My Top 10 Episodes of The Simpsons

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The All-American Family

The Simpsons is my generation’s defining cultural touchstone. It’s been on the air for 24 years now, making it the longest running network sitcom in television history. Its unparalleled mix of slapstick and sharp satirical wit have made the show untouchable. It’s almost impossible to have a conversation with a guy between the ages of 25 and 40 without a Simpsons reference popping up. The most moving sign of the show’s influence is that, when the editors of the New York Times took on the task of writing obituaries for every person who died on 9/11, they found that most of the men in that age group they profiled “were described as admirers of the show,” so much so that they stopped mentioning this fact in the obits.

So, when my friend and fellow blogsmith Juan Alvarado Valdivia and I challenged each other to write our Top 10 Episodes of The Simpsons, I knew it would be tough. I didn’t know that it would turn into the single most difficult post in the history of the blog. There are so many classic episodes with lines of dialogue that have become part of our national consciousness. And I say this as someone who thinks the show fell off precipitously and hasn’t really watched it in years (my list has no episodes later than Season 8).

So, while I fully expect to be pilloried for my choices here, just know that this is a task that is objectively impossible and a task on which it is impossible to be objective. So this is the countdown of my favorites. If you hate it and think I’m an idiot, then write your own goddamn list. Deep breath. Here goes nothing.

Honorable Mention: Treehouse of Horror IV

I disqualified the Treehouse of Horror episodes from consideration for the broader list. I think that they are, in fact, some of the funniest episodes in the history of the show, but because they’re typically divided into smaller skits, and the substance is so different from the regular episodes, I consider them separately. Still, I want to take the time to mention my favorite Halloween episode, Treehouse of Horror IV, which features perhaps the funniest 10-minutes in Simpsons history, “The Devil and Homer Simpson,” in which Homer sells his soul to the devil for a doughnut. The Devil, Ned Flanders (of course), furnishes him with the doughnut, and when Homer finishes it (of course) he ends up in hell (the Ironic Punishment Division joke–“Have all the doughnuts in the world!”–is fantastic), only to be released when Marge shows the “Jury of the Damned” that she already has the deed to Homer’s soul. This sequence narrowly beats out Treehouse of Horror V, which features a sublime parody of The Shining.

10. Bart vs. Australia

Mention this Season 6 episode to any Australian and he’ll admit, with a wry smile and a shake of the head, that “Yeah, they really got us.” It’s an episode full of totally loony jokes, with the best perhaps coming in the pub scene: “I see you’ve played knifey/spooney before,” and “Cof-fee? Be-er.” There’s also Bart mooning the entire country of Australia with “Don’t Tread on Me” written on his ass, and of course there’s the ending with the invasive species: Bart’s frogs, and the vengeful koala perched to the landing gear of the Simpsons’ escaping helicopter. This one is definitely an all-timer.

9. I Love Lisa

It’s a testament to The Simpsons that Season 4’s I Love Lisa checks in this low. It starts on Valentine’s Day, when Lisa, out of pity, gives friendless Ralph Wiggum an “I Choo-choo-choose you” valentine card. Ralph develops a crush on Lisa, and takes her to the live Krusty the Clown 29th Anniversary Special, on which Lisa tells Ralph (and the television audience) that she never liked him. The scene where Bart pinpoints the exact moment of Ralph’s heart tearing in half is one of my all-time favorites. Ralph, of course, goes on to give a moving performance as George Washington across from Lisa’s Martha in the school play, winning an apology and an offer of friendship from her. I’ve often said that if I could choose one Simpsons character to give a spinoff show to, it would be Ralph Wiggum. He’s the best.

8. A Streetcar Named Marge

I’m a book and film nerd, of course, and I’ve always loved Tennessee Williams’s A Streetcar Named Desire. The Simpsons version, in which Marge plays Blanche DuBois, drawing her inspiration from Homer’s boorishness, opposite a surprisingly ripped Flanders’s Stanley, is fantastic, especially the New Orleans song (sadly, audio only). As much as I love the Streetcar element of this Season 4 episode, I think the best part of it is the subplot in which Maggie is housed at (and starts a rebellion against) the brilliantly conceived Ayn Rand School for Tots.

7. Kamp Krusty

“We want Krusty! We want Krusty! We want Krusty!” Bart and Lisa being sent to the gulag-like Kamp Krusty, and the resulting improvement in Marge and Homer’s lives (Homer loses weight and grows his hair back), is funny. Lisa’s letters home are hilarious. Bart’s eventual revolt and Homer’s reaction “Don’t be the boy, don’t be the boy … D’oh!” are side-splitting. And Krusty’s arrival brings a couple of my all-time favorite Simpsons lines: “I’m sorry! They drove a dump truck full of money up to my house!” and “I’m going to take you kids to the happiest place in the world: Tijuana!” And the Tijuana sequence, told in polaroid photos, is fantastic. This Season 4 episode (that’s three in a row–goddamn Season 4 is great) just builds and builds and never stops getting funnier the whole time.

6. Lisa the Vegetarian

I don’t even know where to start: “You don’t make friends with salad, you don’t make friends with salad”? “Sure, Lisa, a wonderful, magical animal” that produces bacon, ham, and pork chops? Lisa stealing the pig from Homer’s BBQ and almost inadvertently causing Mr. Burns to give a million dollars to an orphanage? The best Troy McClure educational video ever, “Meat and You: Partners in Freedom”? The Paul and Linda McCartney (!) cameo? This Season 7 episode has it all.

