"The Simpsons" aired its 23rd season finale on May 20 in an episode titled "Lisa Goes Gaga" (guest-starring Lady Gaga). Yet as much as any true fan hates to admit it, the series hit its comedy peak years ago. The real debate lies in what season that peak took place, usually ranging anywhere from Season 4 to Season 12. So for the sake of this piece, let’s consider Season 12 to be the end of the “classic Simpsons era." What made those early seasons so endearing, so near perfect in terms of quality and hilarity is really based on the individual, but surely most will attribute it to their sharp wit and that sentimental Simpsons heart that, sadly, has lost a bit of its touch over the years due to overuse and retreading. Be that as it may, every so often there comes an episode that shows you not only why you fell in love with these characters in the first place, but would also serve as a fitting swan song for America's favorite cartoon family. Let’s take a look at eight of the best, and reflect on what made them series-finale-worthy.
No. 8 - “Boy Meets Curl” (Season 21, Episode 12)
While there may not be anything particularly conclusive in this episode in terms of where the Simpson family goes from here, it does show that the sky is the limit in terms of what they are capable of (competing in the Winter Olympic Games in this case). It also contains some of the funnier gags in recent seasons, like a brief but memorable appearance from the Medicine Woman (aka “Boob Lady” from "The Simpsons Movie"), as well as the light, heartfelt sentiment we’ve grown to appreciate from the series. And for a show that has run as long as "The Simpsons" has, could we ask for anything more from a final outing?
No. 7 - “Homer Scissorhands” (Season 22, Episode 20)
While the main story revolves around yet another hidden talent of one Homer J. Simpson, the real pleasure that comes from this episode and makes it a worthy finale contender is the kiss between Lisa and Milhouse. This is a pairing that was years in the making, so it’s a treat for long time fans to see it come to fruition, if only for an episode. Even executive producer Al Jean has been quoted as saying, “If [Lisa] winds up with anybody, it's going to be Milhouse. In my heart, I think they'll be together.”
While Homer discovering he is a natural barber due to growing up longing for hair of his own may seem a little cliche or repetitive by now, the story actually ends on a very sweet note, with Homer quitting his career as a hair stylist and reserving his special skill for his one and only, Marge.
No. 6 - “Poppa's Got a Brand New Badge" (Season 13, Episode 22)
Nostalgia goes a long way in ending a series’ run, and there is no easier way to achieve it than having Homer rattle off all the occupations he has filled in the past 13 years. Couple that with a compelling storyline, clever jokes and satire (i.e. using a cinder block to break into a cinder-block store, Jimbo shopping at the Wooly Bully, "The Sopranos" parody) and an ending that alludes to the possibility that Maggie shooting Mr. Burns seasons ago may not have been so innocent, and you have an episode of "The Simpsons" that ranks right up there with any one of the classics. Plus, with it being just out of that “classic era” range itself, it has just enough of the old juices left in it to send the series out on a high note.
No. 5 - “Old Yeller-Belly" (Season 14, Episode 19)
What better place to start an ending than by going back to the beginning? When Santa’s Little Helper is branded a coward and disowned by Homer after failing to save him from a fire, he ends up back in the arms of his original owner who left him at the dog track way back in “Simpsons Roasting on an Open Fire." And, in true Simpsons fashion, it is left up to Homer (in another one of his harebrained schemes) to get him back. If that doesn’t scream series finale, what does?
No. 4 - “Thank God, It’s Doomsday” (Season 16, Episode 19)
For a show that has been everywhere and done everything, an argument could easily be made that the apocalypse is the only thing left to do. That is exactly what you get in this episode. After Homer sees a movie about the rapture titled “Left Below” (which stands alone as one of the funniest, most-pointed faux movies the show has ever done), he begins to see signs of doomsday all over Springfield and figures out that Judgment Day is upon them. However, once the town labels him a crackpot and he is raptured alone, he defies God himself to ensure his family’s safety. Not even Armageddon can stop "The Simpsons."
No. 3 - “A Totally Fun Thing Bart Will Never Do Again" (Season 23, Episode 19)
In addition to crossing the Simpsons’ seventh and final continent, Antarctica, off of their to-do list, it is the moral of this story that truly feels like goodbye for such a fantastic series. The final shot of Bart as an elderly man passing away with a smile on his face having realized that he made the most of the best times in his life not only says something about how one should try to live, but would also serve as a great metaphor for the series itself and “what a great ride” it has been ("What a great ride" is the last line in the episode).
No. 2 - “Eternal Moonshine of the Simpson Mind” (Season 19, Episode 9)
An episode that previously mentioned Al Jean regards as one of two that would have served as an adequate series finale (the other being Season 12’s “Behind the Laughter”), this episode contains everything that makes "The Simpsons" great. From its engrossing, movie-inspired plot to its ending, this tale of forgotten memories and the journey taken to recover them has it all. Watching Homer and Marge kiss as they sail off into the moonlight with virtually everyone else in Springfield quite frankly feels like "The End," and one would be hard pressed to think of a more perfect way to say farewell to the series. Perhaps that's why the writers included the question mark on the boat.
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No. 1 - “Springfield Up” (Season 18, Episode 13)
Presented in documentary style, “Springfield Up” would make a fine send-off for not only the Simpson family, but for Springfield itself, as it focuses on several key townspeople in addition to Homer and Marge over a period of 32 years. And though too much focus on a small side character can often ruin what makes them appealing, this episode pulls it off nicely, with the origin of Eleanor Abernathy (the Crazy Cat Lady) being a standout. Having guest star Eric Idle voice the snooty documentary filmmaker Declan Desmond doesn’t hurt the episode's cause either, and may in fact be the icing on the cake.
It is an interesting episode concept in itself with a very touching ending, and feels like a warm, fun and complete way to say goodbye to such a diverse group of lovable characters. That's why it is No. 1 on this list.