Picking the five best Simpsons episodes is well-nigh impossible.
Even if you accept that basically nothing from season nine onwards is going to match up to anything in the first eight seasons (despite seasons nine and onwards having a few choice episodes), you still have to contend with the sheer amount of classic episodes in those first eight seasons. The Simpsons were the cultural institution of the 90s, for better or worse, a touchstone of a whole generation (Slate.com press critic Jack Shafer has argued that we’ll know that baby boomers have ceded control of the media to younger generations when Simpsons quotes start turning up in headlines).
For those who grew up in the ’90s, The Simpsons became the lingua franca of life. When I was in college from 1999 to 2003, Simpsons quotes or references became a kind of conversational shorthand, a way to sound clever on dates, or a way to size up whether the person you were talking to might be the very best kind of friend. It was a common denominator, one of the few things everyone knew about and could agree on. Saying “My cat’s breath smells like cat food” wasn’t just leeching off of someone else to be funny; it was both an ice breaker and a quick way to signify that you didn’t completely suck. And that was in rural South Dakota! Surely the phenomenon was more pronounced elsewhere; TV writer Denis McGrath has talked about how TV writers rooms often descend into long Simpsons quote-a-thons.
Aside from my top choice, the rest of the lineup could change on any given day. If anyone has the exact same list as me, I won’t only be shocked, I’ll be a little frightened. This is all an elaborate preamble to saying that picking the very best is impossible, so I singled out episodes that I think exemplify some of the things the show does best (and I made an effort to pick only one episode per season—otherwise, I could have filled the whole thing with Season Four entries). So, in the wake of the titanic success of The Simpsons Movie (a work that doesn’t rank with the best-ever episodes, but sits comfortably enough on the second tier—which is a pretty damn great tier), here are my five.
1. “Marge vs. the Monorail” (season four, episode 71, originally aired Jan. 14, 1993): “Marge vs. the Monorail” is the prototypical Simpsons episode. It’s the one you think of when you think of a Simpsons episode. It has a slew of great, quotable lines, a plot where Homer’s stupid but not offensively so, a collection of cultural references that cut from The Music Man to Star Trek to old movies where disembodied heads float around the protagonist’s head and one terrific musical number. Written by Conan O’Brien and directed by Rich Moore, the episode features a star turn by Phil Hartman, who was practically a regular until his untimely death in 1998, as well as a good-natured cameo from Leonard Nimoy.
What really works about “Marge vs. the Monorail” is its use of the town of Springfield to satirize America at large. Sure the show had done this before and has done it since, but this episode crystallizes the mob mentality of Springfield, the town that never met a dumb idea it didn’t like (the escalator to nowhere, for one). Springfield’s town meeting to decide what to do with an unexpected boon from Mr. Burns goes from bad to worse, even as Marge presents a perfectly reasonable idea of what to do with the money (which is co-opted, somehow, by Grandpa). The show’s absurdist streak is in evidence throughout; the episode revels in the surreal-yet-somehow-grounded humor that fueled the series’s best seasons.
To a degree, you can see what would eventually bring The Simpsons back to mere mortal status throughout this episode. The satire’s a little broad and the action zips from place to place with little to no time for the heartwarming moments that have always made the show something of a sucker punch in disguise. But the episode is maybe the show’s funniest, and it most perfectly encapsulates what may be the show’s overriding theme: People are really stupid and self-serving, but if you give them long enough, they’ll eventually bumble toward the right answer. Never mind that the episode made a viable form of mass transit seem silly; it’s the one I still quote the most.
2. “Lisa’s Substitute” (season two, episode 32, originally aired April 25, 1991): From one end of the spectrum to the other. “Lisa’s Substitute” is far more indicative of the show’s first three seasons, when James L. Brooks was more of a presence in the writers room, than the seasons that followed, when he moved on to other commitments. Occasionally, The Simpsons’ efforts to reach for the heartwarming moment can feel cloying, but in its early years, the show often felt surprisingly realistic in its depiction of a blue-collar family struggling to make ends meet and occasionally growing frustrated with the inabilities of their fellow family members to be as compassionate as possible. The show’s heartwarming moments worked in the early years because it wasn’t always a given that Lisa would forgive her father or that Marge would take Homer back (the women in this family are much more capable than the men, on average). The angers and frustrations of family life sprung from a real and occasionally dark place. It also helped that the show was mostly realistic, having not wholly given in to the cartoon physics and fantastical universe that dominated later seasons.
