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The 50 Best "Simpsons" Episodes Of All Time

With the show's 500th episode airing this Sunday, we take a look back at the animated Springfield family's best efforts.

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Since its debut in 1989, The Simpsons has revolutionized the way the world views animated shows. Taking cartoons out of their Saturday morning rut, the long-running Fox hit brings sophisticated plots, intelligent humor, and memorable characters into our living rooms every week. And throughout its history, creator Matt Groening's landmark series has racked up more awards and accolades than almost any other television show in history.

Each new Simpsons episode is filled with quotable lines and phrases that have become part of the American lexicon over the years, and seemingly everybody has their own opinions on which one is the best. But for a show that has been on for 23 seasons, picking one favorite episode is almost impossible.

This Sunday marks the latest milestone for America’s favorite family as The Simpsons will air its 500th episode, which will debut on Fox at 8pm EST. To celebrate this occasion, we’re taking a look back at The 50 Best Simpsons Episodes Of All Time.

RELATED: The 20 Best Simpsons Quotes You Can Use

Written by Jason Serafino (@Serafinoj1)

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The Joy of Sect

50. "The Joy Of Sect" (February 8, 1998)

Admittedly, the late ‘90s didn’t quite capture the quality of the show’s early days, yet "The Joy of Sect" stands out as a great episode in an otherwise disappointing ninth season. After Springfield is overrun by a mysterious cult, the Simpson family—Homer, in particular—get brainwashed by the group’s empty promises. By the end, it’s up to Marge to free her family and expose this cult for what it truly is.

Even though the episode might not send direct shots at any religion in particular, The Simpsons again takes aim at any group that forces its members to give up their freewill. Of course, they do it all with a touch of humor that should make even the most ardent churchgoer smile.

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Bart's Comet

49. "Bart’s Comet" (February 5, 1995)

When Bart accidentally discovers a comet hurtling towards Springfield, the town falls into a panic once they realize that they are woefully underprepared for, well, anything. Though it's a little hard to buy at times, "Bart's Comet" provides enough laughs that audiences should find it easy to suspend their disbelief, if only for a moment.

Written by the brilliant John Swartzwelder (who has written 59 episodes to date), "Bart’s Comet" is full of the nihilistic humor that we have grown accustomed to over the years, and it ends on a sweet note that's highly satisfying.

Sideshow Bob Roberts

48. "Sideshow Bob Roberts" (October 9, 1994)

Almost every season of The Simpsons has featured a Sideshow Bob episode that focuses on him trying to get revenge on Bart for sending him to prison all the way back in season one. In "Sideshow Bob Roberts", Bob gets himself elected mayor of Springfield to make the family's lives a living hell.

Filled with parodies and allusions to All The President’s Men, Citizen Kane, Rush Limbaugh, and a whole host of other political subject matter, the half-hour ep is a smart attack on a corrupt political system that doesn’t sacrifice content for jokes. Also, the fact that Nosferatu is a member of Springfield's Republican Party in this episode is just too brilliant to go unmentioned.

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Simpsons Roasting On An Open Fire

47. "Simpsons Roasting On An Open Fire" (December 17, 1989)

Here's the one that started it all. "Simpsons Roasting On An Open Fire" is the debut full-length episode of The Simpsons that transformed the show from crude shorts on The Tracy Ullman Show to becoming a full-fledged pop-culture phenomenon. And, most importantly, it’s also incredibly funny.

"Simpsons Roasting On An Open Fire" sets the stage beautifully for the series' future by combining crass humor and believable family moments into one groundbreaking package. This kind of storytelling simply wasn’t seen in animation at the time. Best of all, it's a Christmas-themed episode that plays well any day of the year.

Two Bad Neighbors

46. "Two Bad Neighbors" (January 14, 1996)

Let’s face it: Who hasn’t wanted to punch George Bush in the head at some point in their life? Well, in "Two Bad Neighbors," Homer doesn’t just get to punch the former President—he gets to unleash a swarm of locusts on him as well.

When Bush moves across the street from the Simpsons, he runs afoul of the family after he spanks Bart for ruining his memoirs. This leads to a series of increasingly obnoxious pranks that both sides pull that culminates in a fist-fight in the sewers. It would have been nice for Bush to voice himself in the show; Harry Shearer’s impression, however, is still pretty spot-on.

