The Simpsons isn’t just a successful animated sitcom; it’s an American institution. With over 700 episodes since its 1989 inception, The Simpsons is the longest-running animated series, American sitcom, and scripted primetime TV series.
America’s favorite dysfunctional family, Homer, Marge, Bart, Lisa, and little Maggie, have more than 30 years’ worth of hijinks in the bag. While every fan has their favorite episode, most agree that these top 50 Simpsons episodes have the perfect mix of satire and irreverence that makes The Simpsons magical. With 36 seasons, it continues to prove it’s the longest-running American animated series. The best Simpsons episodes on IMDb continue to slightly shift with each new season, but still largely feature titles from the beloved classic Simpsons era.
50. “Homer’s Barbershop Quartet” (Season 5, Episode 1)
IMDb Rating: 8.5/10
The Simpsons Season 5 begins with a very good (though inaccurate) chalkboard gag: “I will never win an Emmy.” As it’s made repeatedly clear, “Homer’s Barbershop Quartet” is an extended parody of The Beatles’ rise to fame. It even has the legendary George Harrison as a guest star, making him the second Beatle to appear on The Simpsons (after Ringo). The fact that Homer has a good singing voice is hard to believe, but this episode is something we’re willing to suspend disbelief for. It’s funny how even Bart and Lisa point out a few plot holes at the end, only for their questions to be waved away without any answers.
Funny moments include Grandpa Simpson trying to take pride in his son during a performance, the joke about The Be Sharps’ name, and the items that Homer takes for worthless at the beginning of the episode. The best part might be when Homer tries to explain to Marge why he has to pretend he’s not married, making for a promising start to one of the show’s better seasons.
49. “Lisa on Ice” (Season 6, Episode 8)
IMDb Rating: 8.6/10
One of the greatest sports episodes of The Simpsons, Season 6’s “Lisa on Ice” pits Bart and Lisa against each other by way of a junior hockey season. When it turns out that Lisa is an outstanding goaltender, she joins Apu’s team and gradually becomes a confident phenom who’s ready to crush her brother’s team in the finals. Marge wants her children to feel proud no matter how well they play, but Homer’s philosophy overwhelms her efforts. He mocks whoever loses and rewards the winner, encapsulating the exact mentality an athlete should not have.
Who knew that an episode in which Lisa seemed incapable of doing well in any contact sport would demonstrate her prowess in one of the most physical sports around? Lisa’s character arc here is superb, but the dynamic between her and her brother is really what it’s all about. Despite Homer hilariously not learning a thing, the spectacular climax comes down to a shootout—and it couldn’t be more wholesome (the crowd’s behavior notwithstanding).
48. “Itchy and Scratchy Land” (Season 6, Episode 4)
IMDb Rating: 8.6/10
“Itchy and Scratchy Land” has got to be one of the most action-packed stories in The Simpsons. While most episodes might have a single short of the homicidal cat-and-mouse duo, this one has several; it even has the Simpson family visit the Itchy and Scratchy Land theme park. Now, since Krusty is one of the most grossly negligent characters in the series, there’s bound to be something that goes terribly awry. The robots that march through the park inevitably turn bad, and fans of the show wouldn’t have it any other way.
“Itchy and Scratchy Land” should be able to satisfy anyone in the mood for lots of cartoon violence and a good amount of humor along the way. Who knew that Bort was such a common name? And that helicopter ride into the theme park is still one of the highlights of season six. There aren’t that many episodes centered around Itchy and Scratchy, but this entry makes the case that there ought to be more.
47. “Homer Loves Flanders” (Season 5, Episode 16)
IMDb Rating: 8.6/10
Homer usually hates his neighbor Ned Flanders, but that’s about to change in season five’s “Homer Loves Flanders.” When Flanders invites Homer to a football game, Homer has such a stellar time that he goes out of his way to be Flanders’ friend. Unfortunately for this nice neighborino, Mr. Simpson is going to get on his nerves pretty quickly—making this one of the precious episodes to display the classic Flanders getting genuinely ticked off.
Shelbyville spiking the water supply, Mr. Burns’ demented strategy for inspiring a football team, and Homer getting mistaken for a homeless man are three fantastic moments in one of the season’s stronger episodes. There’s also the great revelation about what Moe does in his free time, the famous image of Homer creepily receding into a bush, and the marvelous car chase that pays perfect homage to Terminator 2: Judgment Day.
46. “Homer Goes to College” (Season 5, Episode 3)
IMDb Rating: 8.6/10
It’s been shown time and again that Homer sucks at his job, having neither the necessary education nor the interest in acquiring it. Season 5’s “Homer Goes to College” even begins with nap time at the power plant, something that fans might have only previously thought was something Homer did exclusively. It’s great when Mr. Simpson and those two other guys wind up guarding a bee during the inspection, and Homer making the van melt despite it not even containing nuclear material is top-shelf.
Instead of doing the simple thing and firing him for dangerous incompetence, the powers that be force him to try and get an education instead. Homer’s obviously never gone to college before, so his conception of how to behave is comically inaccurate. Aside from “pranks” that should get him not only expelled but arrested, other memorable moments include Grandpa being stuck in the car and a student who’s so pee-shy that he can’t go when someone knocks on the door.
