing Grampa’s name to be Abraham. Lots of good Itchy & Scratchy moments too.
59. The Simpsons Christmas Stories (Season 17): A great 3 story episode, each one with a christmas theme. A pretty funny standout from Season 17, it features a Baby Jesus story, Grampa’s feud with Santa Claus and a short using music from the nutcracker.
58. Lisa’s Substitute (Season 2): Miss Hoover gets sick, and Mr. Bergstrom (voiced by Sam Etic a.k.a. Dustin Hoffman) acts as substitute, and Lisa is quite smitten. A touching episode that deals with Homer’s failings in his relationship with Lisa, due to them having little in common. This is a heartwarming story, with a few great moments coming from Bart’s running for Class President before losing to Martin when no one votes.
57. Homer Defined (Season 3): Homer narrowly avoids disaster by randomly pushing a button. He is treated as a hero by the town, before they discover he was just lucky. Meanwhile Milhouse’s mom won’t let Bart and Milhouse hang out together anymore. It’s a funny early episode, its a glimpse of what was to come.
56. Duffless (Season 4): Homer gives up drinking for a month and Lisa tries to prove that her hamster is smarter than Bart for the science fair. Bart discovers her plan and steals her hamster, dresses him up like a pilot and sticks him in a model plane and wins First Prize. A pretty funny, often forgotten episode.
55. Treehouse of Horror (Season 2): Who knew that a simple idea like 3 scary halloween stories would become a yearly tradition? The first story is about haunted house that destroys itself rather than live with the Simpsons, the second story introduces Kang and Kodos, and the third features James Earl Jones reciting Edgar Allan Poe’s the Raven. This is another great episode from the early years.
54. Homer and Apu (Season 5): Homer causes Apu to lose his job, he takes Apu in, and tries to make things right. An all-time great moment is Homer’s line “He lied to us through song! I hate when they do that!” This episode also features the first Kwik-E-Mart, a great song, and a ton of Apu.
53. The Boy Who Knew Too Much (Season 5): Bart ditches school, witnesses a “crime”, and must decide whether or not to come forward, even if it means detention. This is a hilarious story with great bits like Skinner tracking Bart, the correct pronunciation of Chowder, and the altered boy-splattering ending to Free Willy.
52. Treehouse of Horror IV (Season 5): This features Homer making a pact with Devil Flanders, a gremlin tormenting Bart on the school bus, and a Dracula spoof. Homer not eating the last bite of his soul donut was brilliant, until he gave into his stomach.
51. Cape Feare (Season 5): Sideshow Bob is back! Again! This time the Simpsons are semi-prepared and enter the Witness Protection Program and become the Thompsons and take refuge on a houseboat. This is the first episode featuring Sideshow Bob’s other arch nemesis: garden rakes.
50. Homer at the Bat (Season 3): Homer joins the nuclear plant’s softball team, and with the help of his homemade bat takes the team to the championship. Mr. Burns wants to win and enlists the help of Jose Canseco, Don Mattingly, Ozzie Smith, Ken Griffey, Jr., Steve Sax, Daryl Strawberry, Roger Clemens, Wade Boggs, and Mike Scoscia. Great moments include the various reasons the MLB stars cant play in the game, the origin of Homer’s Wonder Bat, and Homer getting beaned to score the winning run.
49. Flaming Moe’s (Season 3): Homer invents a great drink, which Moe steals and renames the Flaming Moe. Through in a guest appearance from Aerosmith, a killer Cheers theme parody, a failed Bart crank call, and Krusty’s Non-Narkotik Kough Syrup for Kids as the secret recipe and you have a classic episode.
48. Homer vs. the Eighteenth Amendment (Season 8): Bart gets drunk (accidently) at the St. Patty’s Day parade, and as a result Springfield goes dry and starts to enforce an obscure prohibition law. Homer becomes the Beer Baron and begins to supply Springfield with booze. Rex Banner is brought in to bring down the Beer Baron, but is eventually catapulted out of town as prohibition is ended. Lots of great moments coming from the straight-edged Rex Banner dealing with the crazy and zany Springfielders.
