Life on the Fast Lane
(Season 1, Episode 9)
The Simpsons' introductory season has a charming rough around the edges feel, with obvious signs of the show's writers and animators figuring things out. Its best episode focuses on Marge as she's predictably let down by Homer, who forgets her birthday and thoughtlessly buys himself a bowling ball and puts in forward as Marge's gift. Out of spite Marge decides to go bowling and encounters a slimy, but charming French bowling instructor. The pair begin to fall for eachother over repeated encounters and it leads Marge to a (literally depicted) crossroads in her life.
This is a very early example of the show balancing jokes with real emotional depth for the characters. It tackles Marge and Homer's turbulent marriage in a grounded and mature fashion. Even if the way it wraps itself up feels a bit too clean considering the stakes put forth, it's still a heartfelt and assured finish. Albert Brooks guest stars as Jacques and is very memorable, combining passionate suave with a slimy edge. It doesn't shy away from showing the impact of this marriage crisis on the kids and has a smartly balances the serious with the sardonic.
While season 1 of The Simpsons always feels like it's still finding its footing, the confident portrayals of its characters on display here feels way ahead of the curve and in such makes it an essential episode.
Bart Gets an "F"
(Season 2, Episode 1)
The opening episode of The Simpson's sophmore season capitalised on what was dubbed "bartmania" at the time in the early '90s, as the troublemaking Bart Simpson was an instant star. While they could've played the hits with what had already sent this cartoon character to the stratosphere in the public eye, Bart Gets an "F" presents a wonderfully nuanced exploration of his character.
This episodes sees Bart continuously trying to worm his way out of his various school work assignments, but his teacher Mrs. Krabappel is having none of it and it is recommended that Bart has to improve his grades or he will have to repeat grade four. This leads Bart to finally make an effort in order to salvage his school year.
Here, Bart Simpson is presented at his most vulnerable. His 'too cool for school' attitude is torn away when he is backed into a corner. He makes a genuine journey to change his mindset, only for it to not be enough - even though he sacrifices a vibrant snow day in order to study for his test. His desperation feels real and relateable in that regard. Seeing
him fail at the end regardless feels heartbreaking and is one of The Simpsons best, most genuine emotional pulls. His rivalry with his teacher feels genuine too, Mrs. Krabappel wouldn't be fully developed until later in the show's run, but here her playful nature and genuine wish for Bart's success is shown in a great way.
It's one of The Simpsons most honest episodes and features a fantastic mix of humour & characterisation.
Itchy & Scratchy & Marge
(Season 2, Episode 9)
In the 1990s the issue of media being too violent, vulgar or inappropriate for children was a hot topic. Of course The Simpsons being so ever-present in the pop-monoculture meant it was a key target, especially given Bart Simpson's popularity, his suitability as a role model was often called into question.
Itchy & Scratchy & Marge is an episode which directly explores the issue of censorship within the universe of The Simpsons itself.
Marge Simpson takes issue with the kids watching The Itchy & Scratchy show, which baby Maggie seems to imitate. She sets up a protest group to take the program off the air which gains enough support for the network to remove the violence from the show and instead fields schmaltzy, humourless cartoon adventures, which the children dislike and abandon watching to play outside. As Marge's protest group achieves success, they move onto boycotting a nationwide tour of Michelangelo's David sculpture (due to its nudity), which causes Marge to reassess her movement given that she appreciates the artistry of the sculpture.
While other cartoons would lampoon the '80s-'90s panic over violent and vulgar media (see: the South Park movie from 1999 which went big with this idea), The Simpsons offers a more balanced view of the situation. Marge is not wrong to challenge the hilariously senseless violence that makes The Itchy & Scratchy Show one the The Simpsons' best running gags, but when she realises her hypocrisy in how she feels about banning the David sculpture, it cements the issue as open-ended. With a run of great gags, including the juxtaposition of the violent Itchy & Scratchy cartoons with the extremely sterile non-violent ones, it makes for an easy highlight.
One Fish, Two Fish, Blowfish, Blue Fish
(Season 2, Episode 11)
This episode is an early Homer focused highlight, balancing his usual dumb wrecking ball shenanigans with a heavy topic. Sure, nobody watches this and believes that Homer will die at the end of the episode, but they take the idea seriously enough in the plot to lead to some good emotional beats landing.
