The Simpsons: Top 12, If That’s Possible

On Thursday December 28, 2017, my friend Richard Grove and I got together with a lofty, almost foolish, goal: to pick the best 12 episodes of The Simpsons, and watch them all in a row. Not only was the prospect of so much Simpsons all at once foolish in that we would be inevitably exhausted by the end of it, it was mostly foolish because to compile a definitive Best Of list for The Simpsons was, and will always be, totally impossible.

I don’t know that I could ever decide on my very favorite television show of all time, but if truly pressed to pick only one, it would have to be The Simpsons (just barely edging out Mystery Science Theater 3000). I watched it when the first season started airing in 1989, and during their glorious eight-to-ten-season run (depending on your opinion of when the quality dropped off), I was on board the whole time. It started airing in syndication sometime in the mid-90’s, so everyday at 5 o’clock I would watch The Simpsons with a religious devotion.

The Simpsons taught me how to be funny. It taught me what was funny. It taught me about the evils of the world, well before I started learning about that through punk rock. It taught me who to watch out for, and who was full of shit (and it turns out that’s pretty much everyone). Beyond just being a vehicle for Homer to do dumb stuff or for Bart to play pranks, The Simpsons was a vessel for truth, a knife to cut through the curtain covering it.

It is because of all of those reasons that picking the best 12 episodes was never going to be a reality. The list that Richard and I created is not meant to be definitive. Richard and I each picked about 10–15 episodes on our own, and our lists only shared two episodes in common. We could ask tons of other Simpsons fans to make a list, and there still could be little overlap. There are just so many wonderful episodes, each with their own strengths and oddities and charm. So don’t take our list as anything official. It’s just what we were able to cobble together, based on a lifetime of fandom and love.

(episodes are listed and were watched in chronological order)

When Flanders Failed (season 3, episode 3)

Richard pushed for this episode, and I think he did this because of something he said a couple episodes into the day: he believes Homer is an objectively horrible person. As funny as he may be as a character, Homer doesn’t really have any redeeming value. He’s an alcoholic, he’s an abusive father, he rarely encourages his children, he takes every shortcut in life that he can, and he doesn’t help his friends. Whether or not this is meant to be glorified or seen as a picture of the average American, that’s up for debate. But I think Richard might be right in his harsh judgment of sweet Homer.

If any episode proves Richard’s case, it’s “When Flanders Failed.” Ned Flanders opens a store called The Leftorium. For no reason other than pure spite, Homer wishes upon a wishbone that Ned’s store will go out of business. As Homer gets plain opportunities to spread the word about Ned’s store, he never does. And then Ned’s store does fail, his family gets their house foreclosed, and only then does Homer see the error of his ways. He then tells everyone in Springfield about The Leftorium, and Ned’s store starts doing booming business. The episode ends with a literal singalong of “Put On a Happy Face,” with no jokes at all. Richard says this ending is way too sunshiney, and it thinks it absolves Homer of his wrongdoing, but it really doesn’t. Homer’s good deed does not erase his blatant cruelty. And as we see in future episodes, Homer absolutely does not learn his lesson.

Homer at the Bat (season 3, episode 17)

Just months ago, this episode was celebrated at the National Baseball Hall of Fame. Homer Simpson was inducted into the Hall of Fame itself. These honors might sound ridiculous, but I think they’re completely deserved. “Homer at the Bat” permanently etched each of those nine MLB players in an area of fandom which otherwise would never know them. If they weren’t in this episode, I absolutely would not know who Steve Sax or Mike Scioscia are, but they were on the Springfield Power Plant’s baseball team, so to me they are legends.

Every player is totally game for the insane scenarios in which they were placed. Roger Clemens commits to the role of a chicken. Wade Boggs convincingly defends Pitt the Elder as England’s greatest Prime Minster in his argument with Barney Gumble. And Darryl Strawberry is sneakily hilarious as the kissass to coach Monty Burns. It’s a dizzying episode that takes a million twists and turns, and it truly doesn’t have one scene that isn’t brilliant.

Homer the Heretic (season 4, episode 3)

Richard pointed out that even in 1992, the concept of an average American dad refusing to go to church could still be seen as taboo. When Homer announces that his church-free Sunday morning was so great that he’ll never go again, Marge reacts with horror and begs the kids to ignore him. Homer even claims to have a dream in which God told him it was alright for him to stay home. Homer flaunts his newfound heathenism cavalierly, until the house fire in which Ned Flanders saves him and shows him that the people in the church care about him. Moved by this kindness, Homer agrees to go back to church, front row center, where he promptly falls asleep and snores loudly.

