20 Iconic ‘The Simpsons’ Episodes that Celebrate Arts and Culture

The Simpsons is a cultural Icon. The show began in the 1980s as a mini-series on the Tracy Ulman Show and morphed into one of a generation’s longest-lasting and most recognizable pop culture hits.

The Simpsons has provided laughs for over 30 years and has a long history of featuring important works of art. The show has parodied paintings, sculptures, novels, poetry, classical music, and more, often in the same episode.

To showcase some of the brilliant parodies of pop culture performed by the hit show, here are 20 iconic episodes that feature famous works of art across all mediums.

*Note that the episodes are listed in the order currently available on Disney Plus. Some of these episodes appeared in different positions during the original run.

Season 1 Episode 11 “The Crepes of Wrath”

“The Crepes of Wrath” is the first episode of The Simpsons to showcase famous paintings. Bart gets in trouble at school, and rather than punish him, Principal Skinner and Homer decide to ship him away as a foreign exchange student.

Bart travels to France, and on the motorcycle ride to his accommodations, passes through a variety of influential artworks. He crosses over the bridge from Monet’s “Bridge Over a Pond of Water Lilies,” through Van Gogh’s “Wheatfield with Crows,” into Rousseau’s “Dream,” and disrupts Manet’s “Luncheon on the Grass” before he finally arrives at the dilapidated shed where he’s meant to spend the next three months.

S2 Episode 8 “Bart the Dare Devil”

The main story of “Bart the Dare Devil” features Bart attempting riskier and riskier skateboarding stunts after watching a Dare Devil, most likely based on the famous Evil Knievel, at a monster truck rally.

In a clever juxtaposition between classical art and modern entertainment, the beginning of the episode focuses on Lisa’s band recital. Here, the Springfield Elementary Orchestra plays impressive renditions of Franz Schubert’s “Unfinished Symphony” and Pyotr Ilyich Tchaikovsky’s “1812 Overture”.

Season 2, Episode 9 “Itchy Scratchy & Marge”

In “Itchy Scratchy & Marge,” baby Maggie gets influenced by the violent cartoon “Itchy & Scratchy” and attacks Homer. Marge reacts by protesting against the cartoon and ultimately wins the day with the show’s cancellation.

When Michelangelo’s “David” comes to the local art museum, the community mom group that was integral to Marge’s win wants to protest it as well, claiming the nudity present in the statue is just as dangerous to children as the violence present in “Itchy & Scratchy.” Marge disagrees and realizes that she was wrong to limit the freedom of artistic expression in any medium.

Season 2 Episode 17 “Old Money”

The main story of “Old Money” revolves around Grandpa Simpson. He inherits a large sum of money from his deceased girlfriend but doesn’t find any joy in spending it. He decides to give the money away but can’t find anyone in Springfield worthy of it.

As he takes a walk to clear his head, he is shown in the bar from the painting “Nighthawks,” sipping on coffee. His wanderings help him realize he doesn’t have enough money to truly help anyone, so he heads to the casino to make more. When Homer tries to prevent him from losing it all, Grandpa Simpson quotes lines from the famous poem by Rudyard Kipling “if”:

“If you can make one heap of all your winnings

 And risk it on one turn of pitch-and-toss,

And lose, and start again at your beginnings

And never breathe a word about your loss

Yours is the Earth and everything that’s in it,   

And—which is more—you’ll be a Man, my son!”

Season 5 Episode 2 “Cape Feare”

The title and plot of this episode are clear references to the 1991 thriller “Cape Fear.” Side Show Bob, who blames Bart for his imprisonment, sends threatening letters to Bart and then follows them to a houseboat, seeking vengeance.

The movie isn’t the only work of art referenced in this episode. Bob grants Bart a final wish, and the quick-thinking boy appeals to Bob’s musical talent and love of culture, asking him to perform the entirety of “HM Pinafore,” a comedic opera. Bob happily obliges, buying Bart much-needed time for the boat to arrive at the shore.

Season 5 Episode 5 “Treehouse of Horror IV”

Like most “Treehouse of Horror” episodes, number IV is an anthology of short stories. This episode features Bart as a narrator for the coming tales.

