Like all cartoons, The Simpsons can get pretty weird sometimes. That’s the nature of the medium, which truly makes the art of storytelling feel like it has no boundaries. The creative freedom to make zany and absurd choices can truly make episodes sparkle, like when Homer falls asleep and has that hilarious dream on his drive home in “Lisa’s Pony”—or when he strolls through a wonderland of chocolate during a rather significant meeting with his bosses in “Burns Verkaufen der Kraftwerk.”
Of course, the show doesn’t have to feature surreal sequences to upend expectations. There are several ways that an entry of The Simpsons can be unconventional. Take structure, for instance: “Who Shot Mr. Burns? (Part One)” ends both the episode and the season on a cliffhanger, “Barthood” takes place before and after the timeframe of the normal Simpsons world, “22 Short Films About Springfield” features a bunch of short stories in the span of a normal-length episode, and “24 Minutes” embraces the linear but experimental style of the hit show 24. Then there’s every single “Treehouse of Horror” episode, which is inherently strange by splitting into three main stories that are considered non-canon. Combing through 36 seasons to find ten that are quirkier than the rest is no easy task—even to the point where it’s pretty subjective. Environment is another big factor, at which point “The Mysterious Voyage of Our Homer” may come to mind, but the following ten episodes get weird and stay that way. Showing that taking chances with tone, setting, style, and more can yield a variety of results, these Simpsons stories stand out from the crowd in more ways than one. (That doesn’t make them all good, though.)
10
“The Springfield Files”
Season 8, Episode 10 (1997)
The original Star Trek‘s Leonard Nimoy humorously and ominously introduces “The Springfield Files,” giving it the feel of a Treehouse of Horror special. Except it’s not; it’s an X-Files parody with enough references to other sci-fi and horror media to make your head spin. Strange occurrences include an old man turning into a Dr. Seuss-like creature and a famously illegal alien-crossover the show would probably have trouble repeating if they tried to do it again.
One of Season 8’s strongest episodes, this features a spooky score that helps set the unusually eerie tone throughout the entire story. That reference from The Shining playfully takes up so much space on the screen, and Nimoy leaving mid-episode is great. What makes this all the more bizarre is that he actually shows up in the tale he himself was just telling. With this alien plot taking up the whole episode, the texture of “The Springfield Files” makes it feel consistently and wonderfully eccentric.
9
“Treehouse of Horror VI”
Season 7, Episode 6 (1995)
The sixth “Simpsons Halloween Special” is the first one to forgo a formal introduction, choosing instead to briefly show a beheaded Krusty riding horseback for some reason. Anyway, “Attack of the 50 ft. Eye Sores” is the first segment, in which Homer takes a donut and prompts all the giant advertisements in town to come to life. Next, we have “Nightmare on Evergreen Terrace,” in which Groundskeeper Willie is attacking all the Springfield children in their dreams.
We certainly get a variety of creepy and strange settings there, but the third segment is when The Simpsons really pushes the boundaries. It’s called “Homer³,” where Mr. Simpson winds up in a mysterious zone that makes him enter the third dimension. He can hear his family, and vice versa, but he can’t get out. The segment sees various citizens of Springfield trying to get him out while he avoids further danger, and it’s absolutely bonkers to watch. Especially the end.
8
“Moe Goes From Rags to Riches”
Season 23, Episode 12 (2012)
There are several TV show parodies in the opening to “Moe Goes from Rags to Riches,” which is an interesting start to a perplexing episode. Everyone’s being meaner to Moe than usual, joking that his best friend is his bar rag. This might have viewers expecting a story about Moe trying to make a new friend in town, but this plot takes a hard left turn. A spotlight lands on his rag, and it comes to life. Telling the audience he wasn’t always like this, he takes us back to medieval France.
Thoughts like “What on Earth is happening?” and “Uh…okay” should be expected to pass through your head while watching this offbeat entry. The rag narrates through stories set in medieval times, Persia (ala A Thousand and One Nights), Spain, and elsewhere. We learn that the rag was woven with demon wool, helped Michelangelo paint the Sistine Chapel, and took part in other major historical events. The minor subplot notwithstanding, this episode is pretty nuts.
7
“Holidays of Future Passed”
Season 23, Episode 9 (2011)
There can’t be a “Weird Simpsons Episodes” list without one of the stories that takes place in a different time. Possibly the best of the future episodes, as well as one of the best holiday-themed Simpsons episodes, “Holidays of Future Passed” starts with Thanksgiving, travels through decades of Christmases, and winds up at a Christmas in which Bart has two kids and Lisa has a teenage daughter. “The Itchy and Scratchy Show” gets shown via hologram, Maggie’s a famous singer, kids can hear thoughts, and more.
In fact, there are too many details about this world to list more than a fraction of its unique qualities. But this entry is also weird on a behind-the-scenes level: it was originally intended as The Simpsons‘ series finale, as the team wasn’t sure that it would be renewed past the 23rd season. (How wrong they were.) With that in mind, fans can briefly entertain the alternative world where this surprisingly strong and consistently strange future episode marked the end of this animation giant.
