If you’re anything like me, one of the biggest draws of Disney+ was the inclusion of The Simpson’s. Sure, it’s been bad much longer than it’s been good now (it probably hasn’t been great since the start of the millennium), but don’t underestimate just how good it was in its prime.
It was probably the best thing on television in its first eight seasons. Those seasons still stand out as some of the greatest TV, animated or otherwise, of all time. The secret to its success was not just its astounding gags-per-minute ratio but its depth, its interwoven world, and surprising brevity. It also helps that these early episodes we so incredibly memorable and quotable. Even now, the uses of classic Simpson’s have been immortalised by countless GIFs (I’d say there’s a Simpson’s GIF for every occasion).
Think of this like my Christmas films playlist from last year; a good nudge in the direction of some top-quality stuff. Only this time about the longest-running TV series in history. Although it has now run into its 32nd (I think?) season and has just been renewed, I’ll be focusing exclusively on the first eight seasons of the show; the time most widely accepted as the show’s peak. This isn’t a comprehensive list of ALL the great Simpsons episodes; I’d be here all day. It’s merely a list of episodes I recommend as a starting point.
So with this in mind, I’ve been watching classic episodes of the show recently. Mostly to reassess whether I was looking back through rose-tinted goggles or whether the show actually was just that good. I’m happy to report that, for the most part, at least, the latter is true. Now I’m going to compile for you a list of my most recommended episodes to guide your own revisit to old Springfield. Enjoy.
Season 2, Episode 1 – Bart Gets an ‘F’
Although there are a few significant episodes in the show’s first season (with honourable mentions to ‘Moaning Lisa’ and ‘Krusty Gets Busted’), it only really began to find its feet in Season 2, and it really came out swinging.
This is an excellent example of what this show could do when it mixed an emotional heart with the stellar comedy. Up until this point, Bart has never shown any interest in school. He is usually more of an irritation to his teachers. However, this episode packs an almighty punch by having Bart try his best yet still seemingly come up short.
It must have been a great surprise to many watching at the time, as they realised that this silly little show about a yellow family could actually have an emotional impact, and not just emotional impact, but elicit a genuine feeling of empathy towards Bart. We have all, at some point in our lives, tried our best and failed. It’s a recognisable real-world feeling. The fact that this show could play off that, and play with our emotions in such a way, just gave us a glimpse into the genius writing the series had at its peak.
Season Two, Episode Eight – Bart the Daredevil
Another entry, another Bart episode. They really were pushing the troublemaker hard as the face of the series in the earlier days, weren’t they?
Some Simpsons episodes were great because of the depth of content; these episodes will have intricate ‘A’ stories, accompanied by an intriguing ‘B’ or even ‘C’ plot. They’ll be teeming with content and have the feeling of trying to fit all the best ideas into a small space. I’m sure we’ll come across a few of these as we go along. However, some other episodes are concentrated on one plot or idea. They wring every inch of potential out of a sometimes restrictive subject.
This episode sits in the latter category. It’s mainly remembered for its final third, but oh, what a final third. One of the most iconic scenes and pay-offs, one so ingrained in the show’s history, it was even alluded to in The Simpsons Movie nearly twenty years later.
It may be predominantly remembered for that ‘Springfield Gorge’ scene, but it is packed with gags and paid off with that iconic moment. It’s a very nostalgic watch for an old Springfield fan.
Season Three, Episode Nine – Flaming Moe’s
The series has created many enduring moments over the years; these legacies of nostalgia can form around anything, memorable scenes, characters, quotes, or, in this case, songs. It isn’t the most memorable tune from this show, it’s not even the most memorable from this season (wink, wink), but it’s still a memorable one that sticks in my mind. It’s a tune that instantly pops into my head just by looking at the title.
It’s also an episode that (obviously) highlights Moe, who can be hit-and-miss in terms of punchlines. I’m not so keen on the recurring gag of him being suicidal, as that’s a bit too close to the bone and perhaps a bit too dark for the show, but he has his moments too. His, shall we say, ‘questionable’ business practices and hair-trigger temper have elicited many a chuckle over the years, and he gets to have an episode more or less to himself here.
This episode doesn’t always show up on other Simpsons-related lists. It isn’t the strongest writing of the series or even the funniest. Still, it’s one that always sticks in my mind as being a little under-appreciated. Maybe it needs a revisit?
Season Three, Episode Sixteen – Homer at Bat
We’re talking softball, from Maine to San Diego, talking softball…
The best Simpsons song? Maybe. It’s a tough contest, but it’s in the race.
Yes, this is the memorable song I not-so-subtly referenced earlier. I don’t think that it’s the only string to the episodes bow, though, God no, there’s hilarious comedy, with laughs so good that it even makes shameless celebrity cameos into punchlines, taking aim at the celebrities themselves. A trope well-established within the series now but almost unheard of at the time.
The celebrity involvement (a group of baseball players, all of whom are strangers to this tea-slurping Brit) don’t even draw focus from the leading group of characters. Specifically, Homer, who finds himself as Mr Burns’ last hope for winning a softball (like baseball, but with a bigger ball, for those who aren’t from the States) competition. Because of a surreal string of events (from grotesquely-swollen jaws to run-ins with the law) , the actual sportsmen are out of action and Homer is the last batsman remaining. Combined with Mr Burns’ absurd coaching, it makes for a hilarious watch.
A real classic. One rightly considered to be one of the shows best.
Season 4, Episode 2 – A Streetcar Named Marge
This episode appeals to me, especially given my history in amateur dramatics. The sequences of rehearsals, especially of the director, hit a little close to home.