45. “Homer’s Triple Bypass” (Season 4, Episode 11)
IMDb Rating: 8.6/10
Homer’s poor eating habits and less-than-desirable stature have been a constant presence throughout the entirety of the series, yet “Homer’s Triple Bypass” directly addresses the implications of Homer’s health. The episode sees Homer’s health finally catching up to him after he receives a heart attack on the job, soon taken to the hospital to find a solution. Dr. Hibbert soon informs the Simpsons family that Homer will need an expensive artery bypass surgery, eventually reaching a point where they must go to the sketchy Dr. Nick to get the surgery cheap.
It was seemingly inevitable that an episode of The Simpsons would tackle the often uncomfortable and all too real topic of heart disease and obesity, as it has been a central part of Homer’s character since the beginning. While it certainly has its comedic jabs at the expense of Homer, the episode also treats the terrifying nature of heart problems with the utmost severity, finding an effective balance that makes the episode a fan-favorite.
44. “Trilogy of Error” (Season 12, Episode 18)
IMDb Rating: 8.6/10
When it comes to anthology episodes in The Simpsons, many are quick to tout the exceptional Treehouse of Horror series of episodes, yet one of the best anthologies not a part of the Halloween specials comes in the form of “Trilogy of Error.” The episode follows three different stories each taking place on the same day, where Bart, Lisa, and Homer all have their own wild ventures that intertwine in strange ways. Homer is in a rush to the hospital to re-attach a severed thumb, Lisa is rushing to school so that she can win the science fair, and Bart has an ongoing scheme involving illegal fireworks.
While many other anthology stories keep each segment separate from one another and disconnected, the small connections and overlap are what make the stories of “Trilogy of Error” so effective. As more information is given with each subsequent story, more context and layers are added to the previous stories, with all of them coming together to create a cohesive and effective interconnected story. The epilogue is also highly effective at tying everything together for a comical and succinct ending.
43. “Stark Raving Dad” (Season 3, Episode 1)
IMDb Rating: 8.6/10
Infamous for being a banned episode of The Simpsons that even now isn’t available on Disney+, “Stark Raving Dad” provides some of the most wholesome and emotional moments of the entire show. The episode sees Homer being sent to a mental health facility for wearing a pink shirt to work, where he ends up making an unexpected friend in the form of Leon Kompowsky, who claims that he is Michael Jackson. Once he gets out of the institution, Bart ends up spreading the word around Springfield that the real Michael Jackson is coming to the Simpsons household.
It’s a genuine shame that this all-timer episode isn’t more widely available due to its inclusion of Michael Jackson as a guest star, as it features many exceptional jokes and one of the best endings in the series. Leon’s song that he sings to Lisa for her birthday is a standout moment from the early seasons of the show, showing that beneath all of the troubles and mischief that the Simpson family gets up to, they still deeply care about one another at the end of the day.
42. “Lisa’s Substitute” (Season 2, Episode 19)
IMDb Rating: 8.6/10
Widely considered to be one of the best Lisa episodes of The Simpsons, “Lisa’s Substitute” cuts to the very core of Lisa’s love of academics and how her family fails to understand her. The episode sees Lisa’s regular teacher, Miss Hoover, taking medical leave, bringing in a substitute teacher Mr. Bergstrom (Dustin Hoffman), who proves to be an unexpected hit among Lisa and her classmates. Bergstrom proves to introduce a new type of fun and excitement that can be had from learning, and while Lisa is devastated when Bergstrom has to leave, she learns that she can find role models in other people in her life.
“Lisa’s Substitute” tackles the all too effective and relatable message of having to say goodbye to those we love, as well as accepting those around us and finding a positive spin on the world no matter how sad things may be. It’s a beautifully heartwarming experience that makes for one of the strongest emotional cores that the series has ever seen, filled with iconic moments and a top-notch ending. The episode’s side-story about Bart running for class president also has its own array of great comedic moments, coming together to make an all-time episode.
41. “A Star is Burns” (Season 6, Episode 18)
IMDb Rating: 8.6/10
While The Simpsons finds itself crossing over with other adult animated series like Family Guy and Futurama much more frequently, the early seasons of the show only had one notable crossover with another adult animated series. “A Star is Burns” sees The Simpsons crossing over with the forgotten 90s cartoon The Critic, with Jay Sherman being invited to Springfield to act as a judge for a film festival. The festival proves to have many great and exciting works from the residents of Springfield, including a touching introspective about alcoholism from Barney Gumble.
While audiences of the time were divided on how to approach such a blatant crossover episode with another, much less successful animated series, time has certainly been kind to “A Star is Burns”. It largely helps that Jay Sherman and his style of humor feels perfectly in line with the world of The Simpsons, to the point where audiences may not even realize he’s from another show. The crossover is also only the jumping-off point for the episode, as the core surrounding the film festival provides many exceptional gags as well as great inflection into the citizens of Springfield.
40. “Homie the Clown” (Season 6, Episode 15)
IMDb Rating: 8.6/10
Acting as a deeper dive into one of the show’s most beloved and iconic side characters, “Homie the Clown” sees Homer becoming a Krusty the Clown impersonator, pretending to be him for birthday parties and other such local occurrences. Eventually, it becomes apparent that pretending to be Krusty has its fair share of positives, as the people of Springfield treat him better when they believe he’s Krusty. However, it soon gets taken too far when he gets kidnapped by the Mafia, who have been searching for Krusty since he is indebted to them.
“Homie the Clown” is a classic example of the many ups and downs of a signature Homer scheme and antics, seeing the blissful highs and perilous lows of Homer’s new lifestyle. Especially for a character who is rife with such comedic potential and iconic moments as Krusty, the episode fully delivers on the character’s comedy and brings him to the front. Even outside of the jokes that are directly tied to Krusty or clowns, there are a lot of iconic and classic jokes throughout the episode that have helped it stand the test of time.