6
“The Man Who Came to Be Dinner”
Season 26, Episode 10 (2015)
“The Man Who Came to be Dinner” starts with one of the more peculiar couch gags (involving an art gallery), but it’s the main plot that really makes this one stand out. The Star Wars crossover stuff at Dizzneeworld is amusingly meta, but things get much weirder very quickly when the family takes a ride that shoots them into outer space.
The beloved Kang and Kodos appear on a screen, at which point Homer complains that it’s not even Halloween (another funny meta moment). There’s a potato chip sequence reminiscent of Season 5’s “Deep Space Homer,” and Homer accidentally grows an extra hand out of Marge’s hair. When we arrive on the aliens’ planet, we might as well be in an episode of Futurama. Needless to say, it’s non-stop strangeness for the rest of the story—which is also funnier than expected for Season 26.
5
“Simpsorama”
Season 26, Episode 6 (2014)
While “The Man Who Came to Be Dinner” feels like a Futurama episode, “Simpsorama” literally is a crossover between Matt Groening‘s two beloved shows. The opening to this one sums up what we’re about to see: “A Show Out of Ideas Teams Up With a Show Out of Episodes.” Homer referring to himself in the third person is odd, but not nearly as much as what happens right after.
Bender (voiced by John DiMaggio) shows up in the Simpsons’ basement. Lisa and Bart commenting on the similarities between him and Homer is fun, and it gets more interesting when Futurama‘s other main characters appear. There’s some wild stuff going on in the future, and it’s all Bart’s fault. Maggie and Bender wind up alone in present-day Springfield while the others get sucked into the future. This may only be relatively funny, but it’s definitely one of the weirdest entries of both shows.
4
“The Serfsons”
Season 29, Episode 1 (2017)
Employing a Game of Thrones-esque theme for the couch gag, “The Serfsons” starts off Season 29 in a fantasy setting. Maggie sucks on a beak, Homer kisses a horse’s foot, and the local nursing home is just a bunch of people hung up in webs. It’s also pretty weird to have Marge’s mother show up in an episode, let alone feature as a fairly important character. She got bitten by an ice-walker, and Marge is determined to save her.
This story features a funny spin on the classic recurring bit of Bart calling Moe’s sentient goo, a pair of wings on Mr. Burns, a talking missionary-lion, a giant nose, and much more. Lisa can perform magic, which isn’t legal for serfs and results in her capture. Homer leads a crowd of angry peasants (and severely underused trees) to get her back, and it’s no surprise we have lots of references to famous fantasy media. Overall, this is one of the most unorthodox entries by a mile.
3
“Brick Like Me”
Season 25, Episode 20 (2014)
For The Simpsons‘ 550th episode, the team boldly animated the show in a LEGO-style. This entry forgoes the typical introduction for a cold open: Homer wakes up from a dream about co-branding. As he opens his eyes, we see Marge in LEGO form. It’s jarring, and it appears like things are going to stay this way, too. Actually, though, it doesn’t take very long for the episode to use a flashback as an excuse for their typical animation style.
Then LEGO-Homer starts seeing reflections of himself as the normal Homer, establishing the central conflict: an existential crisis about living in a fantasy world in which he can actually relate to his daughter. This episode also obviously has similarities with The Lego Movie—something the story alludes to in the end. With Homer trying to escape his perfect LEGO reality to return to his real one, “Brick Like Me” goes down as one of the most consistently odd entries yet.
2
“Treehouse of Horror XXXIII”
Season 34, Episode 6 (2022)
This famous “Treehouse of Horror” is out there even for “Treehouse” standards. It goes to show that 33 seasons in, The Simpsons can still surprise us. Instead of the typical trip to a graveyard, a hardcover book simply opens up to the first segment: “The Pookadook,” a mediocre parody of The Babadook. Things get much weirder with the second segment, as it’s all in the style of anime. Lisa kills a jailbird with the book she found on the street. She then goes on a “justice-spree” that includes many funny deaths.
The final segment is stranger still. It begins with a twist on Season 4’s famous “Monorail”-episode (one of Season 4’s best entries). In the middle of a scene, two intoxicated fans come along to say Homer’s line about a possum. Soon, an announcer says that this episode is malfunctioning, and Homer discovers that he’s not a man; he’s intellectual property. One of the most meta episodes of any show ever, it ends with an ominous shot of other areas designated by their own famous cartoons (and a brief yet unusual appearance by Kang and Kodos).
1
“The Simpsons’ 138th Episode Spectacular”
Season 7, Episode 10 (1995)
Choosing a random number to have a particularly special Simpsons entry, someone thought it would be fun to do “The Simpsons’ 138th Episode Spectacular.” What exactly should one expect from a title like that? The short answer: a lot. This is not your typical Simpsons clip show: it has unseen footage, outtakes, material you can’t view in syndication, and it even displays the origins of the beloved cartoon family. Can’t get more meta than that.
Hosted by Troy McClure, this wildly structured entry also includes fan letters and trivia questions with amusingly false answers—including how much Maggie costs in the opening sequence. Deleted footage is sourced from episodes including “Krusty Gets Kancelled,” “Mother Simpson,” and “Treehouse of Horror IV.” Along with all the nudity in the credits while KC and the Sunshine Band‘s “Shake Your Booty” plays, this episode takes the word “unconventional” and takes it to the next level. Hardcore Simpsons fans should enjoy this extraordinary oddity.