As someone who hasn’t attended a Sunday service for my entire adult life, I can still appreciate this episode’s ultimate message, which isn’t necessarily that Christianity is perfect, but that at the very least it provides a sense of community and caring for people who need it. The fact that they were able to convey this message while also totally taking the piss out of religion shows the tightrope which the Simpsons writers were able to easily walk.

Mr. Plow (season 4, episode 9)

There aren’t a lot of emotional reasons for “Mr. Plow” making our list, other than it being an indelible Homer episode that sees him rise to glory and fall back to Earth. He buys a snow plow and starts a business — the rare time when he actually shows initiative to improve his lot in life. Business is good, but when his friend Barney steals his idea, he also steals all his customers. Homer tries to sabatoge Barney, but again, after his evil plans have actually come to fruition, he has a change of heart and saves his friend. Homer can never do the right thing until it’s almost too late.

Among the many highlights here, Richard and I had an unexpectedly huge laugh at Barney’s “Plow King” commercial, which opens with him using a baseball bat to maniacally smash a cardboard cutout of Homer. Barney has to be pulled away, screaming, by two stagehands, and it’s so funny to think of his character seeing this played back to him and approving it for the commercial, believing it will make him look cool and even-keeled.

Lisa’s First Word (season 4, episode 10)

Our first four episodes were Homer-centric, so it was a welcome change to get an episode that focused on the entire family. “Lisa’s First Word” flashes back to the summer of 1984, when Lisa was born. Little Bart hates her, and resents her for his perceived sudden demotion in status. After he cuts off her hair and tries to mail her in a mailbox, Lisa repays him by speaking her very first word: “Bart.”

This episode is not as downright hilarious as the others, but I know why I picked it. The episode ends with current-day Homer putting Maggie to sleep, and sweetly telling her, “I hope you never say a word.” After he leaves the room, Maggie pulls out her pacifier and says, “Dada.” My daughter’s name is Maggie, and this scene, especially today, makes me cry like a baby. I had to seriously fight back the tears in front of Richard. We’re great friends, but I can’t cry in front of him, you know?

Marge vs. the Monorail (season 4, episode 12)

This is one of three Simpsons episodes written by Conan O’Brien, the year before he got his break as the host of Late Night. Conan’s absurdist sensibilities are on display here, as well as the dark cynicism that seeps through his comedy from time to time. When the town agrees to spend $3 million on a useless Monorail system, the scene is littered with subtle and not-so-subtle digs at the American corporate class, and the inherent fallacies of capitalism.

Oh, and the episode is a damn riot. One of my favorites ever. There are genius jokes throughout, Leonard Nimoy plays a pathetic version of himself, but most of all, this one is all about Phil Hartman. I adore Phil Hartman to the depths of my soul, and I think anything he was involved in was wonderful, but here he truly shines as Lyle Lanley, the greedy huckster who sells everyone a line of bullshit with a song and dance. Hartman always excelled when he was at his smiliest and fakest. Here, he’s so good you’d buy anything he offered you.

Marge on the Lam (season 5, episode 6)

Per Richard’s earlier point about Homer being terrible, we both agreed that Marge is a saint. She constantly puts up with one of the worst husbands ever, and finds in him his best qualities. But in “Marge on the Lam”, all it takes is simply making a new friend, and she’s galavanting about the town, leaving Homer to figure things out at home. Homer leaves the kids so he can go to the bar, but he pays terrible attorney Lionel Hutz (another classic Phil Hartman character), to babysit. The kids wake him in the morning and he pulls out a switchblade and screams “Don’t touch my stuff!”, then he looks around and says, “Hey, this isn’t the YMCA.”

Richard and I probably had our biggest and hardest laugh of the day when Homer is in the back of Chief Wiggum’s car, and they’re unknowingly in hot pursuit of a car in which Marge is riding. Wiggum says over the radio, “One is wearing a green dress, pearls and has a lot of blue hair.” We see Homer imagining this and he pictures a horrible monster with a huge green beard and he laughs, “What a freak!” I had kind of forgotten about that part, and I thought I was never going to stop laughing at that, god, it was so good.

$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling) (season 5, episode 10)

I have always held this episode in high regard, as it includes some of my favorite Simpsons jokes ever. Robert Goulet in Bart’s treehouse casino, singing “Jingle Bells, Batman Smells” and then accidentally whacking Milhouse in the face with his microphone. Homer getting spooked by Lisa’s Boogeyman dream and shooting shotgun holes through the bedroom window. Mr. Burns becoming a Howard Hughes-like germaphobe and insisting at gunpoint that Smithers hop into his tiny wooden plane.

I realized upon rewatching that this episode is very scattered. It does have a central plot with Marge becoming a gambling addict and shirking her responsibilities to the family, but the strongest jokes don’t really come from that. This is just a delightfully silly episode with insane jokes, and it draws from all the characters in Springfield. The writers apparently wanted to do an episode that reminds us how Springfield is a lousy place, where no one has any morals, and they did their job splendidly.