39. “The Mysterious Voyage of Our Homer” (Season 8, Episode 9)
IMDb Rating: 8.6/10
In one of the most visually enthralling and metaphysical episodes of the entire series, “The Mysterious Voyage of Our Homer” sees Homer competing in a chili-eating contest, eating massive amounts of hot peppers after coating his tongue in hot wax. After winning the competition, he finds himself experiencing increasingly wild hallucinations, where he is seemingly guided through his mind by a Coyote (voiced by Johnny Cash).
The episode already reaches its high status thanks to the magical and mystifying visuals of Homer’s hallucination journey, but what also helps the episode become an icon of the series is its themes of true love and alcohol use. It’s one of the best episodes when it comes to establishing and solidifying the love between Homer and Marge as soulmates and perfect matches for one another, despite their many differences and occasional arguments. Cash also does a great job voicing the alluring and calming Coyote who helps Homer along his wild journey in the spirit world.
38. “Boy Scoutz ‘n the Hood” (Season 5, Episode 8)
IMDb Rating: 8.6/10
A great showcase of just how quickly and comedically the stakes can be raised in a singular episode, “Boy Scoutz ‘n the Hood” sees Bart having accidentally signed up for the Junior Campers after a sugar rush night on the town. He decides to stick it out in order to get out of pop quizzes, and reluctantly, Homer joins Bart on a father-son rafting trip with Ned and Rod Flanders. The group accidentally finds themselves separated from the rest of the campers and eventually even lost at sea, being stranded in the middle of the ocean blue for what seems like days on end.
The relationship and connection between Bart and Homer is one that is always touched upon and building throughout the show, with this episode being a great self-contained reflection of how the duo grow and learn from one another. This is on top of the many great moments throughout the episode, from Bart and Milhouse’s ‘Springfield, Springfield’ musical number to the comedic wallowing of the group while they are lost at sea.
37. “Bart the Murderer” (Season 3, Episode 4)
IMDb Rating: 8.6/10
Bart always seems to find himself in precarious situations as the quintessential troublemaker of the Simpsons family, with no episode showing this off quite like “Bart the Murderer/” The episode sees Bart wallowing after a bad day at school, where he discovers and gets hired at a local Mafia club as a bartender. However, after relaying his sorrows of the day to the mafia bar’s patrons, Principal Skinner suddenly ends up missing, with Bart now acting as the prime suspect and put on trial for his assumed murder.
“Bart on trial for murder” is such a simple yet perfect premise for the show, and the episode is able to perfectly make the most out of its exceptional premise and the dynamics and characteristics of Bart in the court of law. The episode finds great inspiration not only from classic crime movies, but also classic court dramas in making the most hilarious and memorable portrayals of the Simpsons Mafia and Fat Tony in the series.
36. “Bart on the Road” (Season 7, Episode 20)
IMDb Rating: 8.6/10
Ironically, despite its title, “Bart on the Road” easily makes for one of the series’ best outings for not just Bart, but his entire group of friends and classmates, including Milhouse, Martin, and Nelson. The episode sees the quartet on a wild road trip across the country after using a fake driver’s license to rent a car at the DMV. It soon becomes up to Lisa to chase the group down in an attempt to get them to return home, all while they experience the wild wonders of the country and personal growth on their trip.
While many episodes are quick to write off Milhouse, Martin, and Nelson as simple background characters who are given a joke or two per episode, “Bart on the Road” provides them with real character traits and development, fully fleshing them into memorable characters. It works great for the episode’s singular coming-of-age adventure, creating an experience that finds clear inspiration from classic coming-of-age films of the era.
35. “$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling)” (Season 5, Episode 10)
IMDb Rating: 8.6/10
“$pringfield” sees the fallout following the city of Springfield’s legalization of gambling to revitalize the economy, leading to Mr. Burns opening a high stakes casino where Homer is hired as a blackjack dealer. At the same time, Marge ends up developing a gambling addiction, Bart opens his own, smaller-stakes casino in his tree house, and the ongoing struggle of running a casino proves itself to become a toil on Mr. Burns’ mental state.
“$pringfield” is an exceptional example of an episode that allows the entire Simpson family to shine in their own stories, as opposed to primarily centering on a singular family member or character in the story. Each member of the family, as well as an array of other characters, have their changes and reactions to the legalization of gambling, each with inherent comedy strewn throughout. While the episode has an effective message about the dangers of gambling, it features a great deal of comedic absurdity to get this point across.
34. “Treehouse of Horror VI” (Season 7, Episode 6)
IMDb Rating: 8.6/10
One of many legendary Treehouse of Horror episodes of the series, “Treehouse of Horror VI” features some of the most beloved and iconic segments in the entire series. In the first segment, Springfield finds itself being terrorized by an army of dangerous giant evil advertisements. The second segment is a direct parody of A Nightmare on Elm Street, with Groundkeeper Willie taking on the villainous role of Freddy Krueger. The third and most iconic segment sees Homer getting stuck in a strange 3D world, before eventually ending up stuck in the real world.
Treehouse of Horror episodes have become famous in themselves even outside of the show for just how hilarious, iconic, and inventive they take their parodies and premises. “Treehouse of Horror VI” is easily one of the best Treehouse of Horror episodes in the series, with the Nightmare on Elm Street segment especially being widely praised and in contention for the best segments in the show’s history.
