Suggested Simpsons Syllabus

A bundled dozen episodes I'm recommending for a curious first-time viewer.

A reader asked in a comment on an old newsletter for five or ten recommended episodes of The Simpsons because she’s never seen any in entirety. I said five is unrealistic so how about ten and what if for a constraint I chose one from each of the first ten seasons. She said deal.

However Season Ten is just too much of a snoozefest and doesn’t have an offering that wouldn’t be a waste of a slot when the second through eighth seasons are so overstuffed with great material. I also struggled to fit in enough episodes that balanced the contrasting personalities of the four principal family members with episodes that stand out for their uniqueness or inventiveness while also including at least one “Treehouse of Horror” and Sideshow Bob episode. So I’m going to exercise my prerogative to choose one from each of the first NINE seasons and then an additional three for a tidy dozen. Like it or lump it.

• Season One, Episode Four, “There’s No Disgrace Like Home.” With the garish, arresting, punky look of the first season comes an episode that well establishes the neurosis and dysfunction of the Simpson family. It also hits a few key points that are important later in the show like Homer’s difficulties with his working life and his habit of hiding from his troubles in Moe’s Tavern. It ends with one of the program’s early standout sequences of cartoony overwhelm when the Simpsons prove too antisocial and decency-averse to be cured through professional help — which paradoxically brings them to a place of unified self-acceptance. A good episode for establishing that these are economically and socially struggling people who love one another as family but have to work to find healthy ways to express it, with no satirical quarter given to the pretensions and excesses of trendy Nineties therapy culture.

• Season Two, Episode Eighteen, “Brush with Greatness.” Explores aspects of Marge and Homer’s personalities in greater depth, provides a closer look at Homer’s challenging relationship with his boss and features two noteworthy guest appearances: Jon Lovitz as one of the various characters he’s played over the show’s run and Ringo Starr as himself, the first of all three then-living Beatles to make apperances on The Simpsons. A fun and moving episode demonstrating grace and complexity.

• Season Three, Episode Four, “Bart the Murderer.” I decided to go with a great episode which also happened to be the first episode I ever watched in entirety, during its original television broadcast. It’s a rather dark turn for the show which actually frightened and stressed me out as a child who was watching past his bedtime while his parents were entertaining dinner guests. However this was where my obsession with the show itself, and not just with the concept and image of Bart Simpson that was then flooding the cultural marketplace, really began. This one has great writing (by the legendary John Swartzwelder), clever animation and the first appearance by great actor Joe Mantegna as Springfield mafioso Fat Tony.

• Season Four, Episode Twelve, “Marge vs. the Monorail.” I struggled with which to choose of the unbroken string of gems comprising the fourth season so I’m playing it relatively safe with an episode that was written by Conan O’Brien (of whose I went on to become a devoted fan during his run on Late Night with Conan O’Brien and later on his podcast Conan O’Brien Needs a Friend), plays ingeniously with the growing scale of the show’s cast of smalltown eccentrics and features a one-of-a-kind guest appearance by the legendary Phil Hartman. It also has one of the program’s most beloved musical numbers.

• Season Five, Episode Five, “Treehouse of Horror IV.” I felt that for the purposes of this survey it was important to get in at least one of the show’s annual Halloween specials and this is one of the finest. Probably the second best after “Treehouse of Horror V” but Season Six is too densely excellent and I had to pick others:

• Season Six, Episode Four, “Itchy and Scratchy Land.” The whole family out on an adventure together at an exotic theme park. Rich with parodic allusions, amplified by a thrilling climax, beatifully animated and screamingly funny.

• Season Six, Episode Five, “Sideshow Bob Roberts.” As I said above I wanted to get in at least one episode centered around Kelsey Grammer’s recurring villain/antagonist Sideshow Bob and this may well be the best one, a blistering satire of party politics that takes deadly yet admirably even-handed aim at the GOP and Rush Limbaugh and also gets in stirring parodies of All the President’s Men and A Few Good Men. Grammer was never better as the bitter, vengeful, mellifluously-voiced and over-educated Sideshow Bob. This episode is thoroughly characterized by the animation look I like the best, the relaxed but sprightly aesthetic of Seasons Six through Eight.

• Season Seven, Episode Sixteen, “Lisa the Iconoclast.” Doing some of what the show does best: mining its own mythology to find new depths of moral insight and to model good storytelling by leading us to a conclusion that is both surprising when it arrives and inevitable in retrospect. This is possibly my favorite Lisa-centric episode ever because it shows her at her finest — conscientious and civic-minded but nonconformist and diligent in her commitment to following the truth into whatever uncomfortable places it leads. Outstanding guest appearance by Donald Sutherland. Beautiful animation.

• Season Seven, Episode Nineteen, “A Fish Called Selma.” An episode that makes a genuinely moving story out of a lesser character’s sincere struggle to invite love into her life and also does some killer riffing on the phoniness and cynicism of Hollywood culture. Phil Hartman returns in an extended appearance as one of his recurrent roles on the show, the washed-up film actor Troy McClure. Narrow but laser-sharp guest turn from Jeff Goldblum. This one has several of the most achingly funny laughs the show ever earned, including in an extended musical sequence that expertly parodies what a Planet of the Apes Broadway musical might look like. The night I correctly answered the game-winning lightning round question at the Simpsons trivia pub quiz the winning team was permitted to pick the last episode that the bar projected on the big screen after the game was over, and since I had answered the question my team deferred to me. I chose this one.

• Season Eight, Episode Nine, “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer).” Some of the weirdest material the show ever produced without compromising narrative integrity. This one makes the list just on the sheer gumption in the risky storytelling and psychedelic animation showcase. And it has one of the best uses ever of a high-profile guest performer with none other than Johnny Cash playing a mystical “Space Coyote” who appears to Homer in a hallucinatory dreamscape. A true oddity that also works admirably along the lines of a conventional episode.

• Season Eight, Episode Fifteen, “Homer’s Phobia.” See previous bullet point: in another essay I’ll be getting into why Season Eight is the most experimental and self-referential season of the program and would have made a perfect last season for the show to go out on. For now I’ll just say that this one is meticulously constructed with several layers of meaning, the most important of which is that Homer is revealed to be an anti-gay bigot and that the show confronted this bias in one of its central characters with elan. And with a marvelous guest appearance by John Waters.

• Season Nine, Episode Three, “Lisa’s Sax.” This is the only episode from the ninth season that I really like without qualification. I think it’s very good all around with a crisp look that is superior to the rest of Season Nine; it looks and feels like it would have fit in better in the season before. Perhaps I remember reading somewhere that it was in fact a holdover from the eighth season. In any case it’s solid and I’m also glad that there’s one of the show’s signature family flashback stories on this list; that’s one of the many things that an animated program can get away with in convincing and clever ways that a live action show can’t.