Deep Space Homer (season 5, episode 15)

Other than “Mr. Plow,” there is hardly a Simpsons episode in which Homer is given a new responsibility and he doesn’t completely screw it up. In “Deep Space Homer,” he somehow ends up as an astronaut, in a rocket headed to space with 2nd Man on the Moon, Buzz Alrdin. In accidentally saving their mission from destruction, Homer’s accidental efforts are overshadowed by an Inanimate Carbon Rod, which is a joke that would take far too long to explain, but trust me, it’s great.

The most memorable, highly-referenced bit from this episode comes when newscaster Kent Brockman mistakenly believes that giant ants have taken over Homer’s spaceship. He quickly accepts this disturbing news, and in a spineless effort to endear himself to the giant ants, he swaggeringly turns to the camera and says, “I, for one, welcome our new insect overlords.” There are few more incisive Simpsons lines than this one, lampooning our all-too-eager public consciousness to accept our awful leaders and thank them for ruling over us.

Homer Badman (season 6, episode 9)

Almost right as Richard and I started watching this episode, I got a sinking feeling. The crux of this episode is that Homer is falsely accused of sexually harassing a babysitter, and he becomes a hated pariah, until video evidence surfaces and exonerates him. It’s obviously a very touchy time for such a premise, as tons of oafish American men are trying to plug holes in the sinking ship of consequence-free sexual assault. But it seems that the writers intended this to be not so much a condemnation of sexual assault accusers, but rather to hold the mirror up to the crazed media attention that certain stories would get, especially with the Trash TV mentality of the early-to-mid-90’s.

There are many contenders for Best Joke in this episode, but the clear winner is the doctored TV interview Homer does for Hard Copy, in which they poorly cobble together a hit piece that has Homer saying “Her sweet, sweet can” over and over. Helpfully, the show’s producers tack on a hasty disclaimer: “Dramatization: may not have happened!”

A Star is Burns (season 6, episode 18)

My deep affection for this episode probably stems from my deep affection for The Critic — a show created by two former Simpsons showrunners, centering on a short, fat NYC film critic named Jay Sherman. “A Star is Burns” is a rather shameless Simpsons/Critic crossover, which is even referenced out loud by Bart. But when it aired in the spring of ’95, I was elated. I loved The Critic when it was aired, but no one else did. My friends could all quote Simpsons lines with me, but they did not give two shits about The Critic.

I still maintain that this is a spectacular episode, forced crossover aside. It has two all-time Simpsons bits, one being Man Getting Hit By Football, the Hans Moleman-produced short film that his just him getting doinked in the groin by a football, which delights Homer. “It works on so many levels!” But the very best joke, one that still gets referenced constantly, is when Mr. Burns’s self-aggrandizing film is being booed, but Smithers tries to tell him the crowd is actually saying “Boo-urns! Boo-urns!” Burns asks the crowd what they’re saying, and though they confirm that they are indeed booing him, Hans Moleman privately says, “I was saying Boo-urns.” Folks, I couldn’t even type that without laughing until I almost cried. What a beautiful, eternal joke.

22 Short Films About Springfield (season 7, episode 21)

This was another one that Richard insisted we watch, and it’s no slight against him, but I think this is easily the weakest episode we watched. Maybe it was the fatigue of having just watched like six hours of Simpsons, but I found the highly scattered nature of this one to be a little much. The title is barely not a joke — they really do move around between about 20 different plot lines and various characters in the Simpsons universe. As you’ve seen, I prefer Simpsons episodes with a little heart and emotional payoff, and this one just doesn’t have that. I also think a lot of the scenes are average, but not awesome.

Even Richard might admit that he mainly picked this episode because of the bit between Principal Skinner and Superintendent Chalmers, in which Skinner hosts Chalmers for lunch at his house, and everything goes wrong. He burns his turkey, ultimately burning down his home, but before that he tries to pass off Krusty Burgers as “steamed hams,” and then covers up for the fire in his kitchen by telling Chalmers it’s Aurora Borealis. The back and forth dialogue between Skinner and Chalmers is truly nutty, truly inspired writing, and I agree with Richard that it’s one of the better moments we watched all day. But yeah, kind of a dud of an ending to the day for me.

***

And really, we got what we deserved. We were exhausted, delirious, our faces hurt, and we were obviously no closer to determining the best Simpsons episodes of all time.

If you’re reading this, and you feel like you’re as big a Simpsons devotee as Richard and I, please tell us some of your favorites, and we can debate and laugh and enjoy our existence, because it’s slightly better for having The Simpsons in it.