47. Bart Gets an Elephant (Season 5): This is the one where Bart gets an elephant (obviously) from a radio station instead of ten thousand dollars. Stampy is too expensive to keep, and eventually they have to get rid of him. This episode brought us the “Where’s My Elephant” song, the first appearance of Cletus the Slack-Jawed Yokel, and Homer head-butting the Animal Refuge Ranger. Snowball II and Santa’s Little Helper walking on their hind legs saying “We love you” trying to impress the Simpsons is their funniest moment in the show’s entire run easily.
46. Lisa’s First Word (Season 4): Another flashback episode, this takes us to Bart and Lisa’s early years. As funny as it is sentimental, we learn Bart’s first word (ay carumba!), Lisa’s first word (Bart), and finally Maggie’s first word: “Daddy”. Seeing the devilish baby Bart torment a naive younger Homer is hilarious, but hearing the silent Maggie say her first word is the most memorable moment of the episode.
45. The Itchy & Scratchy & Poochie Show (Season 8): The Itchy & Scratchy Show is suffering from low ratings, so the show’s producers decide to introduce a new character: a dog named Poochie. Homer auditions for the role and lands it, but the character is not accepted and Poochie is written out. Lots of funny moments, like the mysterious teenage Roy living with the Simpsons, the kids saying they want a “realistic, down-to-earth show that’s completely off the wall and swarming with magic robots”, and Homer wondering if the cartoon would be broadcast live (the answer is no- it puts a tremendous strain on the animator’s wrist).
44. Mr. Lisa Goes to Washington (Season 3): Lisa wins an essay contest on patriotism and goes to Washington, D.C. to compete in the finals. While there Lisa discovers a corrupt official and becomes disillusioned with the government, only to have her faith restored when the corrupt official get arrested. Perhaps one of Lisa’s best episodes, the appeal of this episode stems from her reaction to the corruption and how she stands up for what she believes in, no matter the cost. This episode showcases how Lisa is easily the smartest, most complex and true to herself character in the show.
43. The Homer They Fall (Season 8): Bart gets a cool Tactical Pants-Retaining System, but Jimbo, Dolph, and Kearney beat him up and take it. Homer goes to confront their parents, and gets beaten by them, yet doesn’t fall. Moe decides to make Homer a boxer, and he quickly rises up the ranks and faces a bout with the fearsome Drederick Tatum. As Tatum beats Homer horribly, Moe rescues Homer. One of the best endings in Simpsons history: Moe using his giant fan and parachute to travel the world helping people in need.
42. Radioactive Man (Season 7): Hollywood comes to Sprinfield to film the blockbuster Radioactive Man and decide to cast a local boy as Fallout Boy. Milhouse wins the role, but decides that show business is not for him. A nice little twist as Hollywood plays the part of the naive town, and Springfield is the greedy big city. Tons of great Ranier Wolfcastle moments. Bart trying to grow an inch overnight but only growing half an inch is great. Show business is depicted as both glamorous and horrible, sometimes at the same time.
41. Lisa the Vegetarian (Season 7): Lisa bonds with a sheep, and later realizes that she can’t eat her lamb chop, nor pork chops, bacon or ham, and becomes a practicing vegetarian. Her and Homer butt heads over her choice, and she runs away from home. With a little help from Apu and Paul and Linda McCartney, she learns to accept that other people eat meat and not to be overly preachy and forgives Homer. The Flanders Family BBQ, the airborne pig, and Apu’s hidden garden are episode highlights. This is also one of the first episodes to practice continuity, as Lisa remains a vegetarian throughout the rest of the season and in every season since.
40. Team Homer (Season 7): As most diehard fans will tell you, the thing that Homer might actually be great at is bowling. In this episode Homer starts a bowling team, and Bart and Lisa have to wear school uniforms. A top fifty episode without a doubt simply because of the following Homer line: “Yeah, Moe, that team sure did suck last night! They just plain sucked! I’ve seen teams suck before, but they were the suckiest bunch of sucks that ever sucked!”
39. Homer’s Phobia (Season 8): John Waters guest stars as John, who Homer becomes friends with before realizing John is gay. Homer become worried about John’s influence on Bart, and tries to prevent Bart from becoming gay. John eventually win Homer’s acceptance, all he had to do was save Homer’s life. This is a landmark episode, not just in Simpsons history, but in TV history in general, for its depiction of a homosexual. John could have been an overly-flamboyant character, but he is not. Most of the gay jokes are not at his expense, they come from Homer’s ignorance and fear of homosexuals.
