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20 Most Iconic Episodes of 'The Simpsons'


The Simpsons has more than 20 seasons under their belt. (If it's Homer's belt, those seasons are fit to burst.) But choosing the 20 best episodes of The Simpsons is very difficult since there are far more than 20 that are just wonderful. Some I love because I laugh so hard, and some I love because they touch my heart. I also tried to pick episodes that focused on a variety of characters, though most of them are about Homer Simpson. Finally, ranking my picks from best to worst is pointless, as one episode isn't really any better than the other.

So, in alphabetical order, here are my favorite 20 episodes of The Simpsons.

"Bart the Daredevil"

Twentieth Century Fox
In "Bart the Daredevil," Bart embarks on a life of death-defying feats when he sees a daredevil perform at a Monster Truck Rally. This episode makes my list mainly because of Homer's long, painful fall down the cliff... twice. "Bart the Daredevil," like other early episodes, isn't as much about Homer being a doofus, as a father whose trying his best, fails, and then redeems himself.

"Burns Verkaufen der Kraftwerk"

Mr. Burns
Twentieth Century Fox
In "Burns Verkaufen der Kraftwerk" (translated means "Burns Selling That Power Station") Mr. Burns sells the Springfield Nuclear Power Plant to a group of Germans. While I enjoyed the humor of Homer and the other workers either sucking up to or alienating their new German bosses, the best part of the episode has nothing to do with corporate takeovers or job loss: Homer in the Land of Chocolate. Homer imagines a Land of Chocolate, in which he prances through, eating even a passing dog. He gets excited about a 50% off sale, when the chocolate is all free. Who wouldn't love the Land of Chocolate?

"Cape Feare"

Cape Feare - The Simpsons
In "Cape Feare," Sideshow Bob is at his devious best. The Simpson family enters the FBI's Witness Relocation Program to escape Sideshow Bob when he is paroled from prison. But Sideshow Bob, determined to get to Bart, follows them, which leads to a final showdown on a houseboat. Bart is only saved when his last request before dying is to hear Sideshow Bob sing the entire score to H.M.S. Pinafore. Sideshow Bob replies, with his usual wit, "Very well, Bart. I shall send you to heaven before I send you to hell." Who else but Kelsey Grammer could play Sideshow Bob, with his rich baritone and elegant elocution?


Homer Simpson
Twentieth Century Fox

I can't think of another primetime comedy that appeals to all ages where alcoholism is the punchline. In "Duffless," Marge asks Homer to give up beer (not "deer," beer) for a month after he's arrested while driving drunk. We see Homer attending AA-like meetings (Ned Flanders drank schnapps!) and riding Lisa's bike when his driver's license is revoked. The subplot involving Lisa using Bart as a hamster substitute in her science experiment brings home the rivalry between syblings. This is a well-rounded, hysterical episode, ending with Homer choosing Marge over beer.

"A Fish Called Selma"

A Fish Called Selma - The Simpsons

"A Fish Called Selma" showcases the considerable talent of Phil Hartman as Troy McClure. Troy McClure's agent (Jeff Goldblum) encourages Troy to be seen in public with a woman in order to boost his career. (There are rumors he does strange things with fish!) Troy starts dating Selma, and it pays off. Eventually they marry, but Selma, who really is in love, realizes that it isn't working. But during Troy's comeback, one of the best musical scenes of all Simpsons episodes has McClure starring in Stop the Planet of the Apes, I Want to Get Off! Sing with me, "I hate every ape I see, From chimpan-a to chimpan-zee."

"Homer Alone"

Maggie Simpson
Twentieth Century Fox
Marge freaks out from the stress of taking care of her family, and sends herself to Rancho Relaxo. Lisa and Bart stay with Selma and Patty, and Homer is left with Maggie. I can relate to Marge's breakdown. I, too, fantasize about ordering alcohol and a hot fudge sundae from room service while I'm relishing a bubbly bath. I also belly laugh at Bart giving his aunt a bunion rubdown. Yecch. But the scene I enjoy the most is after Maggie has crawled away from home, and Homer can't find her. He phones the missing children hotline. When he's put on hold he hears Player singing, "Baby Come Back." Hysterical!

"Homer: Bad Man"

Groundskeeper Willie
Twentieth Century Fox
"Homer: Bad Man" originally aired in 1994, and sexual harassment was a hot issue in America. Only on The Simpsons could we watch an episode that begins at a candy convention and ends with Homer narrowly proving his innocence in allegedly sexually harassing his babysitter by showing a video made by a Scot named Groundskeeper Willie. (Homer only wanted to grab the rare Gummi Venus de Milo, which was stuck to her behind.) The end of "Homer Bad Man" provides great opportunities for trivia and the pause button: TV magazine Rock Bottom fast-scrolling list of corrections.

"Homer the Great"

Homer the Great - The Simpsons
"Homer the Great" is ridiculous, with one of the cartoon's all-time best songs and a wonderful guest star. Homer is inducted into the Stonecutters, a secret and exclusive group who have powerful means and influence. My favorite scenes: The Stonecutters song (We do! We do!); the sly joke about Number One referring to the leader, who is played by Patrick Stewart, a.k.a. Captain Picard from Star Trek: Next Generation, (stay with me) who referred to his second in command as Number One; the birthmark that declares Homer is the Chosen One; and the secret tunnel that allows Homer to zoom to work, bypassing a huge traffic jam.

"Hurricane Neddy"

Ned Flanders
Twentieth Century Fox
In "Hurricane Neddy," Ned Flanders' home is the only one destroyed by a hurricane. It shakes his faith in God and sends him to the psych. ward. I love the crazy, dilapidated home Springfieldians put together for Ned, including the hallway that gets narrower and shorter, like something out of Alice in Wonderland. I also love seeing Ned go off his rocker, giving his neighbors a piece of his mind. It's one of the only times we've seen him crack. The best scene, though, is the flashback to his childhood, where we get to see his beatnik parents.

"The Itchy and Scratchy and Poochie Show"

The Itchy & Scratchy & Poochie Show
Another favorite episode of mine from the eighth season is "The Itchy and Scratchy and Poochie Show." In this episode, Homer is hired as the voice of a new character on the "Itchy and Scratchy Show" named Poochie. Though Homer, and his writers, try to make the character cool and hip, Poochie is rejected. The entire story, though, is also played out as a new character, Roy, moves into the Simpson house. As Poochie is canceled and leaves Itchy and Scratchy to visit another planet, Roy leaves the Simpsons. The entire episode is a tongue-in-cheek take on the business of making cartoons.
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