The Simpsons is one of the funniest shows ever created. While you can debate the show’s current quality level in 2023, it would be very hard to argue that the incredibly long-lived animated series doesn’t have a lengthy list of fantastic and hilarious episodes.
But which of these classic, beloved, oft-quoted, and funny episodes are the best of the best? Well, figuring that out will always be hard — there are just so many great episodes — but I did the hard work and settled on 20 episodes I consider the greatest of all time. Why 20? Because cutting more episodes seemed impossible, and it was easier to add stuff I love. That might explain how this started life as a top 10 and then grew…
Anyway, here are the 20 best episodes of The Simpsons in no particular order.
“Cape Feare” – Season 5, Episode 2
After Sideshow Bob is released from prison he comes after Bart, and the family is forced into witness protection. A parody of Cape Fear, this season five episode features iconic jokes and gags. I mean, this is the episode where Sideshow Bob keeps stepping on rakes. Plus “Die Bart, Die” and Homer failing to remember his new witness protection name are all in this episode, too. Classic stuff, and that’s not even mentioning the zany, perfect ending.
“Homer at the Bat” – Season 3, Episode 17
Mr. Burns makes a big bet that his nuclear power plant’s softball team, led by Homer, can beat another rich guy’s team. And to help win, Burns hires ringers in the form of nine MLB pros. What follows is a wild and wacky episode. While this wasn’t the show’s first time including celebrity cameos, at the time it was the most it had done in one outing. This episode is also historic, as it was the first time The Simpsons beat The Cosby Show in ratings.
“Marge vs. the Monorail” – Season 4, Episode 12
It’s funny to remember that, back when this episode aired in 1993, it caused some controversy among fans and viewers over its less grounded, more over-the-top plotline and jokes. And yeah, “Marge vs. the Monorail” is very weird compared to what had come in the previous four seasons. I mean, Star Trek’s Leonard Nimoy literally teleports away. But who cares! This Conan O’Brien-penned episode features the Monorail song and a lot of Phil Hartman as the singing con artist, Lyle Lanely. How can you hate that?
“Bart After Dark” – Season 8, Episode 5
Y’know that gif where Grandpa Simpson walks into the room, sees Bart, and then walks back out in one smooth move? That’s from this episode. And it’s just one of the many great jokes tucked neatly inside this classic that sees Bart working part-time at a secret brothel as Homer tries (and fails) to take care of him while Marge and Lisa are off cleaning rocks after a nasty oil spill. But hey, you just want to hear the big song from the ending, so here you go.
“Homer the Great” – Season 6, Ep 12
Home joins a secret and all-powerful group, screws up, but then becomes its all-powerful leader. That’s basically a perfect formula for a silly episode of The Simpsons. Even better, “Homer the Great” features a wonderful performance from Patrick Stewart and includes another classic song, the Emmy-nominated “We Do.” Oh, and the near-perfect “stone of shame and triumph” joke, too.
“Two Cars in Every Garage and Three Eyes on Every Fish” – Season 2, Episode 4
In this classic from season two, Mr. Burns decides to run for governor in order to keep his nuclear power plant safe from a government shutdown. And while this episode’s political satire and jokes are great — not to mention the introduction of the show’s iconic three-eyed fish, Blinky — what really helps land this episode among the best ever is surprise ending, in which Marge is able to screw Burns’ entire campaign over with a simple meal.
“22 Short Films About Springfield” – Season 7, Episode 21
Steamed Hams. That’s about all I need to say and I think most people will agree this episode deserves a spot here. Yes, that classic segment originated here in this episode that changes up the usual Simpsons formula and includes tiny vignettes featuring other characters. Sure, Steamed Hams gets all the glory today, but let’s not forget other quality bits, including Dr. Frink’s panicked attempt to tell his story at the end and the “very tall man in a small car” segment with Springfield’s famous bully, Nelson. “Let’s laugh at him!”
“Treehouse of Horror VI” – Season 7, Episode 6
Picking just one Treehouse of Horror episode was tricky. But ultimately this season seven instalment in the animated show’s long-running Halloween tradition just barely beat out the other entries thanks to its innovative and memorable 3D CG Homer segment, the fantastic Nightmare on Elm Street parody featuring Willie, and the story in which Paul Anaka sings away the giant evil monsters. Remember: Just don’t look! Just don’t look!
“Two Dozen and One Greyhounds” – Season 6, Episode 20
I’m noticing a trend with my picks. The episodes that feature big, silly songs are showing up more often. But even without the excellent “See My Vest” number, this 101 Dalmations-inspired episode from season six would still make the cut. It’s got so many classic jokes including one of the all-time greats, with Homer eating a stack of cheese slices while Burns and Smithers try to break in to steal all of the Simpsons’ little puppies.
“Lisa’s Substitute” – Season 2, Episode 19
Legally, anyone creating a best-of Simpsons ranking has to include “Lisa’s Substitute.” And for a good reason: It’s a perfect episode about Lisa meeting a joyful and supportive substitute teacher who leaves shortly afterward, destroying her in the process. It’s an example of how the show isn’t just great at jokes, but also at telling heartwarming stories. (And let’s ignore the shitty joke in season 25 where he briefly returns but Lisa is too busy to see him. Fuck I hate that joke so much.)