38. You Only Move Twice (Season 8): Homer gets a great new job and the family leaves Springfield for Cypress Creek. Homer’s new boss, Hank Scorpio, is actually trying to take over the world, but Homer isn’t aware of this and is doing a great job at the company. Bart, Lisa and Marge are not fitting in however, and ultimately Homer decides to take the family back home to Springfield for their sake. It’s pretty interesting to see Homer being successful and happy, while his family is miserable. Homer getting the Denver Broncos and being upset that they aren’t the Dallas Cowboys is hilarious.
37. A Milhouse Divided (Season 8): A funny, yet emotional episode about divorce. Luan and Kirk break up at a dinner party at the Simpsons. Homer begins to realize that a marriage based on routine might not be strong enough to make it last. The jokes come primarily from Kirk’s misery, his anguish at losing his wife, his job because he lost his wife. His demo “Can I Borrow a Feelin'” is based on a real album. Wow.
36. Deep Space Homer (Season 5): Homer and Barney compete for a spot aboard the space shuttle, Homer gets chosen on a technicality and goes into space. Tons of funny moments: the escaped ants on the shuttle, the inanimate carbon rod, and the Married with Children parody. Peg: “Al, let’s have sex!” Al: “Uh, no, Peg…” Al flushes toilet next to him, the audience woos and then laughs.
35. Grampa vs. Sexual Inadequacy (Season 6): Homer and Marge are having problems in the sack, and Grampa whips up a batch of his Patented Revitalizing Tonic. The tonic does wonders, and Homer and Grampa go on the road selling the tonic. In an argument Grampa tells Homer he is an accident, causing a rift between the two. The two reconcile at their old family farm, which they both burn down accidently. It is understandable why Homer fails as a father with a dad like Abe, but at the end of the day, the bond of blood is enough to overcome any argument.
34. Three Men and a Comic Book (Season 2): Bart, Milhouse and Martin buy a rare issue of Radioactive Man, but how can three boys share a single comic book? One of the really funny episodes from the early years, there is also a lot of heart in the writing which seems to be missing from the last couple of seasons. Bart selling beer for a nickel from a lemonade stand probably inspired a few idiot kids to do the same. There is also a great reference to the Wonder Years complete with voice over.
33. Homer’s Barbershop Quartet (Season 5): Another flashback episode, this one to Homer’s glory days in a barbershop quartet. Anytime you combine younger Simpsons characters with funny songs you will have a great episode. Too bad they only really tried it once. Lots of great references to the music business too.
32. The Seemingly Never-Ending Story (Season 17): Lisa tells Homer a story within a story within a story within a story (within a story). Sure it sounds complicated, but as you watch this episode you will understand why it deserves the Emmy it won. There is Mr. Burns, the Rich Texan, a bighorn sheep and a relationship between Moe and Edna, but to start to decribe the plot would ruin the story if you haven’t seen it yet. Awesome, very unique, episode.
31. Lisa’s Wedding (Season 6): Lisa goes into a fortune teller’s booth at the Renaissance Faire, and is told of her future relationship with the British Hugh Parkfield. The future in Springfield looks great with the Otto Cab Company, crying self-destructing robots, and virtual fudge. Easily the best episode that takes place in the future.
30. Behind the Laughter (Season 11): What if the Simpsons were a real family and they were just actors in a successful show? Thats the premise of this Behind the Music parody, which delves into the struggles and successes of the Simpson Family who rose to stardom with their show. This is a really self-aware show that repeatedly breaks the fourth wall.
29. ‘Round Springfield (Season 6): Bart eats a jagged metal Krusty-O and is hospitalized. While visiting him, Lisa runs into her old mentor Bleeding Gums Murphy, who is sick. He gives her some advice and his sax, and after she rocks a recital she learns that he has passed. Lisa struggles to deal with her grief and vows to make the world remember Bleeding Gums Murphy. Bart uses the $500 dollars he won in the Krusty-O trial to buy Bleeding Gums Murphy’s album for Lisa. A local jazz station plays the album and his music is heard and appreciated again. A good episode, funny at all times, but still deals with mortality and grief. The scene with Bleeding Gums and the various James Earl Joneses in the clouds is a great bit. Lisa’s last jam with Bleeding Gums is one of my favorite musical moments in the show’s run.