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War Of The Simpsons

45. "War Of The Simpsons" (May 2, 1991)

There have been plenty of episodes that focus on Homer and Marge’s rocky marriage during the years; "War Of The Simpsons" ranks among the best because it played everything out so realistically. After a huge blow-out at a party, Marge suggests that she and Homer to a marriage counselor, and although Homer agrees, his only motivation to go on the retreat is so he can go fishing.

This leads to a fight so fierce and authentic that it seemed like the only way to solve the problem was through divorce. But by the end, Homer more than makes things right, and "War Of The Simpsons" provided audiences with the first really great emotional episode during the series’ second season.

Rosebud

44. "Rosebud" (October 21, 1993)

One thing that The Simpsons revolutionized was the art of the movie parody, and in "Rosebud," America’s most famous yellow family took on one of the greatest films in American history: Citizen Kane.

Portraying Mr. Burns as a Charles Foster Kane-esque millionaire in search of his lost childhood innocence (in the form of his childhood teddy bear “Bobo”), this episode blisters along with an endless supply of memorable jokes and moments, such as a classic cameo by The Ramones.

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Bart The Lover

43. "Bart The Lover" (February 13, 1992)

One of the most despicable, yet endearing, characters in Springfield is Edna Krabappel, the jaded and lustful, fourth grade teacher. In "Bart The Lover," she's divorced, miserable, and turns to the personal ads to score a man. Little does she know, though, that the man she was sending salacious pictures to through the mail was actually Bart using a pseudonym.

The ensuing series of events almost makes you feel guilty for laughing, but they’re just too funny to pass up. The fact that an entire episode could be kept afloat by a middle-aged, man-hungry elementary school teacher is just another reason why The Simpsons has quite possibly the best supporting cast in the history of television.

Mr. Plow

42. "Mr. Plow" (November 19, 1992)

When you can feature both the legendary Phil Hartman and Adam West and have them pale in comparison to another episode highlight, you know you have something special.

"Mr. Plow" revolves around Homer starting a snow plow business in order to earn some extra money, but his best friend Barney beats him to the punch and tries to drive him out of business. What follows is an episode jam-packed with jokes and classic moments, such as Homer’s famous Mr. Plow jingle. In November 1992, The Simpsons was just beginning to hit its stride, and "Mr. Plow" raised the bar for what was to come.

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Bart The Daredevil

41. "Bart The Daredevil" (December 6, 1990)

This episode might be best remembered for Homer’s trips off of Springfield Gorge, but the truth is that "Bart The Daredevil" was the beginning of the Simpsons style that would take the show through the next decade. It’s here that the blend of family drama and wacky humor was at its best, as Homer pleaded with Bart to stop training to become a death-defying daredevil.

"Bart The Daredevil" also features the debut of Captain Lance Murdock, the Evel Knievel-esque daredevil that gets lit on fire, breaks every bone in his body, and winds up getting mauled by a lion all within the episode’s 22-minute duration.

Marge Vs. The Monorail

40. "Marge Vs. The Monorail" (January 14, 1993)

After the town of Springfield gets swindled by a slick-talking monorail builder named Lyle Lanley, the citizens quickly realizes that their new train might not be as safe as Lanley claimed. For a great conductor, the cheap construction would still be tough to overcome; unfortunately, Homer is the man behind the wheel here and it quickly leads to mayhem on the rail.

Written by Conan O’Brien, "Marge Vs. The Monorail" features a classic musical number and sublime voice acting from the late Phil Hartman. And in one of the show's all-time best closing lines, Homer anchors the out-of-control monorail to a gigantic metal donut and simply states, “Donuts, is there anything they can’t do?”

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Secrets Of A Successful Marriage

39. "Secrets Of A Successful Marriage" (May 19, 1994)

Who better to teach an adult education course on marriage than a barely-functioning alcoholic who routinely strangles his son and ignores his wife?

When Homer takes said teaching gig in "Secrets Of a Successful Marriage", he quickly realizes that he's in way over his head. Though, after he gets the class’ attention by revealing some of Marge’s most guarded secrets, he actually gains the respect of his students. And, unfortunately, winds up getting kicked out of the house by his wife in retaliation.

How Marge has put up with Homer for all these years has always been one of the show’s bigger mysteries, and she reaches her boiling point here. Eventually, she sees how filthy and desperate Homer gets when separated from her, and happiness returns.

