The Simpsons: 10 Funniest Episodes Ever Made
7. 22 Short Films About Springfield (Episode 21, Season Seven)
What's the point of being a writer on The Simpsons if you can't outright indulge yourself now and again and shake things up? That's the feeling that drives one of the show's funniest episodes ever, 22 Short Films About Springfield, which serves as something of a parody/love letter to art cinema whilst throwing out brilliant joke after brilliant joke.
The episode, as one might gather from the title, is made up a series of vignettes, all of which are connected (a nod to Quentin Tarantino's Pulp Fiction, which came out a year before this aired and is probably the part of the episode that people remember most). The whole thing is absolutely barmy, but the brilliance lies in the fact that every vignette is hilarious in its own way; each one resonates and sticks with you like a short film might.
The best story? The one that sees Principal Skinner hosting a very sitcom-esque dinner party for Superintendent Chalmers, which of course goes tragically wrong (complete with theme song). This segment also gave Simpsons fans the now infamous "aurora borealis" conversation, which is one of the most ludicrously funny moments in the show's history.