33. “Bart’s Comet” (Season 6, Episode 14)
IMDb Rating: 8.7/10
“Bart’s Comet” sees the outcry and consequences following Bart’s miraculous discovery of a comet, which scientists soon theorize is heading straight for Springfield in a collision course. Several of Springfield’s residents have their solutions and ways of dealing with the news, ranging from ineffective ways to stop the comet to simply leaving town or hunkering down in a shelter. The Simpson family soon finds themselves taking refuge in Flanders’ bomb shelter, but nearly the entire city finds themselves crowding the shelter to its maximum occupancy.
“Bart’s Comet” is a simple and timeless premise pulled off masterfully by the show, able to get a great deal of mileage out of the inherent dread and dark comedy of the situation. There are countless memorable and iconic jokes and sequences throughout the episode that has made it a widely beloved and appreciated episode with time, as well as one of the best episodes of the golden era of the show.
32. “Bart of Darkness” (Season 6, Episode 1)
IMDb Rating: 8.7/10
The Simpsons‘ own rendition of the cinematic classic, Rear Window, “Bart of Darkness” sees Bart confined to his room after breaking his leg, leaving him stuck and unable to socialize with anyone. He soon finds enjoyment in observing the outside world through a telescope gifted to him by Lisa, but it doesn’t take long before Bart begins to suspect that Ned Flanders murdered his wife, Maude. The episode’s b-plot sees Lisa dealing with the consequences of being the new center of popularity following the installation of a pool in the family backyard.
“Bart of Darkness” is easily one of the best Bart episodes in the entire series, giving the character the room and opportunity to expand and cover all angles while he’s stuck in his room. While the character has always been a bit of a troublemaker, seeing him spring into action to do what’s right paints a great picture of his true character and honesty, even if his assumptions are misleaded. Even outside the strengths surrounding Bart himself, the episode is a great parody of an Alfred Hitchcock classic, with enough distinct Simpsons charm to make it feel like its own standalone experience.
31. “Lemon of Troy” (Season 6, Episode 24)
IMDb Rating: 8.7/10
While mostly forgotten in the later seasons thanks to the increased focus on Springfield, “Lemon of Troy” is easily the series’ best example of their endless rivalry with their neighboring city, Shelbyville. In the episode, a group of Shelbyville kids steal Springfield’s sacred lemon tree, which entices Bart and his friends to go on a high-stakes heist into the city to take it back. It soon turns into a Mad Max-style chase where nearly all of Shelbyville is chasing down Bart and his friends.
As far as consistent and episode-long parodies go, “Lemon of Troy” is an easy stand-out in the series, finding great deals of comedy from having such major stakes surrounding something as trivial as a lemon tree. The episode itself, on top of having exceptional action and humor, has a great core message and themes about the importance of history and stories being passed down from generation to generation, as well as just how easy it can be to muddle the truth over time.
30. “Mother Simpson” (Season 7, Episode 8)
IMDb Rating: 8.7/10
“Mother Simpson” starts with Homer enacting a scheme to fake his death to get out of work, a plan that inadvertently has him learn that his mother, who he presumed to have died 26 years ago, is still alive. After an emotional reunion where Mona Simpson meets the rest of the family, it becomes increasingly apparent that she is harboring a mysterious secret that may just be the reason why she left and never returned. One thing leads to another, and she ends up being chased off by the FBI, once again leaving Homer’s life.
“Mother Simpson” may just feature the most iconic singular ending in an episode of the show, with its signature shot of Homer looking up at the night sky that forever impacted a generation. It acted as the perfect climax to an already emotionally resonating episode, thanks to the great guest performance by Glenn Close as Mona Simpson, who helps bring home this tear-jerking story of Homer’s short reunion with his long-lost mother.
29. “Lisa’s First Word” (Season 4, Episode 10)
IMDb Rating: 8.7/10
One of the most emotional episodes in the sitcom’s history, “Lisa’s First Word” is a flashback episode following many attempts to get Maggie to speak her first words. It conjures up the story of how Lisa said her first words, telling the heartfelt story that would begin before Lisa was even born, and the jealousy and resentment that Bart was beginning to form for having to share his life with a sibling. However, the episode has an emotionally poignant ending that makes for one of the best moments in the show’s history.
As opposed to many other Simpsons episodes where the primary draw is inherent comedy and hijinks, the biggest draw of “Lisa’s First Word” is its powerful heartwarming energy. It provides much greater context into the relationships and undeniable love in the Simpsons family between siblings, telling a powerful story that no matter how things may appear, the bonds of family are forever strong.
28. “Hurricane Neddy” (Season 8, Episode 8)
IMDb Rating: 8.7/10
More commonly recognized as the episode where Ned Flanders snaps at everyone in Springfield, “Hurricane Neddy” sees the town coming together to rebuild Ned’s home after it was taken out by a hurricane. However, the shoddy reconstruction of the house has Ned boil over in rage, completely laying into the flaws and failures of everyone in Springfield after years of being the kindhearted neighbor. He then commits himself to a mental hospital, bringing into question the repressed problems from his childhood that caused him to become this way.
“Hurricane Neddy” is a clear example of a great Simpsons episode that doesn’t center around a member of the family, with a great deal of the focus and perspective being on Ned and his struggles. Ned Flanders was already such a beloved and iconic character in the show’s history, with this episode only further going into detail and scope into the inner struggles and process of the most iconic neighbor in television history.