"Secrets Of A Successful Marriage" is a great examination of what makes their relationship tick, and how utterly dependent Homer is on Marge.

Whacking Day

38. "Whacking Day" (April 29, 1993)

Not many towns would create a holiday based around beating snakes to death with baseball bats, but Springfield isn’t like any other town, a fact evidenced by its escalator to nowhere and popsicle stick skyscraper. This episode does a good job of shining some light on animal cruelty; in addition, "Whacking Day" also features some great jokes and a musical cameo by Barry White.

"Whacking Day" didn’t, however, create the feeling of animal equality that the show’s producers intended; in fact, Australia recently adopted Toad Day Out, where thousands of cane toads are destroyed, which was apparently inspired by "Whacking Day". We think they missed the point a bit.

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Lisa On Ice

37. "Lisa On Ice" (November 14, 1994)

"Lisa On Ice" pits Bart and Lisa against each other on opposing hockey teams, with Homer caught in the middle and ready to shower the winner with love. The sports-themed episode eviscerates those obnoxious mini-athletes' parents who show up to their kid’s games drunk and abusive; however, it also concurrently paints a beautiful portrait of the love between a brother and a sister. We dare you not to get a little misty-eyed when Bart and Lisa embrace on center ice during the closing moments.

Flaming Moe's

36. "Flaming Moe’s" (November 21, 1991)

After Moe the bartender steals Homer’s idea for an intoxicating new drink, he becomes rich and famous while his former friend remains in obscurity. This, unsurprisingly, leads to Homer's jealous rage; he tries to ruin Moe’s business by spilling the beans on the secret recipe to everybody.

Featuring an appropriate parody of Cheers and an appearance by Aerosmith, "Flaming Moe’s" was an early gem for the show that paved the way for much better things in the future.

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When Flanders Failed

35. "When Flanders Failed" (October 3, 1991)

In perhaps the best episode to explore Homer’s irrational hatred for Ned Flanders, "When Flanders Failed" works so well because it begins with Homer as an abject jerk and ends with him redeeming himself in grand fashion.

Homer might impulsively wish for Flanders’ business to fail in this story, but when it actually does, he’s horrified to see the Flanders clan living out of their car and selling off their possessions. It’s a story of guilt and friendship, these themes that often take a backseat to pure, unadulterated laughter.

Homer At The Bat

34. "Homer At The Bat" (February 20, 1992)

In recent Simpsons seasons, there's never an episode that goes by without a cavalcade of unnecessary guest stars clogging up the plots and ruining jokes. "Homer At The Bat," however, proved that you can have celebrities provide voices and still make the episode stand out.

Here, Ken Griffey Jr., Darryl Strawberry, Roger Clemens, Wade Boggs, Mike Scoscia, and a host of other big leaguers take the field for the power plant's softball team and provide some excellent laughs. The best part easily belongs to Don Mattingly, though, who gets kicked off the team for not shaving his sideburns—or whatever Mr. Burns thought sideburns were.

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The Way We Was

33. "The Way We Was" (January 31, 1991)

This flashback episode takes a look back at the day Homer and Marge met in high school. Set in a time when bell-bottoms were hip, sideburns were in, and Homer had hair, "The Way We Was" presents a trip down memory lane that adds so much weight and authenticity to the Simpson marriage.

Featuring solid guest voice work from John Lovitz (as Marge’s prom date, Artie Ziff), "The Way we Was" deals with the same issues that any high school kid is all too familiar with, but it does so with The Simpsons' typically slanted views. Despite being a little sappy, it's the perfect examination of why Marge has put with Homer for all these years.

Deep Space Homer

32. "Deep Space Homer" (February 24, 1994)

"Deep Space Homer" is so completely off-the-wall that it borders on ludicrous; fortunately, it’s also so funny that its craziness doesn’t ruin anything. In "Deep Space Homer," NASA sends Homer into space in an attempt to boost ratings for their shuttle launches.

It's 22 minutes of straight laughs, most notably the scene where Kent Brockman mistakes footage of a swarm of ants inside the shuttle for an invading army of mutated insects. With the famous line, “I, for one, welcome our new insect overlords,” The Simpsons created a cult-classic quote that has been referenced on various websites, books, and even an episode of Jeopardy.