“Lisa’s Substitute” also boasts a great guest turn from Dustin Hoffman (credited as Sam Etic) back when the show’s guest turns weren’t announced in pre-season press releases (and back when they were parceled out based on need instead of a desire to fit into the formula of the series). Hoffman’s work makes the unconventional substitute teacher Mr. Bergstrom more than just the Dead Poets Society cliché he could be. His chemistry with Lisa is real, and his final lesson to her (a piece of paper bearing the words “You are Lisa Simpson”) speaks of Brooks’ good-hearted sentimentality at its best. It doesn’t hurt that the episode is also very funny, featuring probably the finest moment for schoolyard ponce Martin Prince when he runs against Bart for class president.
3. “Flaming Moe’s” (season three, episode 45, originally aired Nov. 21, 1991): In addition to being a very funny episode and containing one of the most-quoted bits in the show’s history (Homer’s “making people happy” monologue), this episode stands as an example of the show gradually expanding its supporting townspeople into characters in their own right. Moe was just an angry bartender before this episode. After this one, he’s the sad man who sometimes tastes success but always lets it slip away because of his inability to do the right thing until it’s too late (he’s like a lot of the characters in the show in this regard). Starting in season three, the show broadened its scope beyond the central family and turned many of the townspeople into fascinating characters in their own right, a move which has ensured the show longevity (even as it occasionally seems unfocused).
The episode’s also a frank look at the tensions that were unraveling the trio that made the show what it was (if you believe the stories). Creator Matt Groening came from the world of alternative comics, and his ready-made cynicism informed the show’s pessimism about life in these United States. James L. Brooks wed this to a family sitcom structure and the kind of heart he brought to classic sitcoms like Mary Tyler Moore and Taxi. And Sam Simon was the man who was the show runner in the first three years, blending these two strands of humor into the show we know today and training a comedy dream team of writers (who were mostly untrained in writing for television). Though Groening or Brooks’ accomplishments shouldn’t be besmirched, Simon often felt that he was not given enough credit for what made the show work. He left the show at the end of the third season, and this episode may be his most-remembered expression of his frustration—even if his name doesn’t appear on the script.
4. “Cape Feare” (season five, episode 83, originally aired Oct. 7, 1993): I could have gone with a “Treehouse of Horror” episode, but I’ve never found one I liked completely. Instead, I’m going with another installment in the series other long-running storyline—the tale of Bart’s showdown with the villainous Sideshow Bob. The Sideshow Bob episodes (featuring the sterling voice work of Kelsey Grammer as Bob) seem to take place in some other continuity from the rest of the series, but this one is probably the best, racing as it does from serial killer movie parody (and more specifically “Cape Fear”—the Scorsese version—parody) to gloriously funny throwaway jokes. Everything from the epic rake gag to Homer’s inability to understand that he’s Mr. Thompson works here. And the episode also scores with a completely ludicrous but perfect action movie climax.
5. “King-Size Homer” (season seven, episode 135, originally aired Nov. 5, 1995): Any number of episodes could have filled this final slot—from the original and daring “22 Short Films about Springfield” to the fan favorite “Lisa’s Wedding”—but one thing The Simpsons has always done well is good, cartoony gags. Bill Watterson (creator of Calvin & Hobbes) once said that he tried to get the words right before the pictures, but if he couldn’t find a good joke through dialogue, he would go for broke on funny pictures. And while there are a lot of funny jokes in this episode (including Homer’s fingers that are too fat to dial), the best thing about it is the sight of Homer, weighing well over 300 pounds, dressed in a muumuu and a “fat guy hat.” The climax is a little forced and cartoon-y (as are many climaxes from the show’s later seasons), but Homer’s weight gain works so well visually that the episode gets away with a lot more than it might.