The Simpsons is one of the longest-running television shows of all time. With the recent final episode of the landmark 30th season, the show has produced 662 episodes and shows no signs of slowing down. Most fans and critics would agree that the show’s golden years have long since past and The Simpsons have somewhat outstayed their welcome. But let’s not forget that countless great episodes we’ve gotten over the years which made it one of the funniest shows of all time.
To go through all these episodes and determine which are the greatest is no easy task. But we feel we have created a solid list of the most entertaining and hilarious episodes in the show’s long history. Here are the best Simpsons episodes of all time.
Updated by Colin McCormick on April 2, 2020: We could all use a good laugh in these strange times as well as a great show to binge-watch. Luckily, The Simpsons offers both and 30 seasons of the beloved show are available on Disney+ right now. Given the historic run of the show, there are far more spectacular episodes to choose from. We’ve added some more great favorites to this list so you can continue to enjoy the best of the best of The Simpsons.
15 Homer’s Barbershop Quartet
Many episodes have explored the untold stories of Marge and Homer’s earlier days from their youthful romance to the birth of their children. However, “Homer’s Barbershop Quartet” relives Homer’s unexpected brush with fame with his old-timey musical group, The Bee Sharps.
The episode mixes the show’s talent for musical moments with a hilarious satire of the Beatles and their rise to success, as well as their eventual fall. The combination of Homer, Skinner, Apu, and Barney as the band is a perfect team and there’s even a great cameo from George Harrison.
14 The Itchy & Scratchy & Poochie Show
Itchy and Scratchy is the beloved cartoon within a cartoon that all of Springfield’s kids love so much. However, when the ratings for the show begin to dip, they decide to pull a cheap stunt by introducing a brand-new character, Poochie the dog. And, of course, Homer is hired to voice the new character.
The episode is a fun meta-commentary on cartoons as well as another one of Homer’s wacky adventures. The totally misguided creation of Poochie feels like something we’ve seen happen in many real shows, and it makes for a fun episode to explore.
13 El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)
Homer and Marge’s marriage has gone through more than its fair share of troubles, but none of them have been quite as trippy as we see in this hugely entertaining episode. After Homer makes a fool of himself at a chili festival, much to Marge’s frustration, he goes on a spiritual journey to find his soulmate.
The episode is not only a hilarious journey for Homer, but it features some truly great visuals. Another highlight is the wonderful guest-starring role by Johnny Cash as a talking coyote who serves as Homer’s spirit guide.
The Simpsons loves to reference and parody famous movies and sometimes even dedicate entire episodes to riffing on classics. “Rosebud”, of course, is a parody of Orson Welles’ Citizen Kane with Mister Burns as the central figure who is trying to regain some of his lost childhood via his teddy bear.
Anyone who has seen Citizen Kane will pick up on the countless jokes and references to the classic film. However, this episode functions just as well on its own merits as it hilariously takes a look at Burns and his past life.
11 Deep Space Homer
The show has taken on many outlandish adventures but sending Homer into space seemed like they might have finally gone too far. However, “Deep Space Homer” takes the ridiculous premise and turns it into one of the funniest and most entertaining episodes of the show.
From the first act that deals with Homer being unappreciated at work, to Homer and Barney’s NASA training, to the actual space adventure featuring Buzz Aldrin, the episode is a jam-packed saga filled with laughs and excitement.
10 Homer The Great (Season 6, Episode 12)
Any episode that let’s Homer shine is bound to be good for some laughs. After finding out about a secret society that many of his friends belong to called the Stonecutters, Homer weasels his way into the group. Of course, before long he offends everyone and is about to be banished, only to be discovered as the Chosen One.
Only someone like Homer Simpson could discover an ancient organization like the Stonecutters and ruin it so quickly. The episode is filled with great gags like the “No Homers Club”, a guest appearance by Patrick Stewart, and rousing musical number, all of which make for some great fun.
9 Who Shot Mr. Burns Part 1 (Season 6, Episode 25)
For a show to end their season on a cliffhanger can be a pretty cheap move. However, The Simpsons managed to pull it off in a hilarious and satisfying way. The episode focuses largely on Mr. Burns, one of the most evil and entertaining characters on the show. After stealing from the oil reserve found at Springfield Elementary, Burns makes many enemies in the town leading to one of them shooting him at the end of the episode.
From the school’s reaction to their newfound riches, to Homer’s frustration at being ignored by Burns, to Burns’ outlandish scheme to block out the sun, this episode felt like a big event with a conclusion we cliffhanger we were actually interested in.