5. Marge vs. the Monorail

Many of my friends cite this Season 4 masterpiece as their favorite, and it’s hard to argue. Written by Conan O’Brien, it features the classic monorail sales pitch, in song, of Lyle Lanley (voiced by the inimitable Phil Hartman), and of course Homer’s ascension to the position of conductor of the poorly constructed train. One of my favorite random lines in the show’s history is when Marge finds the family of possums nesting in the monorail control booth, and Homer responds: “I call the big one ‘Bitey.’ ” And the Leonard Nimoy cameo is priceless. It’s got a great argument for best episode, but there are a few that are just a bit closer to my heart.

4. The War of the Simpsons

Coming from Season 2, this is the oldest episode on my list, and it’s home to a number of instantly recognizable scenes: There’s the famous dinner party scene, in which Homer imagines that he was a witty and urbane host, but was actually a drunken fool who offends Dr. Hibbert and gets caught drooling at Maud Flanders’s cleavage. Marge signs them up for a marriage counseling retreat, which takes place next to a lake that’s home to the legendary giant catfish General Sherman. Marge makes Homer promise he won’t go fishing, a promise he of course breaks. He catches General Sherman, reeling in his foe after an epic Old Man and the Sea-esque battle, only to return to the dock to find a furious Marge waiting for him. To prove his love, Homer throws General Sherman back. The whole episode is classic, but my favorite part is the last scene, in which the bait shop cashier describes the man who came closest to catching General Sherman: “Went by the name of Homer. Seven feet tall he was, with arms like tree trunks. His eyes were like steel: cold, hard. Had a shock of hair, red, like the fires of Hell.” Honestly, this episode should be probably be higher on the list.

3. Homer at the Bat

I’ve been a huge baseball fan since I was around eight years old, and this Season 3 episode, which came out when I was ten, was square in my wheelhouse. The parody of The Natural, in which Homer makes his own bat, “Wonderbat,” from a tree struck by lightning, is hysterical. And the ringers that Mr. Burns brings in, Major Leaguers Roger Clemens, Mike Scioscia, Don Mattingly, Steve Sax, Ozzie Smith, Wade Boggs, Jose Canseco, Ken Griffey, Jr., and Darryl Strawberry, are all voiced by the actual players. This was an incredible feat for an animated series in its third season. The players all end up befalling hilarious accidents that prevent them from playing in the big game (my favorites are Scioscia getting acute radiation poisoning from working in the Nuclear Plant, and Burns throwing Mattingly off the team for his sideburns–amazingly, this came before Mattingly had his famous row with George Steinbrenner over the length of his hair), except for Strawberry, who plays Homer’s position. Strawberry hits nine homeruns, but Burns pinch hits Homer for him with the bases loaded in the bottom of the ninth to get the platoon advantage (“It’s called playing the percentages”), and Homer becomes the hero when he is hit in the head by a pitch, knocking him unconscious and driving in the winning run. This episode is perfect.

2. Homer’s Barbershop Quartet

Probably the only thing I’m a bigger geek for than baseball is music, as one look at this blog’s archive will tell you. To be more specific, I’m a geek about rock music, and most particularly the Beatles. I’ve read the Beatles Anthology book cover to cover, and watched the Anthology TV special. So this Season 5 episode, a parody of Beatlemania, hits me right where it hurts. It’s rife with inside jokes, from Homer’s “Thank you, and I hope we passed the audition” line, to the Meet the Be Sharps album cover (by the way, the name of their band is a great pun–the note B# is almost nonexistent, appearing only in the key of C# Major), to Chief Wiggum getting Pete Best-ed, to Barney’s “Number 8,” to the final scene, when the Be Sharps perform on the rooftop of Moe’s Tavern. The episode also features the show’s first Beatle cameo, George Harrison, who says dismissively of the rooftop performance: “It’s been done.”

1. El Viaje Misterioso de Nuestro Jomer

I’m sure this will be a controversial choice for the top slot, but this Season 8 episode has been my favorite from the moment I first saw it. So many classic goofy lines: Lenny, on Homer’s chili spoon: “They say he carved it himself, from a bigger spoon”; Flanders and his son, when his chili is revealed to be less than 5-alarm: “Are you going to jail? … We’ll see, son, we’ll see.” And of course, Chief Wiggum’s monologue about the “Merciless peppers of Quetzalacatenango, grown deep in the jungle primeval by the inmates of a Guatemalan insane asylum.” I love Homer’s psychedelic vision quest, with his spirit guide a coyote voiced by Johnny Cash. And the end, with the people of Springfield flocking to the beach to revel in the hot pants lost in the wreck of a cargo ship, is a perfectly Simpsonian non sequitir ending.

So there, you have it: My Top 10 episodes of The Simpsons. Feel free to commence with the insults and abuse. And go check out Juan’s list.

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3 Responses to My Top 10 Episodes of The Simpsons

  1. Pingback: My Top 10 Led Zeppelin Songs | From a Brooklyn Basement

  2. Pingback: The Top 5 Versions of The Weight on YouTube | From a Brooklyn Basement

  3. Enal Kreeny says:

    Controversial? It’s a tough one, but if someone put a gun to my head and demanded an answer, I would agree with your #1 choice. Fantastic episode.


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