Nobody has the same “Top Simpsons Episodes” list. Everyone’s top eight is different, everyone’s top 50 is different, and anyone who picks any episode from seasons 3 to 8 is correct. But these eight are more correct than any of the others. I embiggen anyone to prove otherwise.
Grade School Confidential (Season 8, Episode 19)
The love story of Seymour Skinner and Edna Krabappel is simple and sweet. The writers managed to identify what was charming and likable about each character, so when these two cartoons fall for each other, you buy it. And when it falls apart, “Grade School Confidential” offers one of the best bittersweet endings The Simpsons has ever had. Skinner and Krabappel’s last dance in the school is romance done right, and Skinner’s earnest and heartfelt thank you to Bart is a moment of simple honesty that I really love.
Best Jokes: “The bake sale to raise money for the car wash has been canceled due to confusion.” “I’ve been calling her Crandal! Why didn’t someone tell me! Oh, I’ve been making an idiot out of myself!”
Marge on the Lam (Season 5, Episode 6)
Like most mothers, Marge is by far the most selfless member of her family. Most of the time, she’s content to devote her entire life to her kids and husband, and she very rarely pursues much of a life outside of them. That’s why her adventure with Ruth feels so cathartic, and why her grabbing the wheel at the episode’s climax feels like such a triumph. And I haven’t even mentioned the Homer/Wiggum or Kids/Lionel Hutz A+ side plots.
Best Jokes: “Engine black eggs…if we can keep these down, we’ll be sitting pretty.” “It’s a ghost car!”
A Milhouse Divided (Season 8, Episode 6)
The dinner party that marks the last straw in Kirk and Luann’s marriage is just brutal. From the second they walk in the door, they’re a painful picture of an unhappy couple, and while it’s surprising when Luann demands a divorce, it felt inevitable. The episode's best comedy comes from sad-sack Kirk and self-actualized Luann, but what really makes it shine is how Homer uses their divorce to reflect on his own relationship and reaffirm his own love for his wife.
Best Jokes: I nominate two visual jokes. Bart lying on the floor, eating dinner in his underwear, and Bart hitting Homer with a chair while he sits in the tub.
Sweet Seymour Skinner's Baadasssss Song (Season 5, Episode 19)
Principal Skinner is the best secondary Simpsons character, and this is the best Skinner episode. Making Bart and Skinner friends seems like a pretty hacky concept for an episode, but it works because Skinner is just so kind and sincere (if still hilariously lame). Of course, Skinner getting his job back achieves the sitcom requirement that everything ends up back where it started—but the “Teach me” sign on Bart’s back shows that their friendship helped Skinner grow as a person, if just a tiny bit.
Best Jokes: “Did you just call me a liar? / No, I said you're fired. / Oh...that's much worse.” “I can buy another pair...No, I can't. I needed those, I really did.”
Summer of 4 Ft. 2 (Season 7, Episode 25)
From a pure storytelling perspective, this episode is just immaculate. It all starts with the yearbook, which serves as a literal symbol of Lisa’s nerdiness (it details all her clubs and awards) and her alienation (everyone refuses to sign it). It prompts her to change her whole personality, leading to hands-down the coolest outfit any Simpson has ever worn (Sorry, Colonel Homer). Then, in the end, Bart tries to use that same yearbook to scare off her new friends—only to have them affirm that everything Lisa thought made her lame, actually makes her great. And of course, the episode ends with Lisa, staring at her yearbook once again, only this time it’s filled with her friends' words of love and support. It’s perfect.
Best Jokes: “The leatheroleum covers were worth the extra money—you can smell the benzene!” “See you in the car! Best wishes, Milhouse”
And Maggie Makes Three (Season 6, Episode 13)
Okay, this is one of the obvious top emotional moments in The Simpsons, but I don’t think people really appreciate how funny “And Maggie Makes Three” is. It’s got Knight Boat for crying out loud! Go Knight Boat, go! Looking back, you tend to remember the heartfelt moments—Homer falling in love with Maggie the second he sees her, him filling his office with photos of her to remind him why he works his dead-end job—but what made The Simpsons so special is that it managed to pull off those moments without sacrificing one inch of comedy. God, this episode is just so funny, go watch it right now.
Best Jokes: “Bowling! Bowling here! Come bowl now! Get your bowling! Who’s ready? Bowling!” “Aaronson and Zowkowski are the two biggest gossips in town...”
Bart’s Comet (Season 6, Episode 14)
I love every minute of this episode. I love Bart’s prank weather balloon. Skinner’s hilariously futile stargazing. The nicknames of every last nerd. Homer twiddling his thumbs for way too long. The whole town arguing in Flanders’ bomb shelter. All of Springfield coming together to accept whatever fate has in store for them. Que sera sera. There are funnier jokes in other episodes. There are more emotional endings. But “Bart’s Comet,” from start to finish, has everything that makes The Simpsons great.
Best Jokes: “Hurrah for science woo? Well, I can’t say I approve of the woo, but the hurrah was quite heartening.” “This is Email, Cosine, Report Card, Database, and Lisa.”
Lisa the Vegetarian (Season 7, Episode 5)
Years ago, I asked a friend what she thought the best Simpsons episode was, and she said, “Lisa the Vegetarian” without hesitating. I thought she was nuts. I told her she was nuts. She replied, “Just watch the episode. It doesn’t go 30 seconds without an all-time funny joke.” So I did. And she was right. “Lisa the Vegetarian” might be the most jokes-per-minute of any Simpsons episode, and it still manages to lead to a tear-jerker emotional resolution (though, to be fair, “Maybe I’m Amazed” is a cheat code for happy endings). It's the best episode of The Simpsons. And if you think it was a different one? You're probably right. It was a very, very good show.
Best Jokes: “Don’t let the name throw you Jimmy…it’s not really a floor!” “You dunkin’ your sausages in that syrup there Homeboy?”