The Simpsons series has over 500 episodes, more than any other television series in history, which makes distilling them to the eight best a nearly impossible task. The following list is in no particular order and in no way definitive. There is something to love in every Simpsons episode, but these are simply the ones that brought out the best of the yellow family and worst of society in hilarious ways.
The first of the best is the original Treehouse of Horror that aired during the second season with James Earl Jones lending a guest voice. This episode launched a yearly Halloween event in the Simpson universe that offered three stories in a single half hour. Bad Dream House immediately set a darker tone for cartoons in general, while Hungry Are The Damned introduced series main-stays Kang and Kodos. The entire experience was punctuated by a haunting reading of The Raven by James Earl Jones with Bart playing the winged fiend. Full of memorable quotes and culture references, this primeval special scared shorts off kids and adults and continues to inspire today.
Jumping ahead about 23 seasons, there is the episode Brick Like Me that crossed over Springfield with Lego figures. This tale of immortal sameness versus reality taught the brain-damaged Homer to be a better father outside the Lego set. Numerous businesses received Lego-based names such as H & R Brick and Brick-E-Mart, and each character was given a place in a storyline ripe with aware parody. Few other shows can accomplish the level of humor reached when this writing staff has crossover on mind, and the spun tale here is among their most humorous.
Another example of Simpson crossover fun is The Springfield Files where David Duchovny and Gillian Anderson reprise their X-Files roles. Probably the most masterful example of crossover fun, there are so many small chuckles that build up to heftier laughs in the middle of the episode. Almost every field of science-fiction, from video games to flopping Kevin Costner movies, makes an appearance, including Leonard Nimoy and the classic music from Psycho. No other partnership has lent so completely to the Springfield formula, leaving this episode as the bar for future crossovers to hit.
When talking about the best Simpsons episodes, at least one in the top eight will have something to do with their show within the show: Itchy & Scratchy. The episode where their movie came to the big screen worked on many levels as a parody of blockbuster movies in general, and the real-life Simpsons movie that would come almost 15 years later. Within the episode, Bart has to deal with punishment from Homer for the first time, winding up as the Chief Justice of the Supreme Court by missing “our generation’s moon landing,” as Lisa says. Homer, in his dedication, offers a rare glimpse at his clever side as he thinks two steps ahead of Bart at every turn, which helps deliver a hilarious arc from beginning to 40 years in the future.
22 Short Films About Springfield takes the spotlight away from the core quintet in favor of the ever-expanding cast of side characters. Comprised to represent Pulp Fiction, the stories weave in and out of one another, with different scenarios giving personality to those characters that usually did not see much screen time without a Simpson family member around. Homer still finds a way to put Maggie in danger, but characters such as Principal Skinner, Milhouse, and Chief Wiggum garner a majority of the attention. This represented the depth of story content in this universe that led to some fairly entertaining focuses on these characters and others in future episodes.
Treehouse of Horror Six is another creepy amalgamation of stories that broke yet another mold for television and comedy. Giant advertising monsters level Springfield in the first arc, thanks to Homer taking a huge, metallic donut, and only went away when people stopped paying them any attention. Possibly the most influential Simpsons episode on other animators, Homer Cubed showed the world what three-dimensional animation could do in cutting-edge fashion. There are reasons this section itself won several awards for visual and comedic achievement, as three-dimensional takes on entertainment simply were not around yet in 1996.
I’m Goin’ to Praise Land is often an underrated episode that is lost in the vast library of classics. The series has dealt with death to some characters, but very few changed anything for the stories beyond an episode or two. When Maude Flanders died, Ned underwent a substantial change from “neighborino” to a sympathetic figure searching for something to fill that hole. This episode put him on that path by building a theme park in her honor, showing flexibility that no other animated show can tout and giving Ned a completely new direction that continues to this day.
Rounding out the eight best Simpsons episodes is one of the few that take a look into the future. Future-Drama flipped the script on the one-off period pieces the show was fond of doing every so often. The glimpse into the future of Bart and Lisa here was actually fit into canon for future episodes, turning these scenarios from fiction within fiction to reality for the Simpson family. Marge and Homer rediscover love, Maggie goes to an Alaskan beach and a hover car that doesn’t quite hover run the gamete of comedy and familial love for their not-too-distant futures in this episode. This, along with subsequent glimpses forward, created a new storyline for Simpsons fans to love, even if Maggie is still not allowed to talk.
Opinion by Myles Gann