OK, so this was a nearly impossible task since we keep the lists short and sweet around here and don't usually touch on things as big as "best" but I felt I was up to the challenge. Naturally, taking one of the most popular shows of all time, with a body of over 300 episodes to choose from is a massive undertaking so I had to do a LOT of preparation for this to ensure I wouldn't be looking at this list in the future and saying "damn, I forgot about that one" or "that one really shouldn't be there."
Also naturally, everyone is going to have their own opinion on this one. Luckily, my opinion is the only one that matters.
Deciding what constitutes a "best episode" is also pretty difficult. I found that many of my absolute favourite moments from the show do not in fact take place in episodes I would deem to be among the best. At least not top five best anyway. My main criteria was that the episode had to be great from start to finish with absolutely no lulls and the plot had to be of the very highest quality. There are many Simpsons episodes that make the best of what I would consider to be a weak plot, rising above it with good dialogue or one or two extremely memorable jokes. The episodes listed here all have what I consider to be the very best storylines.
Don't come whining to me saying "what about this episode or that episode?" - this is only a top FIVE for god's sake, there's lots I wish I could have included. I did actually give this one some thought. Dispute me at your own peril.
5. "Homer At The Bat" (season three)
One of the only episodes that heavily relies on celebrity appearances and actually works. While there have been lots of fun celeb cameos on this show, I feel the best ones are those in which it isn't central to the plot. I much prefer stuff like Robert Goulet arriving to play at Mr. Burns' Casino (and subsequently performing at Bart's) to say, Mel Gibson and Homer making a movie together (lame). But this one is my big exception.
The inclusion of nine Major League Baseball players is what the entire episode revolves around. And it's great. From Steve Sax's "runnin' with the law" to Ken Griffey Jr.'s obsession with brain and nerve tonic (which eventually gives him gigantism), this episode is masterfully done. A big reason is it's a great example of Burns' infamous desire to get his own way coupled with his complete lack of knowledge of the world around him (he at first attempts to assemble a softball team made up of long deceased players). His personal battle with Don Mattengly over the latter's alleged sideburns is only outdone by Homer's rivalry with douchebag Darryl Strawberry (who takes to sucking up to Burns and calling him "Skip").
But even with all these professionals present, in the end, it's Homer who emerges as the hero (in typical Homeric fashion) to win the plant the championship. The softball song over the end credits is the icing on the cake.
4. "Bart of Darkness" (season six)
The Simpsons get a pool and Bart breaks his leg. Doesn't sound too special, really. But this episode has a lot going for it. The children of Springfield are nicely featured from Nelson to SherriandTerri to Martin. And while the title is obviously a take on "Heart of Darkness", this episode is really based on the classic Rear Window. Many shows would parody this movie but it's best done here. Jimmy Stewart's character is even included ("Oh no! That sinister looking kid is coming to kill me!"). But we also get a fun look at Bart as he descends into a form of madness before his paranoia regarding Flanders' missing wife surfaces. He writes an amusing English play and plays strange role playing games with boardgame pieces in the dark. And that's only the stuff we know about.
But what I really love about this episode is the little slice of Krusty we get. If The Krusty The Klown Show was a real show, I would watch it all the time. In this particular episode, we are treated to a rare look at "Klassic Krusty" where in the early sixties, shown in glorious black and white we see a suit-clad Krusty discussing collective bargaining agreements. Later, his musical guest is famed Indian musician Ravi Shankar. I just love the idea that Krusty has pretty much always been on TV and that his show always reflected the time period.
We also get to see Springfield's finest using their resources to protect the city - in this case, using a police helicopter to spy on skinnydipping Homer and Marge.
And, like many of the best episodes, there's a great ending. This one with Martin standing naked and alone, surrounded by the ruins of his shattered dream (to be "Queen of Summertime." No, king!) singing "Summer Wind" as the sun slowly begins to set.
3. "You Only Move Twice" (season eight)
Usually, what makes a strong episode for me is a great representation of the city of Springfield and the many colourful characters that inhabit it. That's what makes the show great. Because it's not only the Simpsons who are entertaining characters. There's Principal Skinner and Moe and Snake and Lionel Hutz and Mayor Quimby etc. etc. etc. Needless to say, any episodes that use the formula "the Simpsons go to x", is not popular with me. I always much prefer to see them in their natural environment. But I do have two exceptions to this - "The City of New York vs Homer Simpson" (not included on this list) and "You Only Move Twice", where the family temporarily relocates to planned community Cypress Creek, with Homer accepting what turns out to be a dream job.
