This Sunday on Fox, The Simpsons will air its 500TH EPISODE. To put that number in perspective, that’s nearly 100 more than the combined episode totals of Family Guy and South Park. Even King of the Hill, which seemingly ran for forever, only lasted 259 episodes, half of The Simpsons’ epic run.
Whether the show should be off the air is beside the point (though the plot description of Sunday’s episode is, “the Simpsons discover that everyone in town has grown tired of them and are secretly plotting to have them thrown out of Springfield forever,” so they’re commenting on that in a meta way) – I’m instead focusing on the anniversary episodes, the other ultra-hyped episode milestones. The list below is a ranking of the Simpsons’ 50th episode, 100th episode, 150th episode, etc., up to their 450th episode in 2010, listed from worst to best.
#9. “You Kent Always Say What You Want” (May 20, 2007, Episode #400)
Plot: News anchor Kent Brockman gets fired because he said a no-no word live. He moves in with the Simpsons because why not? Lisa instructs him to be a whistleblower on Fox News’ well-known-in-the-industry tactic of getting fined, so the money can go to the FCC and therefore, the Republican Party.
Reason for Ranking: As anyone who watched the recent Ted Nugent-guest starring episode “Politically Inept, with Homer Simpson” can attain to, The Simpsons don’t do political parodies the way they once did. Maybe it’s because we’ve seen them go the obvious Boo Fox News, Boo Republican Party path too many times, but their satires lack edge. There are few things worse than a tame political parody, and they don’t get much tamer than “You Kent Always Say.”
Memorable Quote: “Kent Brockman is threatening our ill-gotten gains.” “Goldarn it! I worked hard to ill-get those gains!”
#8. “Strong Arms of the Ma” (February 2, 2003, Episode #300)
Plot: After getting mugged by a shady-looking character wearing a Goofy hat, Marge is afraid to go outside. While suffering from agoraphobia, she begins to buff up using a weight-lifting kit bought at Rainier Wolfcastle’s bankruptcy garage sale. She soon has two tickets to the gun show (as well as a washboard stomach), and begins taking steroids and terrorizing everyone who loves her.
Reason for Ranking: Marge becoming work-out crazy isn’t a bad idea, but when she meets former-neighbor Ruth “Miss Mexican Mafia” Powers and gets hooked on ‘roids, the episode goes off the rails a bit, without any solid jokes to keep things in line.
Memorable Quote: “What to do now? Too crazy to go outside; not crazy enough to have imaginary friends.”
#7. “Thursdays with Abie” (January 3, 2010, Episode #450)
Plot: A human interest journalist named Marshall Goldman takes a shine towards Grampa and his far-flung tales about onions and belts and bees and old man yells at cloud. Homer becomes jealous of the relationship between his dad and the writer, only to discover that Marshall is planning to secretly kill Grampa to win a Pulitzer Prize.
Reason for Ranking: I mean, read the description above. The B-plot of the episode – in which Bart has to take care of a stuffed lamb for a class assignment – is stronger, and it’s really not that good. A Tuesdays with Morrie parody in 2010 was a decade too late, assuming it should have been parodied at all.
Memorable Quote: “They’ll cheer a dancing octopus, but not an old man complaining about everything.”
#6. “Future-Drama” (April 17, 2005, Episode #350)
Plot: Professor Frink shows Bart and Lisa what they’ll be like eight years in the future, in 2013. Lisa’s dating a jacked-up Milhouse and going to Yale early, and Bart’s dating a girl named Jenda (voiced by Amy Poehler) who wants to have sex with him, which leads to weird thoughts about Simpsons characters doing It.
Reason for Ranking: It’s not the best flash-forward/flashback episode (that would be “Lisa’s Wedding”), but it’s also not the worst (“Bart to the Future). “Future-Drama,” minus a memorable appearance from Bender that didn’t inspire the same hatred from Matt Groening as Jay Sherman arriving in Springfield did a decade prior (wonder why…?), just kind of exists. In other words, it’s a season 16 episode.
Memorable Quote: “We can do anything now that science has invented magic.”
#5. “Trash of the Titans” (April 26, 1998, Episode #200)
Plot: Homer runs for and wins the position of Springfield’s Sanitation Commissioner after getting into an argument with the town’s “trash-eating stinkbags,” a.k.a. garbage men, sanitation workers, whatever you want to call them. The slogan that wins him the election: “Can’t someone else do it?”