27. “Homer at the Bat” (Season 3, Episode 17)
IMDb Rating: 8.7/10
“Homer at the Bat” sees Homer and the rest of his co-workers joining the plant’s softball team, managing to bring the team to great success, putting them in the finals against their rivals, the Shelbyville Power Plant team. However, the stakes find themselves to be astronomically raised when Mr. Burns makes a million-dollar bet that his team will win, and in order to secure victory, Burns hires a full MLB team to play instead.
“Homer at the Bat” is easily the ultimate Simpsons episode for baseball fans, with numerous stellar cameos of the era’s biggest players, as well as a great deal of classic sports shenanigans. Even outside of these appearances, the episode is chock-full of great comedic moments, as well as effective stakes, as the game with Shelbyville grows closer and closer, absolutely down to the wire. It’s without a doubt the best sports episode that The Simpsons has ever seen.
26. “Homer the Smithers” (Season 7, Episode 17)
IMDb Rating: 8.8/10
“Homer the Smithers” provides a closer look into the work relationship between Homer and his notoriously evil boss, Mr. Burns, following Homer as he is appointed as the temporary replacement to Smithers. This results in a wide number of comedic hijinks, as Homer attempts to do his best to do a great job to Mr. Burns for the sake of his own job prospects, to the point of being overworked. It’s all the more ironic because the only reason that Smither chose Homer to be the replacement was that he knew that Homer wouldn’t outshine him and the work he’d done while on vacation.
The episode is easily one of the show’s brightest showcases of the undeniable bond between Mr. Burns and Smithers, two of the most iconic side characters in the show’s history. The episode also features its fair share of genuinely emotional moments, as Homer’s dedication and self-destruction for the sake of his job and his family is commendable, and it’s easy to feel for him with just how comically strict Burns’s demands are.
25. “Bart Sells His Soul” (Season 7, Episode 4)
IMDb Rating: 8.8/10
In the Season 7 episode “Bart Sells His Soul,” a doubtful and arrogant Bart impulsively sells his soul to his best friend Milhouse for five dollars, ridiculing anyone who points out its importance. While Bart doesn’t think much of it initially, he begins to doubt his own beliefs after a series of strange occurrences point to the existence of the soul. Bart soon fears the consequences of his actions and tries to take it back.
“Bart Sells His Soul” proves that existentialist themes can be explored beyond film, with the show cleverly addressing philosophical and spiritual subjects while still delivering plenty of laughs. The episode’s writer Greg Daniels was actually inspired by a childhood experience where he “bought” a bully’s soul, making Bart’s story even funnier since it’s rooted in reality.
24. “Treehouse of Horror IV” (Season 5, Episode 5)
IMDb Rating: 8.8/10
Any fan of the series is likely familiar with the Halloween-themed Simpsons episodes, with “Treehouse of Horror IV” among the greatest ones. In the first segment, “The Devil and Homer Simpson,” Homer sells his soul to the devil, who looks suspiciously like Ned Flanders, for a donut. In “Terror at 5½ Feet,” Bart discovers a gremlin dismantling the school bus during a stormy ride. Finally, in “Bart Simpson’s Dracula,” the Simpsons visit Mr. Burns’ mansion and become the target of his vampire ambitions.
With clever references to shows and movies like The Twilight Zone, Bram Stoker’s Dracula, and The Lost Boys, “Treehouse of Horror IV” was on point for its time and quickly became a popular episode. The decision to have Flanders show up as the devil was a particular stroke of genius, which was topped by Homer’s gut-busting decision not to eat the last bit of his donut to save his soul from eternal damnation.
23. “Rosebud” (Season 5, Episode 4)
IMDb Rating: 8.8/10
Some episodes of The Simpsons showcase a more human side to the usually villainous and inhumane Mr. Burns, with “Rosebud” arguably being the best of those. A Season 5 classic, the episode follows Mr. Burns who, after seeing a nostalgic documentary about his life, becomes obsessed with taking back his childhood teddy bear, Bobo. However, Bobo is now owned and deeply loved by Maggie – Mr. Burns goes to great lengths to change this.
Aside from Maggie being adorable, the episode is memorable for Homer’s refusal to give up Bobo. Despite sealing a sweet deal for Mr. Burns giving him “a million dollars and three Hawaiian Islands” just for the ratty old bear, Maggie’s sad face is enough for Homer to call it off. As expected, the episode also escalates to some absurd levels, blending humor with emotional nostalgia.
22. “One Fish, Two Fish, Blowfish, Blue Fish” (Season 2, Episode 11)
IMDb Rating: 8.8/10
“One Fish, Two Fish, Blowfish, Blue Fish” sees Homer panicked after having eaten a poisonous fugu fish at a sushi restaurant. He’s told that he only has 24 hours to live, so he decides to make the most of it by making a list of things he wants to do before his death. Facing his fears, Homer embarks on this bucket list-style quest… only to get caught speeding and put in jail.
The Season 2 episode is an excellent example of tragicomedy on the small screen, with Homer’s plight being unsurprisingly rooted in existential and philosophical ideas. It’s also just a great episode because of the way it captures Homer’s character in general, as if giving viewers a picture of his life up to that point. Oh and spoiler alert, he doesn’t die.