8 22 Short Films About Springfield (Season 7, Episode 21)
With so many characters on the show, no one episode can do them all justice. However, this wild episode is the closest they have ever come. The entire episode is a collection of short stories involving some of Springfield’s most memorable characters as well as some of the background characters.
In one piece, Apu finally takes a much-needed and quick break from work. In another, various Springfield citizens try to help Lisa get gum out of her hair. There’s even a Pulp Fiction parody thrown in for good measure. It’s an excellent reminder of the amazing cast of characters the show has created over the years.
7 Homer At the Bat
The sports-themed episodes of The Simpsons are always a highlight and this one is certainly the best. After the Springfield Power Plant’s baseball team goes on a winning streak, Mr. Burns tries to secure the championship by filling to team with players from the Major Leagues, like Darryl Strawberry and Wade Boggs.
Surprisingly, it’s the baseball stars that steal the show here with some of the funniest moments. It’s great fun watching each of them sidelined by some strange predicament. It’s another great episode for Burns as well who takes an unorthodox approach to coaching.
6 Last Exit To Springfield (Season 4, Episode 17)
Despite making a career of being an undependable buffoon, Homer is often thrown into leadership roles in which he is in way over his head. After Burns gets rid of the Power Plants’ employee dental plan just as Lisa is in need of braces, Homer leads his fellow workers in a strike.
The episode is fondly remembered for Homer’s endless “Dental plan…Lisa needs braces” train of thought, but there are so many great aspects to the episode. The overly intense dentist, Burns’ attempts to intimidate the strikers and Homer’s perpetual fear of responsibility make for some hilarious moments.
5 Homer’s Enemy (Season 8, Episode 23)
Few characters have made such a lasting impact on The Simpsons with only one appearance as Frank Grimes. A professional and hard-working inspiration, Grimes finally gets himself a job at the Nuclear Power Plant where he is forced to work alongside Homer Simpson.
Immediately, Grimes recognizes Homer to be incompetent and is beyond frustrated by how life seems to work out so well for him. The episode is a brilliant look at Homer through someone else’s point of view. Watching Grimes go mad at Homer’s success is strangely hilarious as the show really embraces its dark humor in a big way.
4 Lemon Of Troy
One of the great things about The Simpsons is how they can adapt their outlandish humor to tell all kinds of entertaining stories. This episode is very much an adventure story, with the feel of the classic “behind enemy lines” war movies. After a gang of kids from Shelbyville steal Springfield’s lemon tree, Bart organizes a rescue mission to take it back.
The mission is surprisingly thrilling even when played for laughs. The dynamics of the group of spies is a lot of fun as are the strange similarities Shelbyville shares with Springfield. In the end, this is one of the Simpsons‘ most entertaining and fun-filled episodes.
3 Cape Feare
Sideshow Bob has proven to be one of The Simpsons best recurring characters. Voiced to perfection by Kelsey Grammer. Bob is a mad genius who has had multiple run-ins with Bart, but none more memorable than this thriller-esque episode. In a parody of Martin Scorsese’s Cape Fear remake, Bob is released from prison and sets out to get his revenge on Bart.
Though a Scorsese thriller might seem like a strange basis for The Simpsons, it proves to be the perfect set up for some great jokes. Who could forget the infamous “stepping on a rake” gag? It also manages to be an appropriately suspenseful episode even with the jokes.
2 You Only Move Twice (Season 8, Episode 2)
Hank Scorpio might just be the best single-episode character in the show’s history. When Homer gets a job in a new exciting job in a town called Cypress Creek in the mysterious Globex Corporation, Homer’s new boss, Hank Scorpio, proves to be friendly and enthusiastic. He is also a megalomaniac akin to a James Bond villain. Of course, Homer is oblivious to this fact.
The episode has a lot of fun moments with the family trying to fit in to their new too-perfect life in a new town. But the highlight of the episode is clearly Scorpio. He has so many strange and wonderful one-liners and his villainous activities which go on in the background are brilliant.
1 Marge Vs The Monorail
The people of Springfield could never be considered a bright group of citizens, and their stupidity often leads to some hilarious events. In this classic episode, the town is conned into buying a monorail from a shady traveling salesman. Marge’s suspicions begin to grow about the safety of the new purchase as Homer is named the monorail conductor.
Written by the great Conan O’Brien, the episode is packed with his outlandish humor. It features a glorious cameo from Leonard Nimoy. It has a classic Flintstones parody. It even has one of the show’s best musical numbers (based loosely on the musical, The Music Man). The episode is wall-to-wall great moments that we could watch again and again.
10 Time Travel Movies That Are Not Sci-Fi (According To IMDb)