Reason for Ranking: Homer gets a new job (jobs, if you include his brief stint as a potato man) and Springfield becomes lazy. There are effective guest appearances from Steve Martin and U2 and a memorable song, “The Garbage Man Can” (not by U2). “Trash of the Titans” has the feel of a classic Simpsons episode, but Homer’s stubbornness prevents it from being one. Season nine is right around when Homer began to change from a real character to a character whose intelligence and mood changed every week, depending on whatever served the plot, and “Titans” is a good example of where you can see the switch happening.
Memorable Quote: “Homer, that crazy lady who lives in our trash pile attacked me again.” “That’s not the way she tells it.” “And the school nurse says Bart has the Plague.” “Eh, it’s like the measles. Good to get it out of the way.”
#4. “A Tale of Two Springfields” (November 5, 2000, Episode #250)
Reason for Ranking: Season 12 is the least consistently great Simpsons season, and “A Tale of Two Springfields” is one of its highlights. It starts with a goofy premise (a badger sets up shop in Santa Little Helper’s doghouse), which sets up the would-be plot (Springfield is split between two area codes), which sets up the ACTUAL plot (the town breaks into New and Olde Springfield). Between the rapid-paced plot and a celebrated guest appearance from the Who (or at least Roger Daltrey, John Entwistle, and Pete Townshend’s brother Paul), this episode proves everyone who says The Simpsons lost it after season eight wrong.
Memorable Quote: “Badger my ass, it’s probably Milhouse.”
#3. “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish’” (April 28, 1996, Episode #150)
Plot: During World War II, Grandpa Simpson and Montgomery Burns were part of a unit known as the Flying Hellfish. Along with Iggy Wiggum and Sheldon Skinner, among others, they “took back” paintings from the Germans at the end of the war and locked them away in a safe. The last remaining Hellfish gets the artwork and the riches that come with them – and after Asa Phelps passes away, all that’s left are Grampa (with some help from Bart) and Mr. Burns.
Reason for Ranking: I used to HATE this episode. Mr. Burns and Abe were two of my least favorite characters, and giving them an entire episode – where they’re fighting against one another – was like listening to the bassist and drummer from matchbox twenty sing instead of Rob Thomas. Clearly by my lame, dated reference, the “used to hate” refers to my teenage years. I’ve since come to appreciate “Raging,” a rare high-concept episode that doesn’t involve Homer.
Memorable Quote: “…And then he claimed he was the one who turned cats and dogs against each other. Why is he always making up those crazy stories?” “Maybe it’s time we put Grampa in a home.” “You already put him in a home.” “Maybe it’s time we put him in one where he can’t get out.”
#2. “Homer Alone” (February 6, 1992, Episode #50)
Plot: Marge has a very public, baloney sandwich-induced nervous breakdown, and it’s decided by the family that she should go on vacation to a relaxation spa, Rancho Relaxo. That leaves Homer to care for Maggie, while Bart and Lisa go to stay with their aunts, Patty and Selma. Horror ensues.
Reason for Ranking: This was one of the first Marge-heavy episodes, and while it has some very memorable scenes (like Barney mistaking Maggie for “little Bart” and Homer calling the Department of Missing Babies) and a tight plot, there’s not a singular great moment in “Homer Alone.” The plot tells a story we already knew – the family falls apart without Marge to keep them together – making the episode feel a little unnecessary in hindsight. But the writing was getting better, and soon after The Simpsons would switch from being a very good show to the greatest ever.
Memorable Quote: “Our tour starts in your very own room, where Relaxo-Vision offers you the latest Hollywood hits. And after midnight, the finest R-rated movies Europe has to offer! Today’s selections are: Thelma and Louise, The Happy Little Elves Meet Fuzzy Snuggleduck, and The Erotic Awakening of S.”
#1. “Sweet Seymour Skinner’s Baadasssss Song” (April 28, 1994, Episode #100)
Plot: Superintendent Chalmers fires Principal Skinner after an incident involving Santa’s Little Helper and a greased-up Scotsman. Bart feels responsible for Skinner getting canned, and becomes friendly with him…in public. Meanwhile, the new principal at Springfield Elementary is none other than Ned Flanders.
Reason for Ranking: To be honest, none of the episodes on this list are all-time worthy. They all have their flaws, but “Sweet Seymour Skinner” has the least amount of them. It poses an interesting question (what happens to a problem student in a school without discipline?) and sets up a story that would be revisited with more depth years later (Ned’s beatnik father), and the interactions between Bart and Skinner are priceless. Plus, none of the other episodes introduce us to Billy and the Cloneasaurus. That’s why it’s #1.
Memorable Quote: “Oh, I have had it with this school, Skinner! The low test scores, class after class of ugly, ugly children…”