Will The Simpsons end its long and illustrious run with a truncated final run after 26 seasons? Anything is technically possible, but its infinitely more likely that the matter will be amicably resolved and a full season 27 will be delivered to the fans. With that said, though, at some point, the show’s producers will have a hell of a challenge to deal with: how do you live up to almost 600 episodes of television and the iconic and awesome legacy of everything that The Simpsons has accomplished while also exiting in a way that somehow feels right? No one is prepared for that moment, but interestingly enough, the writers have inadvertently created a handful of episodes of The Simpsons that could have, in hindsight, worked as series finales and an apt departure point. So with that said, here are those episodes.
“Summer Of 4 ft. 2” — Original Air Date: May 19, 1996
After realizing just how unpopular she is, Lisa strives to change herself while the family stays at the Flanders’ beach house. She quickly fits in with a bunch of surfer-type kids mostly by pretending to be like them and abandoning her nerdy personality. But while Lisa isn’t being totally honest with herself here, we can still understand why she makes these drastic changes to her personality, and also feel awful for her when Bart attempts to sabotage her friendship by telling her new friends about her goody-two-shows past. Thankfully, Lisa’s new friends embrace her for who she is, and give her a going away present that Homer can’t exactly appreciate (“Sweet merciful crap! My car!”), but which makes Lisa feel like she finally has real friends. Had the series ended here, poor Lisa’s story would have ended on a decidedly happy note.
“Homer’s Enemy” — Original Air Date: May 4, 1997
A decidedly meta episode, “Homer’s Enemy” essentially looked at what would happen if a normal person had to deal with Homer Simpson’s antics. Naturally, poor Frank Grimes was appalled by Homer, who ratcheted things up for this episode. This is undoubtedly a brilliant piece of television, but one can’t help but wonder if it was also a tacit admission by the writers that they had done all they could with Homer Simpson. That he would eventually devolve from a human being into a wacky ball of outrageousness in subsequent seasons would only support this theory. Had The Simpsons stopped at “Homer’s Enemy,” we would have been spared those changes to Homer’s character. Then again, we also would have lost great post-classic era episodes like “Trilogy Of Error,” and “Thirty Minutes Over Tokyo,” so it’s a bit of a tough call.