What makes up for us not getting to see Springfield and the things we love about it is the introduction of Hank Scorpio, Homer's new boss, who is, simply put, amazing. Here's a guy who from all appearances is the complete opposite of Mr. Burns. He's friendly and personable and in touch with the world around him. He's approachable and informal. And he honestly values Homer as an employee. But it turns out he ALSO is a supervillain, perhaps even more effective than Burns. Where Burns is happy to exploit his employees and grow fat off the status quo, Scorpio treats his employees fairly and truly appreciates their efforts. And the status quo isn't good enough for him, he seeks to gain even more power. In the first "reveal" of this side of his character, we get a brilliant scene where he goes from happily taking the time to inform new employee Homer of where he can acquire some "business hammocks" to aggressively negotiating a ransom with the UN, blowing up the 53rd Street Bridge during the exchange to "prove he isn't bluffing". He gravely announces they have 72 hours to deliver the gold then......"Back to the hammocks, my friend!" Genius.
This is a rare episode where a new character truly steals the show. The actions of Marge, Bart and Lisa are uninteresting by comparison but they do serve the function of eventually triggering Homer to reluctantly give up his new job - quitting during a Bond movie-style invasion of the complex - to go back to his old life (although he does receive the Denver Broncos as a parting gift from his former boss). Which is for the best, after all. We all know the Simpsons belong in Springfield. But we also live in hope that we will one day hear from Hank Scorpio again.
2. "Who Shot Mr. Burns? part 2" (season seven)
The conclusion to the only cliffhanger in Simpsons history, this episode is great right off the hop. Everyone was aware of the obvious similarities to the infamous "Who shot J.R.?" storyline from the drama Dallas, and this episode took it a step further. It begins with Smithers experiencing the "it was all a dream" sequence. Except as it turns out, it wasn't.
What makes this episode stronger than part one is the police investigation. We get Willy's interrogation a la Basic Instinct ("Videogame??") plus Moe's hilarious lie detector test. Principal Skinner bores the cops to tears before finally telling them what they need to know (which naturally includes another embarrassing interaction with Superintendent Chalmers) and ridiculously random guest star Tito Puente entertains with a delightful sizzling samba (his own unique revenge on Burns) There's also a rare appearance from Dr. Colossus which is not to be missed.
Homer's arrest is suspenseful (for The Simpsons, I mean) and the eventual solution to the mystery is clever and satisfying right down to the final shot of Maggie's eyes, leaving us all to wonder if it really was an accident after all.
1. "Radioactive Man" (season seven)
This one actually came out directly after "Who Shot Mr. Burns? part two". And I'll tell you right now - best season of The Simpsons? Season Seven, hands down.
So here we have a movie being filmed in Springfield. And not just any movie. What's interesting is that this episode came out a few years before comic superhero movies would make their big Hollywood comeback (thanks to Marvel).
There's nothing to not like about this episode. Unlike almost any other, I watch it EVERY SINGLE TIME i notice it's on. I've seen it so many times I could probably recite every line. But I'll spare you here. From Comic Book Guy's initial inquiry into who will be the star, we get some great foreshadowing of the way the world is today - with every single movie that comes out, the public already knows pretty much everything about it months before its release thanks to the Internet.
The reference to the "campy seventies" Radioactive Man television series is a simply beautiful sendup of the old "Batman" show. We get a glorious fight scene ("MINT!) with the dastardly villain, The Scoutmaster ("Don't be afraid to use your nails, boys!") culminating in a groovy dance complete with hot go-go dancers. Somewhere, you knew Adam West was laughing his ass off.
We have a great collision of worlds going on here. This time it's Hollywood meets small town America - Springfield. The townspeople race to exploit the movie and its crew in every way they can while the local children scramble to try to be in the movie. Milhouse is granted the honour of being cast as sidekick Fallout Boy (much to Bart's initial chagrin) and his work on the movie is wonderfully funny.
Ranier Wolfcastle is in the starring role and doesn't disappoint. From his delivery of lines ("Up and at them!!!") to his stunt work ("The goggles do nothing!!!"), we see Wolfy at his very best.
Homer lounges with teamsters while the kids learn the magic of moviemaking (like painting horses to look like cows). Mayor Quimby passes every tax he can think of to squeeze dough out of the film crew and Milhouse struggles with the reality of being an actor. Eventually cracking under the pressure, he takes off. Not even being swayed by Biggest Star in the World, Mickey Rooney, he forces production to shut down as the producers are all broke by that time anyway.
The scene depicting the film makers' attempt to finish the movie without Milhouse by editing together existing footage of him is one of the funniest things I've ever seen. The ending showing the bankrupt film crew being embraced by their Hollywood brethren upon their return to Tinsil Town, complete with "Lean on Me" playing, makes for a great conclusion in all its joyous satire. In the end, the Radioactive Man movie was just too awesome to ever be made.