The Simpsonsis one of the most important television shows of all time, and became the most dominant property in mass entertainment culture for the first decade of its existence. While many would point to the cutting-edge animation, surprisingly nuanced social satire, and collection of instantly iconic characters as the reason that the series has managed to still be relevant in 2025,The Simpsonsstill continues to be an object of fascination because it is just that funny.
Few comedy shows have as many great episodes asThe Simpsons, as many fans would argue that the first ten seasons are among the best in the history of television. While listing all of the best episodes ofThe Simpsonscould be a seemingly never ending challenge, there are some standouts that significantly impacted the future of the show. Here are the ten funniestThe Simpsonsepisodes of all-time, ranked.
The Simpsons
10"Homer’s Enemy"
Season 8, Episode 23 (1997)
“Homer’s Enemy” managed to completely invert expectations of the show, as it explored what it would be like for another character to have to deal with all the chaos and confusion that Homer added to the world on a daily basis. AlthoughHank Azariahad played many iconic characters onThe Simpsons, he lent his voice to the role of Frank Grimes, a frustrated employee at the Springfield Nuclear Power Plant who gets increasingly frustrated by Homer’s erratic and unusual behavior.
“Homer’s Enemy” is one of thedarkest episodes ofThe Simpsons, and indicated that the show’s writers were aware of the reputation that its characters had earned after being on television for nearly a decade. The more focused, small-scale storyline actually was more hilarious than some of the more ambitious episodes could ever be, as it was exclusively centered on Grimes and his fall from grace.
9"Mayored to the Mob"
Season 10, Episode 9 (1998)
“Mayored to the Mob” was one of the last truly “great” episodes ofThe Simpsons, as most fans agree that the show began to experience a significant decline in quality after its eleventh season. However, “Mayored to the Mob” offered a fun satire of films likeMarried to the MobandMy Cousin Vinnyas it explored a conspiracy surrounding the corrupt Mayor Quimby.
“Mayored to the Mob” is best known for the cameo appearance byMark Hamill, who voiced a version of himself that is saved by Homer at a comic book convention, and subsequently hires him to become a bodyguard. Hamill is obviously well-versed in animation, having provided the voice for the Joker inBatman: The Animated Seriesand many other DC animated projects, and does a great job at making fun of himself in this hilarious episode.
8"Last Exit to Springfield"
Season 4, Episode 17 (1993)
“Last Exit to Springfield” is one of the most ambitious episodes ofThe Simpsons, as it forced Homer into the position of being a legitimate leader when he is tasked with leading the strike against the Springfield Nuclear Power Plant for its hazardous conditions and unfair wages.
While it’s a surprisingly nuanced satire of capitalism and the greed of corporations, “Last Exit to Springfield” was a great showcase for why Mr. Burns was such acompelling villain withinThe Simpsons' universe. The combination of blind arrogance, unchecked greed, and complete ignorance makes Burns a character that is too goofy to fully hate, as his acts of aggression often feel more comical than they are frightening. “Last Exit to Springfield” was able to show the strange working relationship between Homer and Burns, who, for better or worse, need each other to exist.
7"The Way We Was"
Season 2, Episode 12 (1991)
“The Way We Was” was the first flashback episodeofThe Simpsons, and introduced a younger version of Homer and Marge during the time in which they first fell in love with one another while still in high school. It’s very amusing to see the various references that are made to various coming-of-age and romantic comedy films, but it’s also funny to see how drastically different Homer and Marge looked and acted before they became parents.
“The Way We Was” is one of the sweetest and most sincere episodes ofThe Simpsons, as it offers an explanation as to why Homer and Marge still care about each other, despite the frequent fights that they have gotten into over the years. Nonetheless, seeing them have to survive the pressures of high school openedThe Simpsonsup to a different style of humor.
6"Flaming Moe’s"
Season 3, Episode 10 (1991)
“Flaming Moe’s” has one of the funniest premises of any episode ofThe Simpsons, as it focuses on a rivalry that emerges between Moe and Homer after they attempt to sell a mysterious alcoholic drink that somehow becomes increasingly popular in Springfield. Although the episode does have some slightly edgier jokes about alcoholism and other addiction issues, there’s also enough straightforward comedy about the ridiculous nature of the beverage that is being served.
