The Simpsons: 10 funniest episodes of all time

The Simpsons arrived in 1989 and redefined prime-time entertainment with what it had to offer: a sitcom that focused on a working-class family while also delivering scathingly dark humor with each new episode.

It was a show that never shied away from weaving in biting satires and swift pop culture riffs. It reimagined the boundaries of a medium like animation. The Simpsons turned Springfield into a living, breathing space where each gag was layered and had subtextual richness.

The visuals were clever, and the jokes were well written, making the show one of the most lasting pop cultural icons of modern times. The show is also famous for its weirdly accurate prophecies, making it resurface in pop cultural discussions again and again.

While the show is popular in its own right, it arguably had a golden era. Episodes that came out during that time were mostly successful in striking a good blend between sharp social commentary and character-driven stories.

So, here are ten episodes that still hold up in their comic appeal decades later.

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The Simpsons: 10 funniest episodes of all time

10. "And Maggie Makes Three" (Season 6, Episode 13)

In this episode, Marge ponders back on Maggie’s birth and Homer quitting the power plant for his dream job at a bowling alley. The humor lies in situational hooks and sharp ironies. Homer is blissfully ignorant of Marge’s pregnancy.

On top of it, he is weirdly oblivious to any baby-related compliments. The episode relies on self-sabotage humor when Homer is seen shrinking through a tiny door to beg for his job back. This blends comedy and heart, making it one of the most standout Simpson episodes.

9. "Homer's Enemy" (Season 8, Episode 23)

In Episode 23 of Season 8, Frank Grimes is introduced as a hardworking worker infuriated by Homer’s incompetence and undeserved success at Springfield Nuclear Power. This episode's chaos focuses heavily on dark satire breaking off its own reality.

Grimes becomes the audience’s voice of reason, inducing a smart meta-humor. He wants the viewers to feel the frustration escalating until his absurd, fatal meltdown.

Homer, however, stays blissfully unaware as usual, making this a biting, self-aware critique of the show’s own universe.

8. "Marge vs. the Monorail" (Season 4, Episode 12)

Here, civic satire and musical comedy run simultaneously. When a clever con man sells Springfield a faulty monorail, it leads to the popular “Monorail Song.”

As the conductor, Homer must check the runaway train as Marge gets to the root of the scam. The episode also brought in a guest star, Leonard Nimoy.

7. "Mayored to the Mob" (Season 10, Episode 9)

What made this episode hilarious is how it wove in a mob movie genre parody, presenting Homer as Mayor Quimby’s bodyguard.

The highlight and fan favorite moment comes when Mark Hamill plays himself at a sci-fi convention, giving a nudge to his Star Wars popularity. The self-deprecating humor is unmistakably a classic Simpsons feature.

Sharp writing and confident pacing retain audience attention with ambitious homages without cutting on the Springfield absurdity.

6. "Cape Feare" (Season 5, Episode 2)

This Simpsons episode makes a loving parody of the film Cape Fear. Here, the comedic hit and the scathing slapstick get subtly heightened. Sideshow Bob, voiced by the brilliant Kelsey Grammer, is paroled and, upon coming out, starts to send Bart death threats.

Physical gags are just as good, mainly aimed at Bob, including his chaotic scene of stepping on multiple rakes.

What makes this episode brilliant is its ability to subvert the tension of a typical thriller. It uses a villain who is scary but comically incompetent.

5. "Radioactive Man" (Season 7, Episode 2)

Episode 2 from the show’s 7th season masterfully spoofs Hollywood and the superhero genre. It all unfolds when a reputed production house sets the shooting location at Springfield for a big-budget Radioactive Man movie.

The lead actor of the film is Rainier Wolfcastle, and the comedy is rooted in the irony of expectation vs. reality. Bart wants to play Fallout Boy, but his hopes are dashed when the role goes to a reluctant Milhouse.

The episode offers a satirical commentary on showbiz as the town's greedy officials bleed the studio dry with bogus taxes and fees.

4. "The Way We Was" (Season 2, Episode 12)

This emotional story for Homer and Marge’s budding relationship was served with 1970s pop culture nods and teenage awkwardness.

What makes this episode relatable is Homer’s bumbling charm and the novelty of seeing the characters as younger versions of themselves. In this episode, The Simpsons strikes another impressive balance of sweet nostalgia and sharp gags.

3. "22 Short Films About Springfield" (Season 7, Episode 21)

This masterclass episode is built upon the iconic cult film by Tarantino called Pulp Fiction. Here, the show delivers rapid-fire vignettes about Springfield’s residents, while the comedy relies on micro-gags and self-referential wit.

Who can forget the infamous “Steamed Hams” gag, where Principal Skinner chaotically covers up a burnt dinner? It just solidifies The Simpsons' mastery over characters and how they can steal the show in seconds.

2. "You Only Move Twice" (Season 8, Episode 2)

In a rare turn of events, the Simpson family is spotted outside the usual setting. They relocate to a seemingly calm town where Homer starts his job for the affable Hank Scorpio.

The man in question is found to be a Bond-style supervillain. The humor stems again from Homer’s obliviousness. He does not pay much heed to Scorpio’s villainy, contrasting with his family’s misery.

The final punchline, when Homer gets the Denver Broncos as a gift, is a masterclass in top-tier absurdism.

1. "Last Exit to Springfield" (Season 4, Episode 17)

The 17th episode from The Simpsons’ 4th season earns a top-spot mention because of its brilliant mix of absurd hilarity and narrative tightness. Homer, now a union leader, fights to keep the dental plan so Lisa can get her brace done.

He is trying to outwit (unintentionally) Mr. Burns at every turn. The “Lisa needs braces” chant showcases how the episode was able to turn even the smallest, simplest repetition into immortal comedy.

Further, fans loved it for its crisp yet subtle political satire, character humor, and emotional beats played in delicious proportions.