5x19 Sweet Seymour Skinner's Baadasssss Song

[7.4/10] I don't know if this was planned or intended to be the show's landmark 100th episode, but regardless, I like that this one focused on a bit of a deconstruction, or at least a deepening, of the relationship between Skinner and Bart. Their Roadrunner/Coyote dynamic through the show has been a continuing source of humor, so it's nice to see the show mine it to add new dimensions t both characters and make their connection a little more complex at the same time.

The episode is structured really well, with Bart bringing SLH to school snowballing into a school-wide crisis nicely in the first act, Bart's budding friendship with Skinner developed in the second act, and the plan to oust Flanders and get Skinner out of the army falling into place in the third act. But more than that, I really appreciate how well-observed the awkwardness and ensuing warmth between Bart and Skinner is. There's something so weird about seeing a teacher outside of school, and coupling that with Bart feeling guilty for what he did to even his worst enemy leads to some really nice material.

There's also so much great humor, which I more or less take for granted in this era of the show. The ironing is delicious in Bart declaring that it's unlikely that anyone will be laughing at something he's done in twenty years. Marge explaining her appreciation for potatoes as "I just think they're neat" is a quote that gets tossed around a lot in the Bloom household. And Ned as principal is just a font of comedy, between the crazy state of the school under his watch, the lame but uproariously received puns at the assembly, and his flashback to his beatnik-parented childhood.

Overall, it's a softer, sweeter sort of Simpsons episode, that takes a down-to-earth but really engrossing premise of school grounds enemies becoming friends, builds in backstory and shading to Skinner (the fact that the army is the only other place where square Seymour fit in is a really nice touch), and packs in the laughs all the while. I'm always amazed at how well even this show's less flashy or memorable episodes are so great.

(As a personal aside, I watched this one while flipping channels in a hotel room on a trip for a wedding, and there was a strange comfort to it. Traveling is nice, but there's always something that feels a little foreign about not sleeping in your own bed or being in unfamiliar surroundings. Seeing some old Simpsons episode on the television is this nice bit of yellow-tinged familiarity, a reminder that wherever in this country you go, you can channel surf and find the denizens of Springfield, always there to make you laugh. It's odd to take that sort of comfort in a TV show, but it's nice nonetheless.)

Of all the countless Simpsons episodes that I have seen over the years, I have to say it's this one that tops them all for me. The fact that this is also their landmark 100th episode makes it all the more special and it's also the episode that cemented Skinner as one of the best written characters in the entire shows history... well at least until Season 9 anyway. It's an episode with so many timeless moments. It has some of the most timeless jokes, it sets up lots of fun character arcs in seasons to come, and most of all it has one of the shows greatest strengths.... heart.

It starts of with Bart struggling to find a project for his schools "Show and tell" class, and he winds up bringing the dog to school, which eventually leads to Skinner getting fired and him feeling remorse for it. What works so well in this episode for me is that Bart's actions aren't really set up like a cruel prank like it normally would be. Instead he just does something wreckless and thoughtless which inadvertently got Skinner fired. His remorse for his actions feel completely ernest because of this, and I love that complex dynamic that is with his natural arch-nemesis. Until this episode they was written as polar opposites, Bart the natural hell-raising rebel and Skinner the strict no-nonsense principle, yet their friendship shown through the episode really does feel genuine.

Skinner on the other hand, his job is his entire identity. No longer being principal of the school feels like it takes all purpose out of his life, something he now has in common with Bart as Bart has no establishment to rebel against with Skinner being replaced as principal with the pushover Ned Flanders. There are several comedic moments in earlier episodes where Skinner is shown to be traumatised by his time in the military and the control from his mother. Skinner is completely unravelled and shown at his most vulnerable in this entire episode and it is tragic and yet strangely beautiful to watch.

Though the plot itself might seem morbid and detached in the way I describe it, it still has some of my favourite jokes. Who could ever forget lines like Groundskeeper Willie saying "Well grease me up woman" or the scene in the vent that parodied the first Alien movie. It has one of my favourite Apu moments of all time when he finds out Skinner is about a novel that plagiarises Jurassic Park and goes on a long rant that has two time skips! Or what about that Ned Flanders flashback about his beatnick father which would be expended on further in the Season 8 classic "Hurricane Neddy". Watching Chalmers over the top reaction to Ned Flanders praying, but not really caring at all about how the chaotic school is, is just comedy gold.

I don't think the infamous Season 9 episode "The Principal and The Pauper" is as bad to watch as some of the truly awful episodes like Season 23's "Lisa Goes Gaga", but to me it felt so wrong because it came at the expense of some of the wonderful character development Skinner got from episodes like this one! It should never be forgotten however that in the golden ages of this show that THIS was the kind of writing we expected. It is one of the most perfect episodes in the shows history and one of the best 20 minutes of animation ever made!