“Flaming Moe’s” was a perfect way for the show to spotlight Moe, who has always been one of the most underrated and consistently funny characters onThe Simpsons. Even though Moe is a character who is met with constant bad luck and misery, he’s still someone who fans are willing to get invested in based on the possibility that he might eventually get a win in the end.
5"Deep Space Homer"
Season 5, Episode 15 (1994)
“Deep Space Homer” was one of thefirst episodes ofThe Simpsonsthat leaned into science fiction territory, as it involved Homer being selected to join the crew of a spacecraft. While there have been many great episodes throughout the history of the show in which Homer is selected for a mission or position that he is in no way qualified for, few of them are quite as funny as the idea that he would have to travel into space.
“Deep Space Homer” showed how expertly the show’s writers had managed to capture Homer’s personality, as while he is clueless to an absurd degree, he never acts like a jerk or does anything that would inadvertently cause harm to his family or friends back in Springfield. However, the surprisingly great visual gags indicated thatThe Simpsonshad radically improved its animation since the first season.
4"Cape Feare"
Season 5, Episode 2 (1993)
“Cape Feare” is one of the greatest parody episodes ofThe Simpsonsever, as it lampoons the premise ofMartin Scorsese’s 1991 remake of the classic thriller filmCape Fear, which had starredRobert De Niro,Nick Nolte, andJuliette Lewis. In “Cape Feare,” Sideshow Bob (Kelsey Grammarin a brilliant guest role) manages to escape from prison, and decides to finally track down and kill Bart for putting him behind bars.
“Cape Feare” manages to be surprisingly intense at times, as it shows how Bart’s fears materialize into his everyday life after he hears about Bob’s return. However,the greatest punchline is that Bob himself isn’t as competent as a serial killer as he claimed to be; seeing Bob get foiled once again by Bart set up a recurring rivalry that would continue to expand with subsequent seasons of the show.
3"Simpsons Roasting on an Open Fire"
Season 1, Episode 1 (1989)
The first episode ofThe Simpsonsis also one of the funniest, as it perfectly outlines what made each of the characters unique and gives a concise version of the episodic structure that would make the show so successful for nearly four decades. “Simpsons Roasting on an Open Fire” tells a veryrelatable story about Homertrying to give his family presents on the holiday, despite not having the resources to afford the gifts that he had intended to buy.
Homer’s bad luck inspires a lot of the main jokes in “Simpsons Roasting on an Open Fire,”but the episode still manages to end on a heartfelt note that shows why the Simpson family still cares for each other. The episode also provided the perfect origin story for how the Simpsons acquired their dog, whom Bart decides to name “Santa’s Littlest Helper.”
2"Mr. Plow"
Season 4, Episode 9 (1992)
“Mr. Plow” is the epitome of whatThe Simpsonscould do, as the episode takes a seemingly straightforward premise and escalates it to the point of complete absurdity. After Springfield becomes trapped within a disastrous snowstorm, Homer and Barney both start competing plowing businesses, and their rivalry grows more tenuous as the story moves on.
“Mr. Plow” showed how inventive, selfish, and empathetic Homer could be when he had his mind on something, as he often proves to be a far more complex character than he appears to be. Although it’s hilarious to see a different version of Barney, who actually takes an active role in doing something that he is good at, the best and funniest part of “Mr. Plow” is the hilarious jingle that Homer writes and performs to showcase his business; its one of the show’s best musical moments.
1"Marge vs. the Monorail"
Season 4, Episode 12 (1993)
“Marge vs. the Monorail” is a perfectly structured episodeofThe Simpsonsthat includes a great musical number, several hilarious visual gags, terrific guest stars, and great lines for every member of the Simpson family. In a parody ofThe Music Man, the charismatic salesman Lyle Lanley (Phil Hartman) travels to Springfield to propose that the city uses its extra funds to invest in an expensive, yet dangerous monorail train system; while Marge is concerned that the money would be better served if it went back to improving public works, the city overwhelmingly votes to build the train, and makes Homer one of its drivers.
“Marge vs. The Monorail” explores how disastrous Sprignfield can bewhen its citizens are left to make decisions on their own, and featured one of the best cameo appearances in the history of the entire show whenLeonard Nimoyappeared as a fictional version of himself.
