The episode expertly manages to tell an emotional story while also delivering laughs. Marge's reaction to Bart losing some of his innocence is heartbreaking. However, Homer's rant against Bart is also comedic gold, with him yelling, "Why do you think I took you to all those "Police Academy" movies, for fun? Well, I didn't hear anybody laughing." There is also one of the best one-off characters in the series with the grizzled mall cop Don Brodka.

14 22 Short Films About Springfield

Season 7, Episode 21

While the series started out as a comedic look at the titular dysfunctional family, The Simpsons has become as much about Springfield as a whole and the many wacky characters who live there. The ensemble is far too large to ever give them all their time to shine in one episode, but "22 Short Films About Springfield" is likely the best attempt at achieving just that. The title explains it all quite well as the episode simply features various stories from various Springfield characters with loose connections between them.

Along with featuring a lot of references to the similarly plotted Pulp Fiction, "22 Short Film About Springfield" is a fast-paced and hilarious ride through the mayhem of the town. Some of the highlights include Apu attempting to fit an entire day's worth of fun into his short work break, a glimpse at Bumblebee Man's home life, and Moe getting robbed. However, the highlight of the episode is Principal Skinner's attempt to treat Superintendent Chalmers to lunch which leads to the iconic "steamed ham" joke.

13 Deep Space Homer

Season 5, Episode 15

There are not too many shows that could take their earth-bound story into space and not feel ridiculous. In the case of The Simpsons, this seemingly farfetched premise makes for one of the best episodes of the series. "Deep Space Homer" finds NASA looking to increase interest in their space program by selecting an "everyman" to be the latest astronaut. Of course, Homer is chosen as the perfect candidate (along with Barney) and the hijinks ensue.

Homer Simpson is the kind of television character who can be transplanted into any situation and it will be entertaining to see what he makes of it. From the space training to the actual outer space adventure, "Deep Space Homer" gives Homer a lot of great moments. There are many references to 2001: A Space Odyssey, but one of the most iconic moments comes with Homer's zero-gravity snack.

12 Who Shot Mr. Burns?

Season 6, Episode 25

While fans might still debate how successful the reveal of the central mystery was, that doesn't distract from the fact that "Who Shot Mr. Burns" is a hilarious episode from beginning to end. One of the biggest reasons for this is that it puts Mr. Burns, one of the show's funniest and most outlandish characters front and center while allowing him to fully embrace his villainy. The episode sees Burns make plenty of enemies when he becomes a local oil baron and causes even more mayhem when he decides to block out the sun.

When Burns is shot, there are more than a few suspects to choose from. The saga is technically two separate episodes and the first part served as a season finale, leaving fans with the enticing cliffhanger. However, they can now be viewed as one hilarious, bold, and exciting episode that shows The Simpsons trying something different in its storytelling.

11 Homer At Bat

Season 3, Episode 17

The Simpsons having some fun in the world of sports has helped deliver some of the most memorable episodes and "Homer at Bat" embraces the concept more than any other episode. "Homer at Bat" takes liberally from different classic baseball movies as it follows Homer leading the Nuclear Power Plant baseball team in a winning season. However, with Mr. Burns wanting to ensure victory, he decides to replace most of the employee players with major league players.

The guest list is a star-studded affair of baseball legends, including Roger Clemens, Wade Boggs, Ken Griffey Jr., Jose Canseco, and Darryl Strawberry. The athletes make for hilarious additions to the show and score some huge laughs. The funniest aspects include the series of misfortunes that befall the players that take them out of the game, including Boggs getting in a bar fight with Barney and Griffey Jr. becoming addicted to Burns' nerve tonic. However, the best ongoing joke is Burns insisting Don Mattingly shave his sideburns while clearly not understanding what sideburns are.

10 Behind The Laughter

Season 11, Episode 22

While there is no sign of The Simpsons coming to an end anytime soon, "Behind the Laughter" is a rare episode in the long-running series that felt like it could have been a fitting finale. The episode switches up the format in a drastic way, revealing the life of The Simpsons is staged, with Homer, Marge, and their kids playing off a script. The mockumentary offers a behind-the-scenes look at the making of the show, the family's success, and the way they were all torn apart by fame.

The episode has a lot of fun commenting on the legacy of The Simpsons and poking fun at itself. The overly serious narration provides big laughs throughout with a deadpan delivery of some ridiculous lines. It is a bold direction to take the show in that doesn't work for all fans, but it shows the characters and the humor of the series can work outside of the typical format.

9 Treehouse Of Horror V

Season 6, Episode 6

The Treehouse of Horror episodes have become an annual favorite among fans so it makes sense that the best installment of these Halloween-themed episodes turns out to be one of the best Simpsons episodes of all time. "Treehouse of Horror V" follows the established format of these specials, offering three horror stories — a parody of The Shining, a story of Homer's time travel antics changing his reality, and a gruesome tale of Lisa and Bart's teachers beginning to eat the misbehaving students.

The Shining parody is often regarded as the best segment in all of the Treehouse of Horror's long history and it is hard to argue with that. Seeing Homer unleashing his own unhinged take on Jack Nicholson is a delight as is the recreation of the movie's iconic moments. The time travel episode is filled with quick and hilarious jokes while the final segment shows how violent these Halloween episodes can be.

8 Homer The Great

Season 6, Episode 12

The town of Springfield holds a lot of unexpected secrets that often pop up never to be referred to again. Such is the case in "Homer the Great" in which Homer discovers his friends, and most of the male population of Springfield, are involved in a secret organization known as the Stonecutters. While Homer struggles to get into the organization and then is quickly dismissed, things change when he is revealed to be their prophesized leader.

This episode is a great example of the absurdity that The Simpsons can lean into without ever breaking the reality of the show. The idea of this powerful and ancient society that has secretly controlled what world operating out of Springfield is just something to accept and enjoy the ride. The episode features a terrific guest role from Patrick Stewart as well as one of The Simpsons' catchiest songs with the Stonecutters' own tune.

7 Bart Sells His Soul

Season 7, Episode 4

While Bart Simpsons has done many shameless things over the course of the series, "Bart Sells His Soul" is a great episode that shows the layers of his character. The episode sees Bart sell his soul to Milhouse for cash, deciding that a soul is a meaningless thing. However, he soon finds his life unraveling and begins to see the importance of holding onto such a key part of himself.

It is not often that the audience is in a position to feel sorry for Bart as he is usually doing whatever destructive thing that he wants. However, this is a special episode that shows the human side of the little troublemaker. It also never loses touch of the humor as Bart's increasing paranoia provides big laughs, as does a subplot in which Moe attempts to rebrand his bar as a family-friendly establishment.

6 Cape Feare

Season 5, Episode 2

Sideshow Bob is one of the most beloved recurring characters on The Simpsons, but "Cape Feare" really highlights what makes him so special. The episode finds Bob being released from prison and setting out on his mission to get revenge on Bart. In order to keep the boy safe, the Simpson family enters the witness protection and moves to a new home with Sideshow Bob in determined pursuit.

The episode is a detailed parody of Martin Scorsese's remake of Cape Fear, which is a funny movie to choose to poke fun at. However, it sets up the perfect episode to highlight the beloved Simpsons villain and is even responsible for the famous Sideshow Bob rake gag. Kelsey Grammer continues to bring the character to life with such energy and ion, making him a true menace who can also be made to look like a pathetic fool.