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The Best Episodes Of The Simpsons, According To IMDb

When it comes to beloved, long-running animated series, it can be difficult to narrow down the best handful of episodes — and in the case of The Simpsons in particular, the task looks next to impossible. "Long-running" doesn't quite cover it; the show has been on the air longer than many of you reading this have been alive, spanning 31 seasons and an unbelievable 679 episodes as of this writing. The Simpsons is by far the longest-running prime time scripted television series in history; for perspective, the next-longest running, Law & Order: Special Victims Unit, boasts "only" 21 seasons and 476 episodes.

The venerable website IMDB uses the votes of its registered users to rank pretty much every television episode ever made, and its top five episodes of The Simpsons shouldn't shock you in one respect: none of them were produced any later than season 8, after which it's generally agreed that the show became rather hit-and-miss. You may be surprised, though, to see which episodes are missing — but do keep in mind that with nearly 700 episodes in its library, any top five ranking will necessarily exclude some stone cold classics.

For example, here are just a few of the brilliant episodes that didn't make that cut, but can be found elsewhere in the top 20: season 4's "Mr. Plow"; season 7's "King-Size Homer"; the amazing, bizarre season 7 anthology "22 Short Films About Springfield"; season 5's "Deep Space Homer"; and from season 4, "Marge vs. the Monorail," which is often cited as being among the greatest episodes of television comedy ever produced.

With episodes like those on the outside looking in, which Simpsons installments were voted as the absolute best by IMDb's users? We're glad you asked.

Season 5, Episode 2: "Cape Feare"

Pretty much very episode to ever feature Bart's deadly nemesis Sideshow Bob (Kelsey Grammer) is a classic, but season 5's "Cape Feare" is special. A parody of the 1962 noir classic Cape Fear and its 1991 Martin Scorsese-directed remake, the episode sees the Simpsons entering the Witness Protection Program when Bob, who is plainly and unapologetically still obsessed with killing Bart, is released from prison. Taking on the surname Thompson (a brilliant gag involves a cop trying futilely to drill Homer's new name into his thick head), the family relocates to scenic Terror Lake, with Bob tagging along under their car.

Bob manages to corner Bart alone aboard the family's riverboat, but Bart — noticing that on its current course, the boat will soon arrive in Springfield — comes up with an amazing final request. He asks Bob to perform the score of the Gilbert and Sullivan opera H.M.S. Pinafore in its entirety, stalling him just long enough for the lazy river to deliver him into the waiting arms of the Springfield police.

The episode contains far too many classic gags to discuss here, but here's an interesting tidbit: the show's writers had difficulty stretching it out to a full 22 minutes. They remedied the situation by recycling an older couch gag (the longest in the show's history) and extending a bit of physical comedy wherein Sideshow Bob steps on a rake, sending the poor guy through a seemingly endless gauntlet of rakes. The gag would be referenced frequently throughout the show's history, such as in the season 12 episode "Day of the Jackanapes," in which Bob steps on a rake before uttering, "Rakes... my old arch-enemy."

Season 6, Episode 6: "Treehouse of Horror V"

Many a Simpsons fan would make the case that pretty much every "Treehouse of Horror" Halloween episode is among the best ever, but IMDb users singled out one in particular: "Treehouse of Horror V," which aired during the sixth season. The episode's second and third segments are certainly awesome: in "Time and Punishment," Homer's toaster becomes a time machine, enabling him to make repeated sojourns into the past which screw mightily with the present; and in "Nightmare Cafteria," the staff of Springfield Elementary decide to cut corners on food costs by eating the students. But it's the first segment, "The Shinning," that really, er, shines.

The segment is, of course, a spoof of Stephen King's novel The Shining and Stanley Kubrick's film adaptation (but as Groundskeeper Willie points out, Bart shouldn't refer to his psychic ability as such, lest they all get sued). In it, the Simpson family are to take care of Mr. Burns' lodge for the winter, but Homer predictably goes all Jack Torrance on his family — not due to malevolent ghosts, but because of the lack of TV and beer.

In the segment's most inspired gag, Homer — being interrogated as to his mental state by Marge — isn't sure what he's just finished scrawling all over the walls ("No TV and no beer make Homer go crazy," a reference to the single sentence Torrance fills hundreds of pages with in the movie). He forgets the last two words, causing Marge to prompt him, "...go crazy?" To which Homer screams in response, "DON'T MIND IF I DO!"

"Treehouse of Horror V" is one of the darkest, bloodiest Simpsons Halloween episodes ever (Willie, for instance, is murdered with an axe in every single segment), but it should come as no surprise that it's also one of the funniest.