21. “Mr. Plow” (Season 4, Episode 9)
IMDb Rating: 8.8/10
In “Mr. Plow,” Homer becomes a local hero after buying a snow plow and starting his own snow removal business, mostly helping his neighbors clear their driveways. His sudden success soon leads to a rivalry with his friend Barney, who also starts a snow plow business and competes with Homer for customers. Barney eventually puts Homer out of business, leading to more friction between the drinking buddies.
“Mr. Plow” is crucial for The Simpsons for many reasons, one of them being that Dan Castellaneta won an Emmy Award for “Outstanding Voice-Over Performance” for this episode. The Season 4 episode is also notable for the way its narrative and characters look and feel more like the classic Simpsons that fans would come to know and love. “Mr. Plow” feels like a turning point for the show that has finally found its footing and has more refined characters that would go on to become iconic.
20. “Homer’s Phobia” (Season 8, Episode 15)
IMDb Rating: 8.8/10
An award-winning episode featuring the voice (and likeness of) filmmaker John Waters, “Homer’s Phobia” revolves around Homer’s decision-making after discovering that his new family friend John (Waters) is gay. He soon takes Bart hunting just to further dissociate himself from John and embrace the more “masculine” activities he and his son can bond over. Of course, things soon go very wrong.
The episode was controversial when it first premiered, as its anti-homophobia message and new character sparked debates among viewers. It managed to be a biting satire and a Simpsons episode that thoughtfully explored LGBTQ+ issues while still being wildly entertaining (and worth watching more than once).
19. “Homer vs. the 18th Amendment” (Season 8, Episode 18)
IMDb Rating: 8.8/10
“Homer vs. the Eighteenth Amendment” showcases the wacky events that follow Springfield’s enactment of a prohibition as a consequence of a too-rowdy Saint Patrick’s Day celebration. To counteract this, Homer and his friends start a speak-easy (Moe’s) and he soon takes on the persona of the Beer Baron.
A classic Simpsons episode, there’s no shortage of things to love about it. Aside from the hilarious hijinks courtesy of Homer and the gang, the episode actually shows a rare situation where Homer uses his intelligence to solve a problem, adding to the hilarity of the premise. Anything for beer!
18. “Flaming Moe’s” (Season 3, Episode 10)
IMDb Rating: 8.8/10
In “Flaming Moe’s,” Homer tells the titular bartender about his newest invention – a bizarre cocktail with fire and medicine guaranteed to catch people’s attention. When Moe steals this recipe and claims it as his own, Homer becomes enraged and vows he’ll get payback.
The episode is best remembered for its obvious parody of the iconic long-running live-action sitcom Cheers, with the opening sequence “Where Everybody Knows Your Name” paralleled for Moe’s Tavern. More importantly, it’s the first episode that really focuses on Moe Szyslak’s personality and motivations (thankfully the first of many).
17. “Deep Space Homer” (Season 5, Episode 15)
IMDb Rating: 8.9/10
A crucial episode in The Simpsons, “Deep Space Homer” marked an important moment in the direction the series would go in the future. The episode follows Homer’s wacky space adventure after he’s selected by NASA to participate in a spaceflight. While on the shuttle, he unsurprisingly causes some catastrophic but hilarious events.
Aside from being a witty parody of 2001: A Space Odyssey, the episode is memorable because it marked The Simpsons’ decision to dive deeper into absurd humor. No longer confined to the town of Springfield, it would signal the start of many out-of-this-world misadventures for the beloved characters. There’s also the fact that the episode’s guest stars include Apollo 11 astronaut Buzz Aldrin and musician James Taylor.
16. “And Maggie Makes Three” (Season 6, Episode 13)
IMDb Rating: 8.9/10
In one of the most emotional and iconic Simpsons episodes ever, Homer explains to Bart and Lisa why there are no baby pictures of Maggie in their family albums. He tells them about how he saved up and quit his job at the power plant to apply for his dream position at a bowling alley, but when Marge becomes pregnant, he has to make some tough choices.
“And Maggie Makes Three” is known for its tear-jerking ending, which shows how Homer covered the large plaque Mr. Burns placed near his desk, which originally read “Don’t forget: you’re here forever.” After falling in love with Maggie after she was born, those letters would soon be covered with her baby pictures to reveal the words “Do it for her.”
15. “Homer the Heretic” (Season 4, Episode 3)
IMDb Rating: 8.9/10
The Simpsons established itself as an animated series for mature viewers early on, especially through episodes like “Homer the Heretic.” The episode depicts Homer’s string of good luck after deciding to stay home on a Sunday instead of going to church with the rest of his family. Instead, he enjoys dancing around in his underwear, making his special waffles, finding a penny, and more. When he decides never to go back to church again, God pays him a visit.
A fantastic example of how the series presents social commentary in humorous ways, the Simpsons episode highlights the absurd obsession with religion and conformity (and the social repercussions of choosing otherwise).
14. “22 Short Films About Springfield” (Season 7, Episode 21)
IMDb Rating: 9.0/10
A loose parody of Pulp Fiction, “22 Short Films About Springfield” is an episode with a title that reveals the entire plot. It portrays a variety of Springfield’s residents – Bart and Milhouse, Apu, Mr. Burns and Smithers, Moe, and more – experiencing their own little stories that are soon revealed to be interconnected.
The Simpsons episode is a wonderful view into the lives and personalities of the characters fans know and love. Each story is creative and entertaining, from Principal Skinners’ disastrous roast and Lisa’s hair issue to Bart’s daring prank and Chief Wiggum’s conversation about McDonald’s.