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$pringfield

31. "$pringfield (Or How I Learned To Stop Worrying And Love Legalized Gambling)" (December 16, 1993)

When Mr. Burns constructs a casino in Springfield in order to boost revenue, Homer becomes a blackjack dealer while Marge quickly becomes a full-blown gambling addict. This episode works not just because of the humor—which happens often and always—but because of the references to pop culture and historical figures sprinkled throughout.

Here, we have parodies of The Wizard Of Oz and Rain Man; not to mention, by the end of the episode, Mr. Burns begins to resemble a reclusive Howard Hughes, complete with scraggly beard and bottled urine.

Bart Gets An F

30. "Bart Gets An F" (October 11, 1990)

It’s no secret that Bart will never capture the attention of any Ivy League schools, and for a long time he never seemed to mind. But in "Bart Gets An F," his constant underachieving could potentially result in him getting left back a grade.

Thanks to great writing and fantastic voice acting, Bart’s struggles really hit home. You can see the pain and embarrassment he feels when he sees how much dumber he is than his classmates. Just thinking about gets us a bit choked up.

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Radioactive Man

29. "Radioactive Man" (September 24, 1995)

Before the wave of superhero movies swept through Hollywood in real life, it came to Springfield in full-force when a studio decided to shoot a big-budget Radioactive Man movie in town.

For comic book fans, there's plenty to like here, with The Simpsons taking on modern superheroes as well as the campy ‘60s Batman show. Aside from that, though, the episode's MVP is Rainier Wolfcastle (voiced by Harry Shearer), the guy in Radioactive Man's costume. Wolfcastle's highlight? When a stunt goes terribly wrong and he utters one of the funniest lines in Simpsons history: "My eyes! The goggles do nothing!"

Homer Vs. The Eighteenth Amendment

28. "Homer Vs. The Eighteenth Amendment" (March 16, 1997)

“To alcohol! The cause of, and solution to, all of life’s problems.” When Homer spoke these words in "Homer vs. The Eighteenth Amendment," the statement instantly became a classic Simpsons moment.

It happened at the end of an episode that saw prohibition hit Springfield, forcing Homer to become a rum-runner. And after he dueled wits with an officer from the U.S. Treasury Department named Rex Banner for 22-minutes, fans finally got to see a crafty, entrepreneurial side to Homer that isn't often showcased.

This episode doesn’t demonize alcohol or support prohibition; rather, it speaks to a nation of people that depend on alcohol to be able to deal with their day-to-day lives.

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The Homer They Fall

27. "The Homer They Fall" (November 10, 1996)

Homer has held over 150 different jobs during The Simpsons' entire run to date, yet the most memorable remains his stint as a boxer in "The Homer They Fall."

After it’s discovered that Homer can take an incredible amount of punishment without falling down, Moe convinces him to become a boxer and becomes his manager. This all works beautifully until Homer has to go one-on-one with Drederick Tatum, the Mike Tyson-esque “baddest man on the planet."

The result is a pounding of biblical proportions as Tatum beats Homer senseless, much to our amusement. It's some of the worst physical abuse our man Homer has ever endured.

You Only Move Twice

26. "You Only Move Twice" (November 3, 1996)

"You Only Move Twice" is one of the best examples of how a great guest star can elevate an entire episode to legendary status. Albert Brooks’ performance as Homer’s new boss, Hank Scorpio, isn’t just funny—it’s so magnificent that we wouldn’t mind seeing him as a full-time cast member.

By day, Scorpio runs power plant in Cypress Creek, but by night he is a James Bond style super villian with aspirations for world domination. Watching each member of the family deal with their new home in Cypress Creek is great, but, as usual, it’s Homer’s complete ignorance to his boss’ megalomaniacal behavior that’s the episode's true highlight.

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Hurricane Neddy

25. "Hurricane Neddy" (December 29, 1996)

One of the most successful aspects of The Simpsons throughout the years has been the writers’ ability to focus an episode on an ancillary character and still manage to craft a hilarious story. And "Hurricane Neddy" might be one of the best examples of this practice, putting the spotlight squarely on Homer’s god-fearing, mustache-sporting neighbor, Ned Flanders.

After his house is destroyed in a hurricane, Ned begins to question his faith in both the world and god. In a standout moment, he lashes out at everyone in Springfield after the new house they try to build for him crumbles to the ground. There aren’t many shows that would be able to achieve such hilarity while shying the focus away from the main characters.