As Bart discusses the horrors to come in the story you’re about to see; he walks through an art gallery filled with parodies of some of the most famous paintings of all time. He walks by a portrait of Homer in the style of Van Gogh, Lisa recreating Munch’s “The Scream,” Bart replacing the “Son of Man,” and Maggie in a Surrealist nightmare as part of Dali’s “The Sleep,” among other paintings.

This episode also features the “Mona Lisa.” In the third story, a parody of “Bram Stoker’s Dracula,” police officers burn the painting, mistakenly believing that antiquities are the cause of the violence in Springfield.

Season 5, Episode 9 “The Last Temptation of Homer”

“The Last Temptation of Homer” introduces a new coworker to the nuclear powerplant, the gorgeous Mindy, who, as it turns out, has a lot in common with Homer. When Homer first meets Mindy, he daydreams of her depicted as the Venus in Sandro Botticelli’s “The Birth of Venus.” Lenny and Carl make up the cherubs surrounding Venus in Homer’s fantasy.

This episode also pays homage to the iconic movie “The Wizard of Oz,” as Monty Burns has a fleet of flying monkeys, which he sends to attack Homer and Mindy after finding out they paid for room service on the power plant’s dime. Unfortunately for Mr. Burns, the monkeys don’t work for him, and they immediately fall out of the sky.

Season 5 Episode 17 “Bart gets an Elephant”

Although the main story in Season 5, Episode 17, isn’t related to art, there’s an important scene near the beginning that features one of the most famous paintings of all time.

The Simpson family is stuck cleaning the house, and Bart lazily dusts everything in his path without paying attention. Unfortunately, “American Gothic,” the iconic image of a father and daughter in front of a farmhouse that became a symbol of American perseverance during the great depression, is one of the things in his path.

Bart scrubs the painting clean, revealing a note underneath signed by artist Grant Wood stating, “if you can read this, you scrubbed too hard.”

Season 6 Episode 18 “A Star is Burns”

“A Star is Burns” is a celebration of film and the film critic industry. The entire episode celebrates the art of filmmaking, but it also references one of the most iconic masterpieces in human creation. That masterpiece is, of course, Michelangelo’s “Creation of Adam,” the center panel of his epic portrayal of biblical images on the ceiling of the Sistine Chapel in Vatican City.

In this episode, Springfield hosts a film festival to raise money. Monty Burns, obsessed with winning, hires a professional team of directors and cinematographers to create an expensive and wildly inaccurate portrayal of his life. The opening credits of his film features a parody of the “Creation of Adam,” with Mr. Burns taking the place of Adam, reaching out to God.

Mr. Burns’ attempts at winning the festival were thwarted when the judges he didn’t bribe voted for Barny’s film about his struggles with alcoholism.

Season 6 Episode 2 “Lisa’s Rival”

Lisa’s Rival retells the famed Edgar Allen Poe poem, “The Tell-Tale Heart.” Although not the first Simpson’s episode to retell this story (that honor goes to Season one’s “a Tell-Tale Head”), this one has a more direct reference to the tale in the form of a diorama.

In this episode, Lisa meets Allison, a bright student, talented saxophone player, and one year younger than Lisa. It seems to Lisa that Allison is better than her at everything that makes Lisa unique.

The episode culminates with a diorama contest. Allison portrays “The Tell-Tale Heart” with a moving floor piece and metronome to symbolize the sound of the beating heart. In an attempt to sabotage Allison, Lisa swaps the diorama with a bloody cow heart.

Overcome with guilt over what she’s done, she screams, “It’s the beating of the hideous heart!” and recovers the original diorama. Both girls lose to Ralph, whose project only contained Star Wars action figures.

Season 6 Episode 20 “Two Dozen and One Greyhounds”

“Two Dozen and One Greyhounds” is an episode that revolves around the Simpson’s family dog, Santa’s Little Helper. Santa’s Little Helper feels lonely and finds love with a lady greyhound named She’s the Fastest.

The two dogs have an epic romance, recreating the famed meatball scene from “Lady and the Tramp” and having their picture taken in a cut out of Cassius Marcellus Coolidge’s iconic painting “Dogs Playing Poker.”