Season 6, Episode 25: "Who Shot Mr. Burns? Part One"

The Simpsons season 6 concluded with the first part of the two-part episode, "Who Shot Mr. Burns?" which was modeled in part on the cliffhanger of the season 3 finale of the primetime soap opera Dallas (which had all of America wondering "Who shot J.R.?" for the better part of a year). The second part is, of course, also great (IMDb ranks it eleventh all-time), but part one is brilliant for how it deliberately sets up the central crime, dropping clues all all the while, as the megalomaniac Mr. Burns methodically goes about pissing off literally everybody in Springfield.

It all begins when Burns uses slant drilling to siphon off a rich oil deposit recently discovered underneath Springfield Elementary, causing a domino effect which bankrupts the school, shuts down Moe's Tavern, and destroys the Springfield Retirement Castle. Having secured a virtual energy monopoly in the town, Burns unveils his master plan: to construct a giant disc that will block out the Sun, leaving all of Springfield totally dependent on him. 

On top of these dastardly deeds, he enrages Homer by constantly forgetting his name, destroys Bart's treehouse (which even injures poor Santa's Little Helper), and even fires Smithers. The episode concludes with Burns activating his sun blocker at a town hall meeting, before exiting through an alley to be shot by... parties unknown. He then collapses on the town sundial, with his position giving a strong clue as to who his assailant was. We won't spoil the solution of the 25-year old mystery, but we will say that despite Burns' assertion early in the episode, taking candy from a baby isn't always as easy as one might think.

Season 8, Episode 2: "You Only Move Twice"

The season 8 episode "You Only Move Twice" is notable for featuring one of the only other times the Simpsons have departed Springfield (with no Witness Protection Program involved this time), and for featuring one of the most memorable supporting characters in the show's history: Hank Scorpio, Homer's new boss at the Globex Corporation. Upon scoring his new gig, Homer convinces the family to move to the (much) nicer town of Cypress Creek. Unfortunately, virtually nothing about the town is as it seems — including Scorpio.

One by one, the Simpsons become severely disenchanted with their new town: Bart finds himself in a remedial class at his new school; Lisa finds that the town's pristine nature preserves are of no use to her, since she's allergic to all the wildlife; and the family's new self-cleaning home leaves Marge bored (and drunk) out of her skull. Oh, and while he's a great boss who listens with interest to Homer's dream of one day owning the Dallas Cowboys, it turns out that Scorpio is a full-on James Bond villain (sorry, that's James Bont) with designs on seizing control of the entire East Coast.

"You Only Move Twice" is chock full of inspired gags, not the least of which is the one which closes the episode. After Homer dejectedly moves the family back home, he's disappointed to find that Scorpio has sent him a parting gift: the Denver Broncos, which are depicted as a team of bumbling oafs. Okay, so the gag didn't age terribly well; just over a year after the episode's airing, the Broncos finally won their first championship, a 31-24 victory over Green Bay in Super Bowl XXXII.

Season 8, Episode 23: "Homer's Enemy"

The Simpsons episode voted the best ever by IMDb's users is also, without question, the absolute darkest installment of the whole series: season 8's "Homer's Enemy," in which a new hire at the Springfield Nuclear Power Plant, Frank Grimes (voiced by Hank Azaria) strikes up a vendetta against Homer that ends... poorly for him. A level-headed, sensible man, Grimes (or "Grimey," as Homer calls him to his endless annoyance) becomes increasingly enraged over the fact that Homer is well-liked and lives a comfortable life, despite his obvious and flagrant incompetence. Grimes declares himself to be Homer's enemy — but of course, his every attempt to cut the buffoon down to size backfires terribly.

This culminates in a classic sequence late in the third act, in which Grimes — halfway out of his mind with rage and exasperation — goes nuts in the power plant, mimicking and brutally mocking Homer's typical behavior. ("I can be lazy too!" he screams at some random employees while mooning them. "Look at me! I'm a worthless employee, just like Homer Simpson! Give me a promotion!") His rampage goes on for several minutes while his co-workers look on in confusion, until finally, he happens across a set of high voltage wires. "What's this? Extremely high voltage," he says. "Well, I don't need safety gloves, because I'm Homer Simp-" He grabs the wires with his bare hands, there's a crackling sound — and we smash cut to Grimes' grave.

Yep, that's right — the whole town is at Grimes' funeral, including Homer, who falls asleep as Reverend Lovejoy eulogizes "Frank Grimes, or Grimey, as he liked to be called." It's a jaw-dropping conclusion to an episode that reminds us that, at its best, The Simpsons could be mercilessly funny — not to mention just plain merciless.