Homer eats some toxic sushi and is informed he has less than 24 hours to live! SO he makes a bucket list and the Simpsons family and friends try to help Homer achieve these goals. Including reconciling with Grampa, making a video for Maggie when she grows up and sticking it to Mr. Burns.
It's an enjoyably vulnerable look at Homer Simpson, a character who's often not somebody we directly empathise with due to his rampant stupidity and tendencies to act like a jerk. It was smart to choose Homer to be the focal point of such a plot, since he's a bit too dim-witted to fully grasp the situation and in such it's still a pretty light episode even though it's directly confronting death. It gives a little empathetic tour of Homer's various relationships across his family and Springfield, while having some nice jokes as well as the expected emotional beats. They end it with a sequence of great gags to finish with some levity as well.
Lisa's Substitute
(Season 2, Episode 19)
Lisa Simpson really comes into her own in The Simpsons second season and the episode Lisa's Substitute is for sure the highlight of her character development. This episode is packed with great character depth and smartly tackles themes of social & emotional alienation that a lot of gifted children experience. It feels like a great mirror episode to Bart Gets an "F" in that regard.
Lisa's class gains a substitute teacher in the form of Mr. Bergstrom, who has some oddball teaching methods and a passion for helping out the young students that immediately strikes a chord with Lisa. Homer and Lisa encounter Mr. Bergstrom outside of school and he tells Homer that he needs to be a more positive role model to help with Lisa's development. However, since he is a substitute teacher, Lisa's time being taught by Mr. Bergstrom has a fast approaching expiry date, eventually leading to her despair and a heartwarming farewell.
I love the character of Mr. Bergstrom and what he represents to Lisa. Sometimes it's nice to not have any big twist or betrayal and just have a good-hearted character who only wants the best for others. It highlights how the system as a whole is failing Lisa when he has to leave, but his impact is enough to invite some positive change in the paternal relationship between Homer and Lisa.
There's a low-stakes b-plot involving Bart running for class president which breaks up the core storyline in a nice way, never taking too much attention away and providing the laughs when they aren't as frequently offered in the core plot. Dustin Hoffman lends his voice to Mr. Bergstrom and they pack in a quick The Graduate gag involving him which is great. This is a deceptively simple episode that ends up one of the most effective episodes by a mile.
Bart the Murderer
(Season 3, Episode 4)
Bart the Murderer for me is the episode where it's cemented that The Simpsons were on a winning run. It's where the mix of funny jokes with genuine emotional pulls and characterisation really hit the sweet spot. Pacing is fast and it rewards repeat viewings with how densely packed the episode is with character and gags. This is another wonderful Bart focused episode, but also one where the town of Springfield and its growing cast of characters come together in a great way.
This episode sees the introduction of Fat Tony and his mobsters, when Bart's already dismal day at school is made worse when he accidentally skateboards down into the Tony's mob lair. However, Bart becomes an asset to Tony's gang enterprise as they use him for part-time work and as a general errand boy. Though his involvement starts getting questionable after the mobsters confront Principal Skinner after he keeps Bart behind at school, leading to him being late for his part-time work. Skinner goes missing and Bart is taken to court alongside the mobsters, suspected for murdering Skinner.
The show's tendency to play with expectations is rife here, taking perceived clichés within this mobster storyline and twisting them with glee. It also cements Principal Skinner and Chief Wiggum as a comedy powerhouses with their spotlighted roles. It's got a bunch of great jokes and lovingly provides a light send-up of mobster movies such as The Godfather series.
Flaming Moe's
(Season 3, Episode 10)
Moe Szyslak got his big break as a Simpsons character with this episode and what a great intro to his character it is. A rivalry tale between Moe and Homer, kept buyant with a lively party atmosphere, constant surprises and variety of cast in play.
Moe is struggling financially but things start going on the up for him and his tavern after Homer shows him a flashy drink he invented called the 'Flaming Homer'. Moe rebrands the drink the 'Flaming Moe' and it becomes a hit amongst the people of Springfield. It even attracts Aerosmith to make the tavern their hangout spot. Homer is hurt by Moe's betrayal and is jealous of his success, leading to him looking to get some revenge.
