10 Most Rewatchable Simpsons Episodes That Never Get Old

Although the Golden Age of The Simpsons ended decades ago, fans still rewatch their favorite episodes over and over again. While everyone has their own personal favorites, some episodes are simply better-suited to multiple rewatches. They never lose their appeal, and they can even become more enjoyable after a few watches. These episodes usually highlight something that the show does incredibly well.

The Simpsons is one of the best shows to rewatch, because the comedy is so fast-paced and chaotic. An episode can bounce around between witty dialogue, ludicrous slapstick, and wry parody. Sometimes the show can even throw in a moment of heartbreaking drama. Although it observes pop culture, stereotypes and human foibles, The Simpsons also delves into the depths of human emotion, and this gives the show several hidden layers.

10 “Mother Simpson”

Season 7, Episode 8.

The Simpsons isn’t afraid to get emotional at times, but the real brilliance of the show is that it can deliver heartbreaking episodes while still remaining as hilarious as ever. In “Mother Simpson,” Homer is reunited with his mother, who left when he was just a child. He’s so happy to see her again that he turns into a giddy child, showing off in front of her and trying to make up for lost time.

Mona’s short time in Springfield gives Lisa a new kind of female role model, and the flashback scenes are just as enjoyable. Mona’s free spirit is contrasted beautifully with Grampa Simpson’s curmudgeonly old-man routine. Ultimately, Homer’s glee is short-lived, as Mona has to continue her life on the run. The episode ends with one of the most poignant images in the show’s history, as Homer looks up at a starry sky, saying goodbye to his childhood once and for all.

9 “$pringfield (Or, How I Learned To Stop Worrying & Love Legalized Gambling)”

Season 5, Episode 10.

When Springfield legalizes gambling to bring in some extra revenue, Mr. Burns sets up a casino to tighten his financial grip on the town. Although there are a lot of fun scenes in the casino, the episode’s greatest strength is how it shows the Simpson family struggling to cope without Marge. Homer, for all the love in his heart, is a woefully inept parent, and it doesn’t take long for the house to fall into disrepair.

The episode’s title is a play on Dr. Strangelove, but “$pringfield” takes inspiration from another Stanley Kubrick film, as Mr. Burns loses all touch with reality in a sanitized bedroom reminiscent of the ending of 2001: A Space Odyssey. The moment that he tries to force Smithers into the Spruce Moose is just one of countless great jokes in “$pringfield” that make the episode so enjoyable to rewatch. Bart’s treehouse casino is also the source of many a fine gag, including guest star Robert Goulet’s unforgettable line read: “Vera said that?”

8 “You Only Move Twice”

Season 8, Episode 2.

The Simpsons has produced plenty of great characters who only appear in a single episode, including straight-talking Elliot Ness-type Rex Banner and slimy monorail huckster Lyle Lanley, but Hank Scorpio has them all beat. The megalomaniac businessman is ripped straight from a Bond movie, and “You Only Move Twice” is an inspired Bond parody that sees things from a different perspective.

Every one of Hank Scorpio’s lines is gold, and it’s worth rewatching “You Only Move Twice” just to luxuriate in his presence for as long as possible. The deranged villain with pockets full of loose sugar steals the spotlight, but the episode also devotes enough time to the Simpson family in their new surroundings. Homer is the only one who benefits from the change of scenery, but he decides to give up his dream job for his family, and he only gets the Denver Broncos as a consolation prize.

7 “Homer At The Bat”

Season 3, Episode 16.

The Simpsons has a long-standing tradition of great guest stars playing themselves. The show has hosted Stephen Hawking, Thomas Pynchon, and three Beatles, and “Homer at the Bat” includes a total of nine MLB stars. When Mr. Burns makes a bet on his company’s upcoming softball game against a rival’s nuclear power plant, he stacks the roster with players including Wade Boggs and Jose Canseco.

“Homer at the Bat” perfects the special Simpsons formula for guest stars. The baseball players aren’t just there to boost the show’s publicity, they fully buy in to the cartoonish misadventures. It’s testament to the episode’s enduring appeal that international fans with no concept of Don Mattingley can still find it just as funny when Mr. Burns keeps telling him to shave his sideburns.

6 “22 Short Films About Springfield”

Season 7, Episode 21.

“22 Short Films About Springfield” weaves an interconnected narrative across the entire town that gives some of The Simpsons’ best minor characters a chance to shine. Each segment is like a miniature episode, but the Simpson family fade into the background. Lisa gets gum in her hair and Homer accidentally traps Maggie in a newspaper vending box, and this is pretty much the extent of their involvement.