13. “Who Shot Mr. Burns? Part Two” (Season 7, Episode 1)
IMDb Rating: 9.0/10
As Mr. Burns lies in the hospital with a gunshot wound, the investigation into his attempted murder gets intense. Everyone in Springfield has a motive, but when Chief Wiggum relies on an Agatha Christie novel to guide him, things don’t go well until Simpson DNA turns up on Burns’ suit.
This episode opens with Burns in Smithers’ shower, and for a moment, fans are led to believe it’s all been just a dream, reminiscent of Dallas’ infamous cliffhanger. Sideshow Mel pulls a Sherlock Holmes, Lisa speaks in Twin Peaks tongue, and Groundskeeper Willie channels Sharon Stone in Basic Instinct. To keep the ending from leaking, several alternates were animated, some of which aired during “The Simpsons 138th Episode Spectacular!,” including Apu, Barney, Smithers, and Santa’s Little Helper as the gunmen.
12. “The City of New York vs. Homer Simpson” (Season 9, Episode 1)
IMDb Rating: 9.0/10
On Barney’s turn as designated driver, Duffman shows up with bottomless beer. This breaks poor Barney; when he drops Homer off that night, he disappears with the Simpson car, leaving it illegally parked at the World Trade Centre for two months. While the rest of the family goes sightseeing in NYC, Homer has to wait by his car from 9 to 5, though some clam juice derails his best intentions.
Fans love this episode – which comes from one of the best seasons of The Simpsons – for the pickled egg draw, Homer’s Flushing Meadows fantasy, the parking enforcement department that only hires Steves, Marge’s humble dream “of being in a Broadway audience,” and Bart’s visit to MAD Magazine. This episode was removed from syndication after 9/11 but went back into rotation in 2006 with some scenes edited out. Producers later donated a hand-drawn cel from the episode to the National September 11 Memorial & Museum.
11. “Last Exit to Springfield” (Season 4, Episode 17)
IMDb Rating: 9.0/10
Eight-year-old Lisa needs braces. It’s bad timing since the power plant has just nixed the union’s dental plan in favor of a beer keg at all their meetings. Instead of braces, Lisa gets a headset that predates stainless steel, “so you can’t get it wet.” Homer takes over as union president and goes head-to-head with Mr. Burns, leading the plant employees on strike.
The episode’s most memorable elements include Grampa’s pointless story, Lisa’s protest song, Mr. Burns’ likeness to The Grinch, the horrifying Big Book of British Smiles, and the first of many gags involving Burns’ never remembering who Homer Simpson is. The Simpsons episode is an ode to activism and the power of united workers.
10. “King-Size Homer” (Season 7, Episode 7)
IMDb Rating: 9.0/10
When Mr. Burns enacts a required morning calisthenics program at the nuclear power plant, Homer does whatever he can to get out of it. In “King Size Homer,” fans watch as he embarks on a dangerous journey to qualify as disabled by eating enough food to increase his weight to 315 pounds. Once he does, Homer finally gets what he wants and is allowed to work from home, which soon turns into his worst nightmare.
Highlighting the show’s signature satire and wit, the episode from one of the best Simpsons seasons prods at the prevalent obsession with weight in pop culture. It also has some gut-busting and unforgettable moments like Homer’s donning of a bright muumuu and his climactic jump.
9. “Homer the Great” (Season 6, Episode 12)
IMDb Rating: 9.0/10
“Homer the Great” revolves around the ancient group known as the Springfield chapter of the Stonecutters, which Homer joins after feeling envious of Lenny and Carl. Things predictably go wrong when Homer destroys one of their sacred items, which leads to his exile. But, Homer’s rare birthmark soon doesn’t just get him a way back in, but brings him to the very top.
The wacky episode of The Simpsons pokes fun at secret societies and elite groups in general in absurdly hilarious ways. A searing critique of groupthink and the strange things people will do to be part of the “it crowd,” it’s a fan-favorite episode for a reason (that’s still relevant today).
8. “Homer Badman” (Season 6, Episode 9)
IMDb Rating: 9.0/10
A misunderstanding with their new babysitter Ashley puts Homer in an awful situation in “Homer Badman.” After the babysitter, who is also a feminist graduate student, mistakes Homer’s drooling for candy as a sexual advance, the Simpsons’ lives are turned around by the ensuing media frenzy around the case.
Certainly one of The Simpsons‘ more daring social commentaries, the episode critiques media sensationalism and highlights its effects on once-unknown citizens (like the goofy but likable Homer Simpson). It does so with the same humor, wit, and absurdity that the series has become known for at this point.
7. “The Springfield Files” (Season 8, Episode 10)
IMDb Rating: 9.1/10
After scoring “Boris Yeltsin” on the breathalyzer test, Homer attempts to walk home, but crossing through a spooky forest; he encounters an alien. The glowing creature tells him, “Don’t be afraid,” which has the opposite effect on Homer. Agents Mulder and Scully (of The X-Files) visit Springfield (with Gillian Anderson and David Duchovny providing voices) to investigate Homer’s claims.
Fans remember this one fondly for Red Tick Beer which “needs more dog,” Chief Wiggum’s invisible typewriter, a turtle wearing Grampa’s teeth, and a cameo by the Cigarette Smoking Man. “The Springfield Files” is positively bursting with sci-fi references, including Close Encounters of The Third Kind and E.T. An alien lineup includes Marvin the Martian, Gort from The Day The Earth Stood Still, Chewbacca from Star Wars, ALF, and either Kang or Kodos, which producer Mike Reiss calls the most illegal shot in the show’s history.