28. Saturdays of Thunder (Season 3): Homer realizes that he is a bad father, and attempts to reconcile this buy helping Bart build a downhill racer. The racer sucks, and Bart decides to drive Martin’s Honor Roller in order to beat Nelson in the final. Homer is hurt by this, but ultimately goes to the race to support Bart. A funny heartwarming episode with a lot of focus on the shaky father-son relationship.
27. The Simpsons 138th Episode Spectacular (Season 7): Of course you have to celebrate the monumental moments of a series, and you only get one 138th episode. It’s a little bit more than a clip show, it has deleted scenes, trivia (both real and fake), viewer mail and Troy McClure. But its essential to this list. I don’t think Dr. Marvin Monroe ever died, he just faded away.
26. Bart vs. Australia (Season 6): Bart makes a collect call to Australia and causes an international incident, and the Simpson family has to go to Australia to appologize. The humor comes from the culture clash between the Simpsons and the stereotypical Aussies. “That’s not a knife, that’s a spoon!” Who can forget the bartender who doesn’t know coffee, only beer? Bart can write really legibly on his own butt.
25. Raging Abe Simpson and his Grumbling Grandson in the Curse of the Flying Hellfish (Season 7): Grampa and Mr. Burns are the last remaining members of the Flying Hellfish, the last survivor gets a stash of stole painting taken from Germany in WW2. Bart doesn’t believe Grampa’s story at first, but eventually helps him on his quest to stop Mr. Burns from obtaining the paintings. The attempted assassinations on Grampa are hilarious, but the highlight is Grampa embarrassing Bart at school with his sheer senility.
24. I Love Lisa (Season 4): On Valentine’s Day Ralph gets no valentines, so Lisa gives him one out of pity. Ralph develops a crush on Lisa, which is not reciprocated. Ralph Wiggum is one of the funniest characters in cartoon history, and this episode is proof of that fact. Ralph. Wiggum. Ralph.
23. Homer’s Enemy (Season 8): Homer Simpson is a failure who succeeds. Frank Grimes is a success who fails. Frank Grimes (Grimey) can’t stand Homer and becomes his enemy, only to die while acting like Homer. This episode makes you realize that Homer is actually lucky, he has a life he doesn’t deserve. Grimey is the opposite, he had nothing, and had to work for everything and didn’t have anything to show for it. Grimey plays by the rules and gets punished for it, while Homer succeeds without trying. Frank Grimes is one of the all time best characters to appear in only one episode.
22. Treehouse of Horror VI (Season 7): This one features giant billboards coming to life and destroying Springfield before Paul Anka saves the day, the second story is Groundskeeper Willie as Freddy Krueger, and the final one has a computer animated 3D Homer. This episode is most memorable for the 3D Homer falling through a black hole and emerging in our real world with real live people.
21. Bart on the Road (Season 7): Bart gets a fake ID and spends his spring break by going on a road trip with Milhouse, Nelson, and Martin. Meanwhile Lisa spends her spring break with Homer, bonding with him and sharing secrets. Bart gets stranded and needs Lisa’s help to get home. Lisa asks Homer to help her, but makes Homer promise he wont reveal that Lisa told him what happened to Bart. A great episode, with far out moments like Bart delivering Big Macs to Marlon Brando’s island, and heartfelt moments like Homer and Lisa’s sleepover at the plant. The airtight alibi of Bart going to the National Grammar Rodeo in Canada is one of the best excuses of all time.
20. Bart’s Comet (Season 6): Bart has to do detention with Skinner, and discovers a comet. The comet is heading directly for Springfield, how will the town survive? A great episode, with great moments like the entire town crammed it Ned’s bomb shelter, the barnyard animal guessing game, the members of the Super Friends, and the Big Butt Skinner balloon.
19. Skinner’s Sense of Snow (Season 12): A Class 3 Kill Storm hits Springfield and Bart, Lisa and other students are trapped with Skinner and Willie in the school. This is one of those episodes with a joke every 30 seconds, each joke is a killer. The Christmas That Almost Wasn’t but Then Was, Kristi Yamaguchi, Nibbles chewing through the ball sack, Skinner slapping his Willie around… there’s too many great jokes to list.