This episode also focuses n the relationship between Marge and Homer. Unlike many in many other episodes, Homer actually learns something, which is more than he’s done in any modern episode I’ve seen.
Episodes about Marge can be a mixed bag, as she isn’t the most exciting family member. I think a lot of that has to do with the lack of female writing staff back then, so Marge doesn’t have a lot of agency outside of being a wife and mother, but she gets to spread her wings here and stand out at last.
There’s a lot to like in this episode, basically. The content about Homer and Marge’s marriage, the distinctly untalented performers from Springfield, provide a lot of chuckles. There’s a memorable one-off character in the form of Jon Lovitz’s Llewellyn Sinclair, the, shall we say, “passionate” director of the production. Everything that makes up the classic formula.
Season 4, Episode 12 – Marge vs The Monorail
Season Four has a lot of solid-gold classics within its 22-episode run. It was difficult narrowing down this list for each season, let alone for the whole list, and season 4 was perhaps the hardest one of all to narrow down. Many episodes could have featured here, from ‘Kamp Krusty’ to ‘Krusty Got Kancelled’ (an excellent season to be a clown) as well as ‘Mr Plow’ and a few others. Still, I went for this one because it just has everything you want from a Simpson’s episode.
Firstly, there’s the memorable song, something I’ve discussed before, coupled with the one-off character who delivers it, Lyle Lanley, voiced by the late, great Phil Hartman. Who delivers another all-time great performance here as the con artist who sells the city the obviously faulty monorail. The Simpson’s has had a fair few memorable one-off characters, people who turn up for an episode and forever impress themselves on the audiences. Lyle Lanley might just be the best of the bunch, and a lot of that is down to Hartman’s lively performance.
Everything you can wish for in an episode of this show, the jokes’ hit-rate is astoundingly high. It makes excellent use of its celebrity guest star (Leonard Nimoy in a self-skewering appearance). Still, it retains a remarkable legacy, one of the episodes that frequently comes up in the conversation about the best in the show’s history.
Season 5, Episode 2 – Cape Feare
Sideshow Bob is rightly regarded as one of the show’s best recurring characters. In the glory days, his appearances were always something special. Always thinking of ways to get his revenge on Bart, he always manages to find a way out of prison and back into the family’s life.
‘Cape Feare’ is the pick of the litter when it comes to Sideshow Bob episodes. It’s one of the most creative episodes in terms of jokes the series has ever seen, and the result is a string of simply iconic gags. This is the episode that injected new life into jokes about rakes, after all.
Then, to wrap it all up is the most ridiculously brilliant finale, when, in a bid to buy time, Bart appeals to Bob’s ego and gets him to perform the score of HMS Pinafore. Climaxing in a very rousing rendition of ‘He Is an Englishman’ reaching a peak of both hilarity and tension, as we hope the boat arrives back in Springfield before the final note.
Another entry, another all-time great, not much else I can say, really.
Season 6, Episode 12 – Homer the Great
There was a time when The Simpson’s was also a sharp satire, rather than being a sterile timeslot-filler. In the sixth series, it decided to turn its eye to the Freemasons and other such fraternal organisations.
Another episode that includes a memorable earworm (something I think that says a lot about me, more than anything) in the form of ‘We Do’. Which sees the Stonecutters list off all the things they influence perfectly toes the line between hilarious and catchy in the way that all these songs seem to.
It also has a celebrity guest appearance, which I didn’t realise until I rewatched recently and checked the episodes IMDb page to find out that the voice of ‘Number One’ is none other than Patrick Stewart! It goes to show how unobtrusive their celebrity casting once was that I didn’t know this until now.
Another aspect in the episode’s favour is the many, many periphery characters; who now get their chance to be part of something more substantial than just hanging around in Springfield’s background. As it seems like all the male citizens of Springfield are members of the Stonecutters.
An episode that really makes the most of its concept, with the help of another catchy tune, it does enough to ensure its place on this list.
That brings my list at large to a close after only six seasons, but this is really only a tiny sample of the show’s best era. There are so many great episodes from those initial eight seasons that to write about them all would take several weeks. This list wasn’t intended to list the greatest or best episodes. They are merely a collection of episodes I would recommend to introduce yourself to the show or showing a non-fan friend to convert them. In the interest of completionism, here is a list of episodes that could have made it, if not for time and space allocation:
Simpsons Roasting on An Open Fire (Season 1, Episode 1)
Moaning Lisa (Season 1, Episode 6)
Krusty Gets Busted (Season 1, Episode 12)
The First Seven Treehouse of Horrors
Oh Brother, Where Art Thou? (Season 2, Episode 15)
Kamp Krusty (Season 4, Episode 1)
Mr. Plow (Season 4, Episode 9)
I Love Lisa (Season 4, Episode 15)
Last Exit to Springfield (Season 4, Episode 17)
Krusty Gets Kancelled (Season 4, Episode 22)
Homer’s Barbershop Quartet (Season 5, Episode 1)
Deep Space Homer (Season 5, Episode 15)
Sweet Seymour Skinner’s Badasssss Song (Season 5, Episode 19)
Bart of Darkness (Season 6, Episode 1)
Who Shot Mr Burns? Parts 1 & 2 (Season 6, Episode 25 & Season 7, Episode 1)
Radioactive Man (Season 7, Episode 2)
You Only Move Twice (Season 8, Episode 2)
Burns, Baby Burns (Season 8, Episode 4)
The Springfield Files (Season 8, Episode 10)
Homer’s Phobia (Season 8, Episode 15)