The Simpsons has mined a lot of comedy out of the zany inhabitants of Springfield, and this episode gives the writers the freedom to concoct bizarre situations that have nothing to do with the Simpson family. Principal Skinner and Superintendent Chalmers’ “steamed hams” luncheon is a perfect sketch. Bumblebee Man’s slapstick and fiasco and Chief Wiggum’s Pulp Fiction parody are two other highlights. The only character who doesn’t get his time in the sun is Professor Frink.

5 “Bart The Murderer”

Season 3, Episode 4.

While The Simpsons is known for its movie parodies, some of the jokes can be lost on fans who aren’t familiar with the source material. Watching a lot of Stanley Kubrick and Alfred Hitchcock will give fans a handy key to understanding plenty of the show’s references. “Bart the Murderer” works so well because it is a broader genre parody. Fat Tony and his associates take inspiration from The Godfather, Martin Scorsese’s movies, and old film noir gangsters, but there isn’t one specific reference that the viewer needs to grasp.

The Simpsons is often a show that chews up and regurgitates pop culture in interesting ways. “Bart the Murderer” has many of the hallmarks of classic gangster movies, but it’s surprisingly original and compelling. The emotional core of the story is about Bart’s hubris, and the way he learns his lesson. The hilarious gangster parody and the farcical court case are just the icing on the cake.

4 “The Itchy & Scratchy & Poochie Show”

Season 8, Episode 14.

The Simpsons often uses Krusty the Clown’s Itchy & Scratchy Show to comment on itself and its fans. This self-parody reaches its peak in the season 8 episode “The Itchy & Scratchy & Poochie Show,” in which the cartoon is forced to find a way to stay fresh after their ratings take a nosedive. This episode shows the writers of The Simpsons predicting the show’s downfall, and questioning how long they can keep the good times rolling.

“The Itchy & Scratchy & Poochie Show” is a great episode without any of this context. It can still be seen as a satire of TV shows that don’t know when the party is over and try desperately to maintain relevance. However, given that it aired toward the end of the Golden Age of The Simpsons, the episode has taken on a meta position as the harbinger of the show’s decline. The worst seasons of The Simpsons are filled with Poochies, whether they come in the form of boring guest stars, tired old tropes, or unpopular new characters.

3 “Treehouse Of Horror V”

Season 6, Episode 6.

The Simpsons’ Treehouse of Horror episodes are the show’s greatest tradition. Each season brings a new anthology episode of three or four spooky tales for Halloween, usually referencing popular horror or sci-fi stories. “Treehouse of Horror V” is arguably the best of the bunch, and it can be rewatched every October without losing any of its charm. Although this could also be said for a few other Treehouse of Horror episodes.

“Treehouse of Horror V” starts off with a brilliantly observed parody of The Shining, as Homer becomes the caretaker at one of Mr. Burns’ sprawling mansions during a violent snowstorm. This is the most eye-catching segment, but the next two are just as funny. Homer’s misadventures with time travel are inspired by a Ray Bradbury story, but they apply to any time travel movie or TV show. The final segment, “Nightmare Cafeteria”, is as scary as it is funny.

2 “Marge Be Not Proud”

Season 7, Episode 11.

As well as the Treehouse of Horror episodes, The Simpsons can always be relied upon to produce a heartwarming Christmas episode. The show’s very first episode is a Christmas story about how the family got their faithful dog, Santa’s Little Helper, and most seasons since then have kept the tradition alive. “Marge Be Not Proud” is a popular festive delight for fans of the show, who can return to it each year just like any classic holiday movie.

To make room for its touching ending, “Marge Be Not Proud” goes to some very dark places. After Bart is caught shoplifting the latest video game, Marge is at a complete loss. Bart fears a ferocious telling off, but he gets something much worse, as Marge gives up on him and retreats into self-reflection. Bart realizes that disappointing his mother is worse than any punishment she could dish out. He makes amends with a genuine display of humility and selflessness in the warm and fuzzy finale of The Simpsons‘ best Christmas episode.

1 Who Shot Mr. Burns?

Season 6, Episode 25 & Season 7, Episode 1.

The fantastic two-parter, “Who Shot Mr. Burns” paints a portrait of Springfield’s most diabolical villain, all while spinning a genuinely captivating mystery plot. Mr. Burns is one of the show’s greatest creations, and the cold-hearted business tycoon gets the most attention out of anyone who doesn’t have the surname Simpson. “Who Shot Mr. Burns” ratchets his villainy up to new heights, as he plans to block out the sun and plunge the town into eternal darkness.

There is no shortage of candidates for Mr. Burns’ would-be killer, and the investigation allows the show to dip in and out of different characters’ lives. The Simpsons’ “Who Shot Mr. Burns” mystery eventually comes to a satisfying conclusion that urges fans to go back and watch it all over again from the start, but the real joy of the two-part episode is that Springfield’s characters are pushed to their limits.