18. The PTA Disbands (Season 6): Bart helps cause a strike at Springfield Elementary and the teachers walk out, prompting the school to hire new teachers like Jasper, Moe and Marge. Marge starts teaching Bart’s class, and he realizes he must find a way to end the strike. Bart’s antics are legendary, and his best episodes come from him causing a problem and trying to fix it. This episode is one of the best of those, because there is equal time and care in him causing the strike and ending it. Seeing Lisa freak out without school is very funny, and Grampa “helping” Jasper get his beard out of the pencil sharpener is great gag.
17. Rosebud (Season 5): Bart finds Bobo (an old teddy bear that belonged to Burns) and gives it to Maggie. Burns has been missing his Bobo which reminds him of his childhood. He tries to steal it a few times, but relents and lets Maggie keep it. She feels sorry for him and gives Bobo back to Burns. A great reference to Citizen Kane which is fitting because both Kane and Burns are based on William Randolf Hearst. The expeditions to the arctic tundra to get ice, the journey of Bobo, and Burn’s vain attempts to steal Bobo are a few great moments.
16. And Maggie Makes Three (Season 6): Yet another flashback, this one is the origin of Maggie’s birth (and Homer’s hair loss). It tells of a time before Maggie was born and Homer was free from debt, quit his job at the plant, and went to work his dream job as a pin monkey at the bowling alley. When Marge tells him she’s pregnant again, he reluctantly quits and goes back to work at the plant, but falls in love with Maggie when she grabs his finger. Marge’s line “Can we make it on a pin monkey’s salary?” is a fabulous quote, and relevant in today’s economy.
15. Two Dozen and One Greyhounds (Season 6): Santa’s Little Helper falls in love and has 25 puppies with the bitch. The 25 puppies are too much for the Simpsons to handle. Mr. Burns steals the puppies and Bart and Lisa have to figure out a way to save them. The highlight of the episode is without a doubt Mr. Burns singing “See My Vest.”
14. Marge Be Not Proud (Season 7): It’s Christmas time again, and Bart gets caught stealing at the Try-N-Save. Marge is disappointed and thinks her coddling is to blame, and begins treating Bart differently, like an adult. One of the best moments in Simpsons history: Bart puts a marshmallow in his hot chocolate. It absorbs all the hot chocolate and expands to fill the mug. Bart turns over the mug and begins to cut slices out of the mallow. Milhouse calling himself Thrillhouse is awesome.
13. Stark Raving Dad (Season 3): I just want to say that this was a favorite episode of mine for a long time, and it’s not on the list just because Michael Jackson passed and I’m jumping on the band wagon. In this episode, Homer get committed to the nut house, and meets a guy who claims to be Michael Jackson. Homer doesn’t know what Michael Jackson looks like, and so believes him and takes him home. Meanwhile, Bart forgets Lisa’s birthday and “Michael” helps Bart write a song as a present. Lisa forgives Bart and “Michael” reveals himself to be a bricklayer named Leon Kompowsky, and leaves to help more people. Michael Jackson really did guest star as himself, but credited himself as John Jay Smith. The birthday song was not really him however, but “Lisa, it’s Your Birthday” is sung on everybody named Lisa’s birthday at least twice.
12. Marge vs. the Monorail (Season 4): One of the first really crazy plots came from the brain of Conan O’Brien. A con man comes to town and convince the townsfolk to build a monorail, but Lyle Lanley instead takes the money and builds a shoddy system. Homer gets a job conducting the train and its speeds out of control on the track until Homer makes an anchor and manages to stop the train. Great moments include the “Monorail” song, Leonard Nimoy, and Bitey the Possum.
11. Itchy & Scratchy Land (Season 6): The Simpsons go on vacation to Itchy & Scratchy Land, where nothing can possably go wrong, uh, possibly, go wrong, and of course the automated robots go crazy and ruin the vacation. Why its funny: great jabs at Disney, Bort, and the Simpson’s road trip.
10. El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)(Season 8): Homer eats too many Guatmala insanity peppers and has a trippy fantasy with turtle guides and talking space coyotes, and realizes that Marge might not be his soul mate. This episode stands out with its far out animation, Johnny Cash as the Space Coyote, and the scenes at the Chili Cook-off (where Homer acts like the Pope of Chilitown). Also very poignant at the end when you realize that maybe Marge and Homer are truly soul mates.
