Top 10: Simpsons Episodes

Everyone loves a good Top 10 list, right?  With this in mind, my good friend Ryan Lambert, he of The Two-Line Pass blog and a writer for Yahoo’s Puck Daddy hockey blog, recently took it upon himself to come up with “the best” ten episodes of “The Simpsons” ever made.  Considering he is quite the “Simpsons” aficionado, this has to be the best ten period, right?  Enjoy, and debate the list’s merits in the comments….

Recently I had a discussion with a friend of mine about what is the best Simpsons episode. We could not come to an agreement, as, I’m sure, could most people who are deeply devoted fans to a show that has been on television since 1989.

But “The Simpsons” has a somewhat unique problem: Any show that has been on television for 20-plus years is going to turn bad at some point, and while many fans may disagree with me, I personally find that point to be at the conclusion of its eighth, and greatest season. There are some highlights in Seasons 9 and 10. There are none, that I’ve seen, after that.  [Ed. note:  this is 100% unadulterated fact]

It’s odd, I guess, that the show has been unwatchable to me longer than it was ever good. But the highs, most human beings would agree, are dizzying. The lows — and I can only imagine the depths to which they’ve sunk in the 13 years in which I have not seen a single new episode— are cavernous (“The Simpsons are going to Papua New Guinea!”). But the episodes I’ve seen have been watched, I’d wager, dozens if not hundreds of times. When I was a kid, there were three stations that played the show in syndication every weeknight. Usually, there were four a night to be viewed if I was so inclined: 5 or 5:30 p.m., either the full 6 or 7 o’clock hour and 11. Most nights, I was so inclined.

There was just something about the show. Maybe because I was six when it started, just two years Bart’s junior and enamored of the way his “Eat my shorts” attitude was so irksome, to my grandmother especially, who was unswayed by my requests that she not have a cow over the show’s use of language or adult situations.

I grew up with the Simpson family from ages 6-15 or so, awaiting every new episode with rapturous anticipation, poring over the old ones for jokes I didn’t get upon first viewing (and there were many) or finding new depth to characters I took for granted.

These, then, are the 10 greatest episodes of the greatest show of all time (if you discount that terrible final 14 seasons). You will find that my list is littered either with episodes that provide considerable emotional depth to Our Favorite Family, or else are completely batshit insane. I have no time for stuff in between.

10. A Streetcar Named Marge

This was one of the first episodes I ever watched and really understood that these were more than cartoon characters. They were almost people. I suppose I didn’t get the very, very clear parallels drawn between Marge and Blanche DuBois, but then most 10-year olds don’t read Tennessee Williams plays.

9. Homer’s Phobia

While the Simpsons wasn’t the first show to have an openly gay character on it (I’m looking at you, Scooby Doo Mysteries character Scrappy Doo), it was one that dealt with homophobia in an alarmingly direct way. Any time a show has a character, in this case television arch-ass Homer J. Simpson, profess that he likes his beer cold and his homosexuals, “fuh-laming,” it is, perhaps, too frank for people to ignore. This was also an insane episode because it ended with a reindeer attack being quelled by a Japanese Santa robot controlled by an impossibly gay man.


8. Sweet Seymour Skinner’s Badassssss Song

I don’t know why, but I love a Principal Skinner showcase. He’s a character that has significant depth but also can be funny in several different ways. In particular, the episodes in which Bart is forced to become close to him for some reason or another are among my favorites (clearly). This episode, in which Skinner is fired for having a school with low test scores and class after class of ugly, ugly children, showed that he wasn’t simply a foil to Bart’s half-assed acting out, but an actual person.


7. Bart the Lover

Another story in the same vein as the previous: We find out that Mrs. Krabappel, Bart’s teacher, is a terribly lonely divorcee made miserable by the awful children that attend Springfield Elementary. So Bart, serving detention as he so often does, constructs a pen pal love interest named Woodrow (and depicted with an old photo of Mr. Hockey Gordie Howe). The theme of shading in secondary characters’ backstories was established early in the show’s run, and nearly perfected here. It would later spiral out of control, of course, ultimately leading to the terribly unfortunate Armin Tamsarian episode that led me to quit the show forever.


6. Homer’s Enemy

Finally we come to an absolutely absurd one: Frank Grimes is a character constructed specifically to react to Homer’s buffoonery in the way a person from the real world would. But his background, from nearly dying in a silo explosion to earning money as an orphan boy by delivering toys to rich children, is just tragicomedy at its finest. That he ultimately dies because he believes he can endanger his life the way Homer does on a daily basis serves as an hilarious reminder to the kids out there: Don’t be a fat idiot.


5. Life on the Fast Lane

I didn’t get it when I was a kid, but this is a Season 1 episode is short on laughs and an absolute masterpiece. That they did a story in the first season of the world’s first primetime cartoon show since the Flintstones about being tempted to cheat and in doing so destroy a marriage and a family was incredibly bold. That the episode came out this stylized (Marge’s fantasy sequences in particular are simply beautiful) and emotionally resonant showed where this show was headed.


4. Grade School Confidential

Well if I liked Bart helping Skinner be less depressed in unemployment, and Bart helping Krabappel be less lonely, then surely I was going to like the episode in which he helps them come together as a couple. This episode had a ton of big laughs and great lines (“I saw the baby and the baby looked at me!” –”THE BABY LOOKED AT YOU?!”), but also the personal element (the sequence in which the couple dances in the cafeteria lit by the light through the colander is incredible visually and otherwise) that typifies so many of the best Simpsons episodes.


3. The Way We Was

The perfect flashback episode against which all flashback episodes for every show since must be measured. This is Marge and Homer’s origin story, and we see just how the couple fell in love and had to get married in a hurry due to an unplanned pregnancy. The show tried this several times over the years with Lisa’s First Word and And Maggie Makes Three to recapture the magic here, but I’m sorry, you’re just not going to top an onion engagement ring or impregnating an 18-year-old in a minigolf windmill you’re supposed to be operating by hang.


2. You Only Move Twice

The greatest of all the completely off the wall episodes: Homer quits his job at Springfield Nuclear Power Plant, working for the openly evil Mr. Burns, to take a position with Globex, working for the covertly super-evil Hank Scorpio, with whom he shares an odd bond and love for saying goodbye to a pair of shoes. There’s another of Homer’s lifelong dreams, Tom Landry hats, there’s not giving you my coat, there’s Marge nursing a secret alcoholism. I don’t know what else someone could want.


1. A Milhouse Divided

As exhibited above, I have a love of both emotionally heavy episodes and those that are light to the point of unabashed silliness. This episode, I feel, perfectly mixes the two. Milhouse’s parents get divorced, and while the toll it takes on Bart’s best friend is just soul-crushing and very real, the divergent paths of his unfortunately-similar-in-appearance parents are hilarious. Luanne becomes the stereotypical newly-divorced woman, dating an American Gladiator and letting her obviously emotionally damaged child do whatever he wants. Meanwhile, Kirk becomes the stereotypical sadsack newly-divorced man. He sleeps in an unfurnished bachelor apartment in a child’s race car bed, dates a woman who uses him and steals his car, and records perhaps the worst song of all time, “Can I Borrow a Feeling?” This episode is everything The Simpsons ever did right, done to absolute perfection. I will never not laugh at Kirk’s Pictionary drawing of a door. “USE IT!”

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