Earlier this week, I posted something on The Simpsons and realized that it was the first post that I had written personally for this site that I had done on the show, which just so happens to be, not only my favorite show of all-time, but one of my biggest influences.  On another site, I posted my Top 40 Favorite Simpsons Episodes of All-Time in conjunction with the 500th episode airing. I figured I’d post those postings by fives here, as well.

#40: The Springfield Files

Original Air Date: January 12, 1997

PLOT: Homer’s alien sighting sparks an investigation by Mulder and Scully from the X-Files.

In 1997, I was a huge fan of both The Simpsons and The X-Files, so I was highly anticipating this episode. And this crossover did not disappoint. The voiceover work of the guest stars was fantastic. Gillian Anderson, David Duchovny, and Leonard Nimoy were each hilarious in their own way. Each of them seemed to have a good time with the material and lampooned themselves quite nicely.

The most memorable scene in this episode is easily the battery of tests that the X-File team puts Homer through. From the exploding lie detector to the treadmill, its the Simpsons at its best.

#39: King-Size Homer

Original Air Date: November 5, 1995

PLOT: Homer gains 61 pounds in order to go on disability and work from home.

This is Homer at his most scheming. This is just the kind of thing that Ralph Kramden would do, had he been a cartoon character and able to gain 61 pounds in the time it took to film an episode.

This episode had me at Homer in a muumuu, really. Its not every episode that you see a character off-model, and here we get it not only in different clothes, but also… well, king-sized. Its also an episode that calls back to the water-drinking bird toy from the second Herb Powell episode, which is hilarious in its own right.

#38: Two Bad Neighbors

Original Air Date: January 14, 1996

PLOT: George H.W. Bush moves in the Simpsons’ neighborhood and Homer immediately hates him.

In what remains to this day one of the Simpsons most “Meta” episodes, the hilarity here is very situational. There’s not a whole lot of laugh-out-loud moments and is quite a departure from most Simpson episodes. It’s one of those episodes in which Springfield meets real life. Much like in “Homer’s Enemy” an outsider comes in and raises a cocked-eye brow at the status quo of the burgh, primarily at the Simpson family.

Here, its former president George Bush who doesn’t treat Homer like the precocious man-child everyone else seems to have grown accustomed to nor does he appreciate Bart’s neo-Dennis the Menace antics. The episode winks at this persona as Bush becomes more of a parody of Mr. Wilson than the former Commander in Chief.

One of the most important, if you’re a fan of the show, things about the episode is the introduction of Disco Stu. And the rest is history.

#37: The Springfield Connection

Original Air Date: May 7, 1995

PLOT: Bored with her life as a housewife, Marge takes a job as a police officer.

Marge episodes are rare, but when they exist, they’re usually high on emotion, low on laughs. But in this episode, we get the opposite, thanks a lot to the supporting cast that makes her attempt to be an officer all the more enjoyable.

What’s great about this episode is that it does give Marge a lot to do. More often than not, its Homer that has a new career path for 22 minutes, but its really nice to see Marge out of her element; and succeed at it as well. This gives us some great interactions between her and Chief Wiggum and in her training montage, he has a few great one-liners: “Women always have trouble with the wall… They can never seem to find the door.”

My favorite part of the episode is the final card game scene when Homer uncovers the counterfeit jeans operation in his “car hole”. The silliness of having the big evil be a counterfeit jeans operation is classic Simpsons. Not to mention the fact that the police force somehow misplaces all the jeans.

#36: Brother From Another Series

Original Air Date: February 23, 1997

PLOT: Sideshow Bob is let out of prison, into the care of his brother Cecil (David Hyde Pierce).

It’s amazing that this episode just turned 16 years old. It really speaks to the, for better or worse, longevity of the show. This is a season eight episode, which means its towards the tail-end of what would be called by most, the best years of the series. Make no mistake though, the show, in hindsight, was still churning out absolute classics seemingly every week. A lot of the future spots on this list will be filled by Season Eight episodes.

In a brilliant, if a little obvious, piece of stunt-casting, David Hyde-Pierce is brought in to play Cecil, Sideshow Bob’s brother. Eight seasons in, its a bit brazen to add to or change the mythos of an already classic character. For example, Season Nine’s episode “The Principal and the Pauper” introduced the Armin Tanzarian-Seymour Skinner plotline that everyone basically agrees sucks. This is Sideshow Bob’s sixth appearance and it is one of my favorites. What makes this show great is what made the show Frasier so great: the chemistry between David Hyde-Pierce and Kelsey Grammer. I can only imagine it was a walk in the park for both of these actors.

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