“Halloween of Horror”- Season 27, Episode 4
Praising newer episodes like this one is always risky as someone will jump into the comments to suggest we screwed up and wasted space on a “crappy, modern episode.” Thing is, “Halloween of Horror” is genuinely fantastic. It’s the first (and so far only) time the show has done a down-to-Earth, non-Treehouse of Horror halloween episode, letting the writers finally make jokes about adults dressing up as sexy characters and all the pop-up shops that appear during October.
The episode’s story — revolving around Lisa becoming scared of Halloween and Homer having to teach her how to handle fear during a home invasion — also stands toe to toe with any classic Simpsons half-hour. If you haven’t watched an episode since season 12 or so, I’d highly recommend “Halloween of Horror,” especially if you love the spooky season.
“And Maggie Makes Three” – Season 6, Episode 13
Flashback episodes can be tricky to pull off in a show that’s been on for as long as The Simpsons. (Recent flashback episodes suggest Homer was a teen in the ‘90s, which makes no sense but whatever…) However, “And Maggie Makes Three” from season six avoids this pitfall by basically not focusing on the era and instead using the flashback to tell us how Maggie came to be. For anyone who has worked a job they hate because it paid well, this episode will hit hard. And that ending still makes me tear up a bit.
“Mr. Plow” – Season 4, Episode 9
OK, everyone, sing it with me: “Call Mr. Plow, that’s my name, that name again is Mr. Plow.” Sure, the song and snow plow rivalry between Homer and Barney is the real meat of this episode. But I think it often means people forget about the incredible Adam West cameo in this classic. It should be noted that this was before his stint on Family Guy and his resurgence as an odd but loveable goof who used to play Batman. “And how come Batman doesn’t dance anymore?”
“The City of New York vs. Homer Simpson” – Season 9, Episode 1
Any time the show really cranks up Homer’s frustration and anger is a win, and in this season nine episode, Homer gets so fed up and angry about his car getting stuck in NYC that he ends up leaving the city with the boot still on the tire, leading to one of the best endings in the show’s entire run. But let’s not forget that while Homer is stuck in his car, the rest of the family is out running into an endless parade of funny New York parody jokes.
“Last Exit to Springfield” – Season 4, Episode 17
When Lisa needs braces, Homer steps up to make sure the power plant’s union doesn’t let Burns revoke dental coverage. And thanks to being stupid and lucky, he’s able to convince Burns that he’s a smart negotiator and eventually leads a successful strike in a fantastic episode that features some truly classic jokes. Oh, and Lisa plays Classical Gas while Lenny jams out. It’s the kind of joke that wouldn’t happen today in the show, but back in the early, slower seasons, it fits perfectly and is still fondly remembered to this day.
“You Only Move Twice” – Season 8, Episode 2
Homer becoming an employee of a maniacal Bond villain is already a golden idea. But then the show cast Albert Brooks as its main villain, Hank Scorpio, and in the process created one of the best 30 minutes of TV ever aired. I still reference this episode any time I throw my shoes into the corner of the room or when I hear someone mention the word hammock. You could argue that Lisa doesn’t get much to do here, but the rest of it is so strong and funny that I’m not sure it matters.
“Bart the Daredevil” – Season 2, Episode 8
This episode contains what might be the most well-known, iconic scene from the entire franchise: Homer jumping the Springfield Gorge and failing. It’s a scene the show’s writers have endlessly referenced, including with a direct nod in The Simpsons Movie. But don’t assume “Bart the Daredevil” is a one-trick pony. The episode features some other classic jokes, like the hospital ward filled with kids who did dumb stunts. It’s also the first appearance of Dr. Hibbert.
“Mother Simpson” – Season 7, Episode 8
What makes for a good episode of The Simpsons? I think it needs to include some wonderful jokes, for sure. In fact, great jokes can often overcome other shortcomings. But if an episode also features some heart and genuine emotion, it becomes something special.
That’s the case with “Mother Simpson,” one of the show’s best episodes. After faking his own death, Homer discovers his mother (voiced by Glenn Close) did the same, and learns why she left him as a kid. And when she has to leave again and Homer is left sitting on the hood of his car, alone, staring at the stars, it’s an oddly poignant and touching moment from a show that has featured countless wacky shenanigans over the years.
“Deep Space Homer” – Season 5, Episode 15
And now, for the exact opposite of touching. “Deep Space Homer” is a ridiculous joke machine that features Homer Simpson going into space. It’s pure nonsense, but extremely funny nonsense. The bit where Homer eats the spinning potato chip is both artful, impressive, and hilarious. And if you ever wondered where that Kent Brockman meme about insect overlords came from, here’s the source.
“Holidays of Future Passed” – Season 23, Episode 9
One day, The Simpsons will end. Seems hard to believe, but it will happen. And I’ll be excited to see how the writers and showrunners finally end this massive series. But I’ll also be sad that back in season 23 they burned what would have been a great finale so early. Since “Holidays of Future Passed,” the show has popped into the future multiple times to give us additional aged-up Bart and Lisa material. Yet this is still the best example of the series showing us a glimpse of the future.
Seeing Bart and Lisa struggling to be parents is both sad and also believable. With a dad like Homer and a family life filled with all the wild stuff they saw for so many years, it’s not shocking the two of them are struggling as parents. But it’s not a downer episode either, actually ending on a positive note. And like the very first episode of the series way back in 1989, the whole thing happens during Christmas. I’m still excited to see what the actual finale ends up being one day, but I’ll probably remain a bit bummed that it wasn’t “Holidays of Future Passed.”
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