Since they first appeared in sketch format on The Tracey Ullman Show in 1987, The Simpsons have become arguably the most successful animated show of all time, holding the record for longest-running American-sitcom and longest-running American scripted primetime television series. Homer, Marge, Bart, Lisa, and Maggie have been a part of television viewer’s lives for decades now, many of whom have grown up watching the distinct yellow family through all their victories and follies.
Every character, every iconic Springfield location, every storyline, and every gag the show has pulled out of its hat has been an important building block for television, comedy, and animation as a whole. Many fans consider the first ten seasons to be the “golden age,” notable for the sharp writing, heart-warming plots, and innovative humor that makes The Simpsons so treasured.
10 Season One: Krusty Gets Busted
Krusty is an oddball character, but he is still Bart’s hero. While television’s favorite clown is no stranger to controversy, the lovable celebrity finds himself in hot water when he is accused of robbing the Kwik-E-Mart. It’s up to Bart and Lisa to prove the innocence of their favorite TV prankster, putting them at odds with Krusty’s eloquent co-host, Sideshow Bob.
What makes this episode a classic is its status as the origin of the Bart/Sideshow Bob feud that continues to be an instrumental part of the show. Considered a milestone in the more absurd category of humor the show is best known for, this episode is also marked by its hilarious dialogue and the first appearance of anchorman, Kent Brockman.
9 Season Two: Oh Brother, Where Art Thou?
Homer is one of those lovable buffoons who can’t seem to go an entire episode without making a mockery of himself. In this prominent episode from season two, Homer learns he has a long-lost brother named Herb (voiced by Danny DeVito) who is a successful owner of an automobile developer.
The Simpson clan gets a taste of the luxury lifestyle when they go to visit him, but things get out of control when Herb recruits Homer to design a new car for the “average American man.” Notable for Homer’s hilarious car design and Danny DeVito’s terrific performance, this classic showcases how the tiny details of each episode can bring out the best in the show.
8 Season Three: Homer At The Bat
The Simpsons are notorious for their star-studded guest cameos, in fact, it has become something of a rite of passage for many celebrities. Although arguments can be made whether this is a good thing for the show, there is no denying that when done well, guest stars add something special. In this hilarious episode, Mr. Burns hires a medley of real-life baseball sluggers to play for his powerplant’s baseball team (featuring Wade Boggs, Darryl Strawberry, and Ken Griffey Jr all voicing themselves).
By making complete use of their star power through brilliant sight gags (including Wade Boggs getting into a fight with Barney over who was the best British prime minister and Steve Sax being arrested for every unsolved murder in New York City), The Simpsons proves that visual humor is an essential part of the show.
7 Season Four: Marge Vs. The Monorail
It might be an obvious choice, but it’s hard to argue against one of the most masterfully crafted episodes of TV ever. This is a Simpsons episode with everything a fan could want: Phil Hartman as a cheeky con artist, Homer wearing a ridiculous caped costume, an iconic musical number, and even Leonard Nimoy!
“Marge Vs. The Monorail” is peak The Simpsons. Featuring a brilliant script written by none other than Conan O’Brien, the episode contains some of the funniest lines in the whole show (“I call the big one, Bitey”). It’s beyond impressive just how many jokes they can fit into such a short running time, and the animators are at the top of their game in this masterpiece episode starring Marge as the lone voice of reason against Springfield’s desire to have a shady charlatan build them a monorail.
6 Season Five: Cape Feare
The history of Bart and Sideshow Bob is one of the greatest rivalries in syndicated history. Sideshow Bob is the perfect deceptively charming villain to Bart’s lovable trickster character, perhaps best exemplified in this essential episode.
A satire of Cape Fear, Sideshow Bob is released from prison and proceeds to terrorize the Simpson clan through his usual antics, driving them to join the Witness Protection Agency and seek refuge on a houseboat. Filled with classic gags ranging from Bob’s continuous “step on a rake” bit to Homer’s inability to grasp his new name, this is an episode worth watching again and again.
5 Season Six: Treehouse Of Horror V
“No TV and no beer make Homer something something.” The “Treehouse of Horror” series is a long-standing Halloween tradition that sends the beloved characters into three ghastly and morbid stories. The fifth rendition is a memorable hodge-podge of satire and scares, starring a spoof of the classic Stephen King horror book and film, The Shining, an alternative universe sci-fi escapade, and a grisly war between Springfield Elementary students and a pack of vicious cannibal teachers.
The writers and animators ramp up the violence in these three tales, but they also ramp up the humor and pop culture references. From Homer’s hilarious descent into madness to Groundskeeper Willie’s multiple death scenes, this is one of the most enduring “Treehouse of Horror” episodes ever.
4 Season Seven: 22 Short Films About Springfield
One of the most engaging and remarkable aspects of The Simpsons is their use of outlandish storytelling. Plots start in one interval of space before jumping into a completely different story in a short period of time. Countless television shows have taken influence from The Simpsons unconventional narratives, but few other series have gotten as experimental as this singular episode.
An impressive feat of fitting in as many interconnected stories and characters as possible (à la Pulp Fiction), 22 Short Films is a tour de force for The Simpsons writers. This episode is still highly regarded among fans and is considered a cult classic for its steamed hams memes.
3 Season Eight: You Only Move Twice
This essential episode from season eight is one of the highlights of the entire show thanks to its unforgettable one-time character, Hank Scorpio (voiced by the brilliant Albert Brooks). Homer gets a new job in a Silicon Valley-esque community at a swanky company run by goofball owner, Scorpio.
While his family adjusts to a fresh start, Homer receives a warm welcome from his new boss who takes a shine to him. Unbeknownst to Homer, Scorpio is actually a pseudo-James Bond villain with plans for world domination. The contrast of Scorpio’s carefree demeanor and his thirst for evil is hilarious and Homer’s inadvertent assistance in aiding him is a riot. The dialogue is amazing, the story is engaging, and the references to the James Bond films are exceptional.
2 Season Nine: The City Of New York Vs. Homer Simpson
The Simpson family has a penchant for traveling to exotic locations, but what makes this episode work so well is that their trip to New York City is a complete failure. Homer’s car gets clamped in the city after Barney takes it for a joy ride and the family has to visit The Big Apple to retrieve it.
Naturally, the episode is filled with cameos, references to the city and its inhabitants, and Homer struggling to remain sane. And crab juice, lots and lots of crab juice.
1 Season Ten: Viva Ned Flanders
Ned Flanders is best known as The Simpson’s lovable religious neighbor, but in this episode, he cuts loose for once and joins Homer on a gambling trip to Las Vegas.
Naturally, it ends with them both hitting rock bottom and accidentally marrying two cocktail waitresses (much like The Hangover). It’s refreshing to see Ned let down his hair and have fun with Homer, even if it is somewhat destructive.
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