As the episode name suggests, the main story is a parody of the Disney classic “101 Dalmatians”. Santa’s Little Helper and She’s the Fastest have a litter of puppies, which Monty Burns promptly steals. He has a nefarious plan to make a tuxedo out of the puppy’s fur. Burns is thwarted by Bart and Lisa but wins the day by raising the puppies to be champion racers.

Season 6 Episode 6 “Treehouse of Horror 5”

The Simpsons “Treehouse of Horror” episodes are Halloween specials that often retell infamous scary stories in iconic Simpsons fashion. These specials have parodied macabre tales such as “The Raven,” Slasher films such as “Nightmare on Elm Street,” and science fiction novels, like “The Island of Dr. Moreau.”

However, season six’s “Treehouse of Horror” special features one of the best horror parodies as it takes on Stanley Kubrick’s rendition of “The Shining.” The episode finds the Simpson family traveling to an old, abandoned hotel to be its off-season caretakers.

The parody abounds with imagery from the original film, including the words “redrum,” which Maggie creates with her reading blocks, breaking open a door with an ax by the phrase “Here’s Johnny!” and the blood getting off the elevator, wherein Monty quips “that’s odd, usually the blood gets off at the second floor.”

The Simpsons use the lack of television to drive Homer to his murderous ways, replacing the famed “all work and no play makes Jack a dull boy” with “no tv, no beer makes Homer go crazy.” The entire story is a clever nod to the original movie and a fantastic parody of a horror classic.

Season 6 Episode 9 “Homer Badman”

Although not the first time the iconic sculpture “Venus de Milo” appeared in The Simpsons (It also appeared in season 4 as an ice sculpture, and season 5 in Monty’ Burns’ collection!), this episode is perhaps its most iconic appearance.

In “Homer Badman,” Marge and Homer score tickets to a highly anticipated candy convention. The star of the show is the Gummy de Milo, a gummy candy sculpted in the shape of “Venus de Milo.” Homer steals the gummy and then loses it in his escape, only to find it again stuck to the babysitter’s pants.

When he pulls the candy from her pants, she mistakenly believes he was groping her and rallies her feminist group to protest against him. Homer is cleared when Grounds Keeper Willie produces a film proving that Homer was indeed going after the Gummy De Milo.

Season 6 Episode 22 “Round Springfield”

As Lisa is a serious jazzophile, it makes sense that The Simpsons would celebrate the art of jazz. Although not the first episode to feature this music as an art form, it’s perhaps the most memorable and iconic.

Bart gets sick in “Round Springfield” after ingesting a jagged metal Krusty-O. While at the hospital, Lisa reconnects with her hero, Bleeding Gums Murphy, whose character is loosely based on the famous saxophonist Sonny Rollins. Murphy tells Lisa his history, a sad tale of success and losing it all, culminating in him ending alone in the hospital.

The two jam together, creating a rendition of Carol King’s famous “Jazz Man.” Lisa goes on to have an epic performance at her school recital, only to find that Murphy has passed away while she was gone. She then commits to honoring Bleeding Gums, finding his one album, and playing it for all of Springfield to hear.

The episode also features a quick homage to “Star Wars” and the “Lion King,” with Darth Vader and Mufasa appearing in the clouds as Lisa tries to say goodbye to Murphy.

Season 7 Episode 16 “Lisa the Iconoclast”

In “Lisa the Iconoclast,” the town of Springfield is getting ready to celebrate its bicentennial. In preparation for the festival, Lisa’s teacher instructs the class to write an essay about Jedediah Springfield, the town’s hero and founder.

Lisa heads to the historical center to research for her assignment, only to find proof that the town’s hero was actually a fraud!

The episode revolves heavily around a portrait of George Washington, based on the painting by Gilbert Stuart. The artwork is displayed in both Lisa’s elementary classroom and the cultural center, but the bottom portion is incomplete in both instances. Lisa discovers that the note proving Jedediah is fraud was written on paper torn off of the original painting.

Season 7 Episode 22 “Raging Abe Simpson and His Grumbling Grandson in” ‘The Curse of the Flying Hellfish’”

“The Curse of the Flying Hellfish” revolves around a treasure trove of paintings stolen from Germany in World War II. Grandpa Simpson and Monty Burns are the sole survivors of the WWII squadron who stole the works. Knowing that they couldn’t profit off the paintings right away, the squadron made a pact that the last man standing could have all the paintings, assuming that the heat would be off the stolen artifacts by that time.