9. Mr. Plow (Season 4): “Call Mr. Plow, that’s my name. That name again is Mr. Plow.” That’s a jingle. Homer gets a plow, Barney gets a better one, Homer almost kills Barney, Homer saves Barney, Homer insults God, God melts the snow, Mr. Plow has no business.
8. Homie the Clown (Season 6): Homer sees a billboard for Krusty the Klown’s Klown Kollege and becomes a clown. He impersonates Krusty a bit too much, and Fat Tony kidnaps him thinking he’s Krusty. The bicycle riding scene with Krusty and Homer is a classic cartoon squence. Homer’s daydreams about clown college are among his best.
7. 22 Short Films About Springfield (Season 7): This show has a huge supporting cast of oddball Springfielders, and this episode features a bunch of them: Skinner and Chalmers, Burns and Smithers, Nelson and the Very Tall Man, Bumblebee Man, Dr. Nick, Prof. Frink and many more. All the stories weave in and out of another and it’s a very well rounded and random episode.
6. Treehouse of Horror V (Season 6): The best Treehouse of Horror episode. The first story is “The Shinning”, a parody of The Shining. “No TV and No Beer Make Homer Go Crazy.” The second story is about Homer’s time traveling toaster. The third is about Springfield Elementary killing kids and serving them in the cafeteria. Homer time traveling is the best Treehouse of Horror short easily.
5. Mountain of Madness (Season 8): Homer and Burns are teamed up on a company retreat to Mt. Useful, and end up stuck together in a cabin after an avalanche buries them. Burns and Homer’s progressive slide into insanity is topped off by turning the cabin into a rocket house that speeds down the mountain. Bart and Lisa teaming up with Smithers is hilarious. A funny gag is Marge realizing shes holding Maggie upside down. “Only Who can prevent forest fires? You said ‘You’, referring to me, which is incorrect. The correct answer is ‘Only You can prevent forest fires.'”
4. Last Exit to Springfield (Season 4): Homer become the Union Leader at the plant, Burns takes away the dental plan, just when Lisa needs braces. The workers go on strike, Burns turns off the power, but eventually gives in and reinstates the dental plan. “Dental plan! Lisa needs braces!” Comparing Burns to the Grinch is genius. This episode has been number one on a few critic’s lists. It’s a really funny, genuinely smart episode.
3. Homer the Heretic (Season 4): Very few shows can handle religion in a comedic way and still raise debate and inspire one to rethink their own beliefs. One Sunday, Homer decides to stay home while Marge and the kids go to work. He has the best day of his life and decides to stop going to church. This episode pokes fun at many religions, mainly christianity, but also Judaism, Hinduism etc. There are also so many great jokes in this episode, and Homer’s dream conversation with God was brilliant. You get bonus points if you notice God has five fingers.
2. Lisa on Ice (Season 6): It’s a classic episode, a favorite of many. Lisa and Bart take an intense sibling rivalry to the ice as their two hockey teams are set to play each other in a game. Ralph’s line “Me fail English? That’s unpossible” is quite possible his most quoted line. Lisa’s transformation into a tough jock and Bart’s equal on the ice is fun to watch. This is one the funniest sport themed episodes in the history of television. And it ends with Bart and Lisa being all wholesome and loving, a good way to remind you that no matter what, they are still family at the end of the day.
And the number one episode is Lemon of Troy (Season 6): This is a perfect episode in every single way. First off, everything comes full circle: in the beginning Bart sees a “Wet Cement” sign and he sees on again towards the end. You also see Frink’s flying motorcycle twice, and roman numerals twice. It’s a great story about town pride, kids being kids, and the art of war. Every 30 seconds theres a joke, and every joke is hysterical. The episode starts with a bang, every act is solid, every joke memorable. How can you forget the strange yellow, lemon shaped rock? Or Shelby and the other kids from Shelbyville? The story of how Jebediah Springfield and Shelbyville Manhattan founded their respective towns is funny. I love Bart’s raid on Shelbyville with Milhouse, Nelson, Martin, Todd, and Database and them reacting to the subtle differences between the towns. Marge’s speech about Springfield, Bart’s vision of the future, the escape from the man-eating tigers, this episode is so full of jokes and gags it boggles the mind. This is the BEST episode, I’ve said it before, and I’ll say it again, it is a perfect episode.
Critically Rated at 15/17
Written, Rated, and Reviewed by Brendan H. Young