11. Itchy and Scratchy Land
Simpsons traveling episodes are usually hit or miss, but when the family ventured to the Jurassic Park/Disneyland hybrid Itchy and Scratchy land, not even axe wielding robots could stop the hilarity. A clever, detailed satire on the Disney empire, “Itchy and Scratchy Land” is a rollercoaster ride into the heart of classic Simpsons.
10. Treehouse of Horror V
“Treehouse of Horror” episodes were a smart way to open up the season during the MLB playoffs. The short story format allowed the writers to concoct three distinctly creative horror tales, almost like a spring training before the real season began. The best of these collections is easily “Treehouse of Horror V.” Detailing Homer’s toasted, time-twisting journey and Bart and Lisa’s escape from a cannibalistic elementary school, the episode would have been great with these shorts alone. But the highlight is Homer going crazy with no beer or TV in the biting Kubrick parody “The Shinning,” this Halloween episode was elevated to new horror heights.
9. Homer’s Phobia
As The Simpsons evolved through later seasons, the writers became increasingly adept at tackling social and cultural topics. And John Waters take as a gay nostalgia shop owner in “Homer’s Phobia” was a hilarious skewering on homophobia and gay culture as Homer struggles with his fear that Bart may be gay. Homer’s personal journey to keep Bart walking down a straight path in the face of Hawaiian shirts and gay steel mills is a riotous event. “Homer’s Phobia” is the shining exemplar of the Simpsons social issue episodes, equally smart and funny for straight and LGBT audiences alike.
8. Who Shot Mr. Burns? (Part Two)
The “Who Shot Mr. Burns?” saga encapsulated the attention of TV audiences everywhere. Viewers desperately rewatched the first episode of this series to discover clues others may have overlooked. But the Part Two conclusion was more than just a solution to the murder mystery. It was an incredibly satisfying and hilarious episode in its own right, detailing Chief Wiggum’s detective incompetencies, Smithers’ poor choice in sitcoms, and a stunning vengeful musical number by Tito Puente. Just thinking about a bedridden Burns only being able to say Homer’s name is a laugh out loud moment.
7. Stark Raving Dad
There’s a stark difference between the first two seasons of The Simpsons and season three. The beginner seasons were crude and formulaic, while later seasons were zany and surreal. And that shift took place with season three’s opener “Stark Raving Dad.” After Homer gets to a mental hospital for wearing a pink shirt, he shares a cell with a large imposing bald man who claims to be Michael Jackson. What follows is a completely bizarre but undeniably hilarious story, establishing the tone and key elements that would define the show’s golden era.
6. Flaming Moe’s
As “ Stark Raving Dad” was the spark to the golden era, “Flaming Moe’s” was the torch. The story Homer’s cough syrup cocktail, Moe’s unjust theft and Ms. Krabappel’s seduction of Aerosmith band members got audiences drunk on laughs in Season 3. “Flaming Moe’s” announced loudly to the world that The Simpsons had arrived, and that no one had to pay a cover fee to get in on the fun. Let’s drink to that.
5. A Fish Called Selma
Phil Hartman’s guest voices were so beloved by fans that his characters often proved to be the best part of the episode despite their brief time on screen. So it was only natural that Springfield’s favorite D-list actor Troy McClure got his own episode in “A Fish Called Selma,” detailing McClure’s career, romantic, and aquatic woes. Featuring the infamous “Stop the Planet of the Apes, I Want to Get Off!” musical, this episode gave Hartman full creative vocal reign, and the end result is one of the Simpsons’ best.
4. Marge vs. the Monorail
Conan O’Brien is often credited with bringing the zany and surreal element to the show. And his best penned episode is “Marge vs. the Monorail,” a parody of “The Music Man” where the town falls victim to Lyle Lanley’s empty monorail scheme. Featuring arguably the most famous song from The Simpsons and a completely bizarre guest appearance by Leonard Nimoy, “Monorail” never derails and always accelerates forward with goofy jokes and gags.
3. 22 Short Films About Springfield
As the series evolved, writers realized that not all stories had to focus on the Simpsons clan. And “22 Short Films About Springfield” is an exemplar display of Springfield’s citizenry, detailing several original stories of recurring characters during a common day about town. An incredibly clever and innovative display of storytelling, “22 Short Films About Springfield” is some of the most diverse writing and humor on the show, a festival and ode to The Simpsons’ other beloved residents.
2. Cape Feare
Sideshow Bob episodes don’t air that often, so it’s always a welcome occasion when the pineapple haired criminal returns to town. Out of all of his visits, “Cape Feare” is miles ahead of its predecessors, with Bob trailing the Simpson family after being released from prison. “Cape Feare” is full of great moments, including Homer’s desires to become John Elway in the witness protection program and Bob’s full recital of the H.M.S. Pinafore. But the extended rake gag, with Bob stepping on garden rakes nearly a dozen times is a huge experiment that pays off big time, thwacking viewer’s heads with a full force of humor. The rake gag is “Cape Feare’s” secret ingredient, the beginning catalyst of one of the best episodes in Simpsons’ history.
1. Last Exit to Springfield
A dental plan. References to “Batman, The Godfather: Part II and Yellow Submarine. Homer holding a position he is by no means qualified for. Mr. Burns holding the town hostage with his immense wealth and power. A light but memorable original song. Fake vomit. And enough jokes and gags that shouldn’t be physically possible to tell in 22 minutes, “Last Exit to Springfield” is The Simpsons’ swan song, the culmination of masterful writing and voice acting that utilizes all the best elements of the show in full force. Never lacking in pace while always being funny and irreverent, “Last Exit to Springfield” simply is the greatest episode there ever was, and ever will be.