Mr. Burns decides he wants the paintings now and attempts to kill Grandpa Simpson to get them. In the end, Grandpa Simpson finds the artifacts, but the State Department rushes in and returns them to the descendent of the original owner.

Many of the paintings featured in the episode were genuinely lost in the war. They include “Portrait of a Young Man” by Raphael and “Madonna and Child” by Botticelli.

Season 9 Episode 15 “Das Bus”

The fifteenth episode of The Simpsons’ ninth season is a spectacular parody of the influential novel “Lord of the Flies.” The school bus crashes while en route to a Model UN Club field trip, leaving the children stranded on a deserted island.

Although the children envision a paradise similar to the “Swiss Family Robinson,” the reality is much harsher. They lack food and shelter and quickly turn on each other. Milhouse is accused of eating all of the food, and the children want to kill him for it.

Lisa acts as the voice of reason, allowing a trial, but the kids don’t like the verdict and try to stone Millhouse to death. Lisa and Bart try to defend him, finding themselves on the wrong side of the group’s rage. They hunt Bart, Lisa, and Milhouse across the island, only to discover that a wild boar was responsible for eating the food.

This episode also features a story about the new (at the time!) cultural phenomenon, the internet. Homer realizes that people can make money online, so he sets up an internet business without even having a computer. Homer’s ads draw the attention of Microsoft frontman Bill Gates, and his company ends up being destroyed.

Season 9, Episode 17 “Lisa The Simpson”

In “Lisa The Simpson,” Lisa is appalled to discover the Simpsons Gene, a genetic disadvantage that appears to make Simpsons dumb. Many members of the Simpsons family get stupider and stupider as they age, and Lisa worries that she’s losing the intelligence that makes her special.

Lisa heads out to Springfield’s important cultural hubs to give her brain one last treat before it, as she describes it, melts into a Simpson’s Sludge. She visits an art gallery and admires “Painting” by Joan Miro, explaining the intricacies of light and shadow present in the painting to the gallery attendant, who claims he painted it and put the real version in his garage.

Season 10 Episode 19 “Mom and Dad Pop Art”

“Mom and Dad Pop Art” is an entertaining look at the modern art movement. Although often critiquing modern art, it also celebrates it and features many iconic works from various art movements.

The episode depicts Homer trying to build a BBQ fire pit. He fails miserably, and in a fit of rage, destroys the grill in spectacular fashion. As he attempts to dispose of the monstrosity, it hits the car of an art gallery owner, who wants to display the piece in her gallery as an expression of raw human emotion.

Although Homer’s first piece is a hit, his following pieces fall flat, as the art world constantly looks for something new. Homer and Marge head to the Springsonian museum for inspiration, where numerous works by famous artists are parodied, including Picasso, Oldenburg, Warhol, and Rothko.

Mom and Dad Pop Art features a plethora of art world references. Barney draws a version of “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat to attempt to pay his bar tab, while the “Vitruvian Man” and Andy Warhol appear in Homer’s dream. Famed pop artist Jasper Johns even makes a cameo.

Season 10 Episode 22 “They Saved Lisa’s Brain”

In “They Saved Lisa’s Brain,” Lisa becomes frustrated by the lack of culture in Springfield. Her family drags her to a gross-out competition that culminates in the destruction of a Van Gogh exhibit van. The works destroyed include “A Starry Night,” “Self Portrait with Felt Hat,” “Pair of Rubber Boots,” and “Still Life of Open Bible.”

The rest of the episode involves Springfield’s Mensa chapter taking over governance of the city. This influx of power corrupts the Mensa members, and they all attempt to enact horrendous laws.

They are ultimately stopped when Stephen Hawking appears and criticizes them for their corruption.

The Simpsons continue to be a Cultural Icon

Though these twenty episodes only showcase the first ten seasons of the show’s run, The Simpsons continue to produce amazing episodes with commentary on art and pop culture. How many artistic and cultural references can you find in the next twenty seasons of The Simpsons?

Michael Dinich: Michael Dinich is a personal finance expert, podcaster, YouTuber, and journalist. Michael is the founder of Wealth of Geeks, a rapidly growing personal finance and pop culture website.
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