This is a pure fun episode and is lively from start to finish. It's cool to see how they develop Moe into a fully fledged cast member and Homer's typical stupidity leads to laughs. While cultural references to Cheers and a direct appearance from Aerosmith date this episode, the core plot is strong enough and so well paced that they're easy to overlook. Also having Aerosmith around for a musical number is smart for sure. It's a typically joke filled fun episode that has enough extra moments to float this one to the cream of the crop of early Simpsons episodes.
Radio Bart
(Season 3, Episode 14)
Radio Bart is one of the best scripted episodes of early Simpsons, going for a larger scaled plot than most episodes would attempt. It's an early example of a plot that involves Springfield as a whole and feels a like a refreshing change of pace in amongst the other season 1-3 episodes.
Homer buys Bart a microphone that transmits to nearby radios. Bart is initially disappointed with the gift, but finds crafty a use for it by lowering a radio down a well and transmitting his voice down there and pretending to be "Timmy", a boy who fell down the well. This prank is a runaway hit for Bart, as the entire town of Springfield falls for it and begins trying various unsuccessful efforts to save "Timmy". Even the media is lapping up the story and creating all sorts of sensationalist stories about the boy stuck in the well. However, Bart becomes worried he'll get in trouble for the prank when he remembers he labelled the radio with a nametag, so he tries to retrieve the radio from the well, but in a classic case of 'the boy who cried wolf' he gets stuck down there himself. Angry at Bart, the town of Springfield collectively decides not to rescue him, much to Bart's distress, but Homer is there to lead and charge and rescue his son.
It's pretty simple in terms of plot but layered with great satire and all sorts of really funny moments. We get a lot of incompetence from the people of Springfield and some strong satirisation of how seedy the entertainment industry can be, when Krusty brings in none other than Sting to make a hilarious charity single in support of "Timmy". A 'boy who cried wolf' twist feels inevitable, but is well displayed and sneaks in a surprise emotional punch as Bart has a speech about how much he'll miss out on is he's stuck in the well. It's a very well balanced episode and contains much of what you'd want an ideal Simpsons episode to contain.
Bart The Lover
(Season 3, Episode 16)
While there were a few gags that started to develop Mrs. Krabappel's character, this episode was the first time she's given a bit of a spotlight. Bart is in perpetual detention as usual and while unsupervised in Mrs. Krabappel's classroom he finds her personal ad in her desk drawer. Bart decides to prank her by responding to the ad, writing romantic letters under an alias.
This episode is strong due to the different perspectives presented. Bart's prank succeeding, but leading him to regret and to try and redeem himself is not a new idea for the show, but in putting a focus on Mrs. Krabappel's perspective it makes things captivating.
The collateral damage of the prank on Edna's lonely and frustrated day to day life is shown, meaning Bart's route to redemption is engaging as you want to see her get a win for once. Bart's scheme is nasty, but presented in a way that's forgiving and funny - like how he signs off his love letter with the fact his romantic alias hates yo-yo's, as Mrs. Krabappel had expressed to Bart's class earlier in the episode.
It makes for a really well rounded episode, even including a fun b-plot about Homer's quest to stop swearing so much under Flander's request. Often conflict developed out of a Simpson's childishness is not given the multi-dimensional approach as implemented here.
Bart's Friend Falls in Love
(Season 3, Episode 23)
Giving Milhouse some time in the spotlight is a nice change of pace for the show, but it's in the quality and quantity of jokes that this episode really becomes a highlight. While it's childhood romance plot is pretty barebones and predictable, The Simpsons makes a simple plot hugely engaging due to how sharp it is.
Milhouse falls in love with an exchange student named Samantha from Phoenix and this causes some strain on his friendship with Bart. As they start spending less time together, Bart's jealousy leads him to tipping off Samantha's strict father about her relationship with Milhouse, who sends her to an all girls catholic school.
It feels like an episode that features some of the smaller ideas for jokes that they possibly couldn't work into a big storyline. An opening vignette that parodies Raiders of the Lost Ark is great, it's funny without the need for dialogue. It's one of the best and most elaborately animated sequences of the show up until this point. Bart's class watch a satirical sex education video which leads to a series of rapid fire gags that all land.
There's a fun b-plot involving Homer's quest to lose weight as well, leading to some good laughs. It's the combination of a silly melodramatic romance with so many absurd jokes that really makes this episode special. Lots of little sequences in the plot, like Martin trying to entertain Bart by playing his lute, are just gold.