6. “Marge vs. The Monorail” (Season 4, Episode 12)
IMDb Rating: 9.1/10
Mr. Burns is forced to pay a $3 million polluter’s fine, and Springfield gets to decide how they’ll spend this sudden influx of cash. Marge has the town enthused to finally fix up Main Street when in walks Lyle Lanley (voiced by Phil Hartman). After a very catchy song and dance number, the town impulsively buys a monorail from him. Lanley’s hasty training and random appointment of Homer as conductor leaves Marge to save Springfield from its dangerous new investment.
Written by Conan O’Brien, this episode was instantly embraced by both fans and critics. It continues to be beloved due to its Flintstones-inspired opening, a spectacular Simpsons musical number, a surprising cameo by Leonard Nimoy, iconic details such as the popsicle stick skyscraper and the escalator to nowhere, and memorable lines like “I call the big one Bitey.”
5. “You Only Move Twice” (Season 8, Episode 2)
IMDb Rating: 9.2/10
After consulting absolutely no one, Homer moves his family to another town to take a better job. His new boss, Hank Scorpio (voiced by Albert Brooks), delivers perks and praise effusively, and Homer’s team is competent enough to make him look good at his job. It’s really the perfect situation, except Marge is miserable with no homemaking to do in their largely automated house, Bart is sent to a remedial class, and Lisa is allergic to the whole town.
In what is almost the best Simpsons episode, Brooks’ Scorpio is a legendary one-off character, and much of the episode’s humor is derived from the fact that Homer doesn’t seem to realize his boss is actually a Bond villain. Fans are fond of Bart’s slow Canadian classmate, the illustrious hammock district, Lisa’s chipmunk encounters, and the scathing Denver Broncos burn. “You Only Move Twice” is a fantastic Bond parody and an unforgettable Simpsons episode.
4. “Who Shot Mr. Burns? Part One” (Season 6, Episode 25)
IMDb Rating: 9.2/10
While burying class pet Super Dude, Willie strikes oil, and Springfield Elementary is suddenly very, very rich. Mr. Burns burns with jealousy until he finds a way to trick the kids and steal the oil, making him greedier. Ready to take on his greatest enemy yet, the sun, he invests his profits in a sun-blocking machine which will make his power plant all the more necessary.
At yet another productive town hall meeting, most of the residents are stroking guns and plotting revenge. When Mr. Burns winds up shot at the end of the episode, nearly everyone’s a suspect. Never excluded from any discussion of The Simpsons‘ best episodes, “Who Shot Mr. Burns” is peppered with clues about who the killer will be, and savvy viewers searched diligently via freeze-frame.
3. “Treehouse of Horror V” (Season 6, Episode 6)
IMDb Rating: 9.2/10
In the show’s first vignette, a parody of The Shining sends Homer off the deep end when “No TV and no beer make Homer go crazy.” In Time and Punishment, Homer keeps traveling back in time and accidentally making the future worse. And in Nightmare Cafeteria, the teachers feast on kids sent to detention.
Throughout all three, a running gag sees Willie rushing in to save the day, only to immediately take an ax to the back. The perfect irony is achieved in the middle vignette when Homer rejects an otherwise wonderful world for its lack of donuts, only for the audience to learn that donuts fall from the sky. In what is considered one of the best Treehouse of Horror and funniest Simpsons episodes, fans loved seeing the Simpsons freeze to death, get lobotomized, and dance a skinless Broadway number, at least until Bart’s intestines are devoured by his best friend.
2. “Cape Feare” (Season 5, Episode 2)
IMDb Rating: 9.2/10
Bart’s been receiving death threats written in blood, and fans immediately suspect Sideshow Bob (Kelsey Grammer) even though he’s in prison. However, Blue Haired Lawyer is awfully convincing, and the parole board grants Bob clemency despite some pretty damning evidence from other people he’s tried to kill. The “Thompsons” go into witness relocation in Terror Lake, but a wily Bob is two steps ahead (or rather, hiding under their car).
This entire episode is a send-up to the 1962 film, Cape Fear; the “Thompsons” get their name from its director, J. Lee Thompson. When the episode proved a little short, Sideshow Bob’s rake gag was extended, making for an iconic Simpsons moment. Grammer is asked to sing almost every time he guest stars. In this episode, Bart saves his bacon by asking Bob to sing the score from H.M.S. Pinafore; Grammer sings this same excerpt in his sitcom, Frasier.
1. “Homer’s Enemy” (Season 8, Episode 23)
IMDb Rating: 9.3/10
In the highest-rated Simpsons episode, Frank Grimes is featured as a character who struggled for literally everything in his life, even studying science by mail to earn his degree in nuclear physics. Working alongside Homer, Grimes is repeatedly confronted by Homer’s laziness. He attempts to expose Homer’s idiocy by tricking him into competing in a children’s contest, but when Homer wins, Grimes has a meltdown, ultimately electrocuting himself to death while imitating Homer.
What makes “Homer’s Enemy” the best episode of The Simpsons to fans and critics alike is that it introduces a realistic person to Springfield. Homer is an acknowledged dolt, yet everyone in Springfield tolerates him as if his tremendous stupidity is just another quirk to be put up with. Grimes, however, holds up a mirror to Homer by being a professional with a strong work ethic. He is understandably resentful of Homer because he’s had to work so hard for the things Homer accidentally falls into. This is the most self-reflection viewers have seen from The Simpsons, and it was a compelling view.