Lemon Of Troy

24. "Lemon Of Troy" (May 14, 1995)

After some kids from Springfield’s rival town, Shelbyville, steal their legendary lemon tree, Bart, Millhouse, Nelson, and Martin vow to get it back. What follows is a journey into enemy territory that pokes fun at pointless town rivalries, and borders on being a critique of nationalism as a whole. But don’t read too much into this episode—it’s more focused on laughs than anything else.

Seeing Millhouse meet his doppelganger, Bart struggle with Roman numerals, and a hilarious take on the famous story of the Trojan Horse all make this episode work on so many levels. It tends to get overlooked because it aired towards the end of The Simpsons' memorable sixth season, but "Lemon Of Troy" is truly one of the show’s gems.

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Homer And Apu

23. "Homer And Apu" (February 10, 1994)

It’s rare that a celebrity guest star can steal the spotlight in an early Simpsons episode, but James Woods’ role in "Homer And Apu" is easily the half-hour's best characteristic.

After Homer gets Apu fired from the Kwik-E-Mart, Woods replaces him while researching a role, for which he'll play a convenience store clerk. What follows is a glimpse into Woods’ mania as he fights with his oven and harasses customers. Years before Family Guy hopped on the James Woods bandwagon, The Simpsons did it better.

The Cartridge Family

22. "The Cartridge Family" (November 2, 1997)

The subject of gun control will always be controversial for some, and here The Simpsons tackles it with a sarcastic edge that makes both sides of the argument look moronic. Instead of bashing the audience over the head with their opinion on the matter, the writers make Homer the poster child for gun control as he goes around shooting anything and everything after his impulse purchase of a firearm. But having the weapon in his house soon begins to put a strain on his marriage.

The whole thing wraps back around to an emotional climax where Homer gives up his gun for the sake of Marge and the kids. Make no mistake about it, there's a serious message to be heard, but none of that overshadows the humor.

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Treehouse Of Horror

21. "Treehouse Of Horror" (October 25, 1990)

In what has become a yearly tradition, the debut "Treehouse Of Horror" episode isn’t on this list for nostalgic purposes; frankly, it’s still one of the series' all-around greatest achievements. Complete with parodies of The Twilight Zone's classic "To Serve Man" episode, Edgar Allan Poe's "The Raven", and Poltergeist, "Treehouse Of Horror" offers the perfect mix of humor and horror, with some genuinely scary moments, especially in the “Bad Dream House” segment.

However, no segment comes close to topping “The Raven." The masterful Poe poem has been done to death in Hollywood, but no other adaptation has been narrated by the baritone voice of James Earl Jones. It’s moody, beautiful, and arguably one of the most creative moments in Simpsons history.

The Itchy, Scratchy, And Poochie Show

20. "The Itchy & Scratchy & Poochie Show" (February 9, 1997)

"The Itchy & Scratchy & Poochie Show" is one of many examples of The Simpsons' writers poking fun at themselves and their loyal legion of fans. After The Itchy & Scratchy Show hits a ratings lull, the executives behind it freak out and hastily introduce a new character named Poochie to boost viewership. And, of course, it wouldn’t be a Simpsons episode if Homer didn’t get hired to provide the character's voice.

After the publicity stunt fails, the fans become enraged and take it out on their once-beloved cartoon. It's a direct satire of the real-life Simpsons fans who began to kick dirt on the show’s grave once it started declining slightly in quality. Even though the show’s writers take direct shots at these jaded fans here, they still ate this episode with a smile on their faces.

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Homer's Phobia

19. "Homer’s Phobia" (February 16, 1997)

After visiting the mall in order to sell some family heirlooms, the Simpsons befriend a gay shop owner named John, who grows an instant attachment to the family. However, once Homer learns of John’s orientation, he begins to panic and worry that John will spread his sexual preference to Bart.

In an attempt to ensure Bart’s heterosexuality, Homer begins to include his son in manly activities, such as smoking, hunting, and a visit to a steel mill—which just so happens to be a gay steel mill.

Naturally, by the end of the episode, Homer comes to peace with John after he saves Homer from a horde of angry reindeer. "Homer's Phobia" is perfect in the way that it gives audiences a heart-felt lesson in tolerance while also providing enough laughs to never make it seem preachy.

The Mysterious Voyage Of Homer

18. "El Viaje de Nuestro Jomer (The Mysterious Voyage Of Homer)" (January 5, 1997)

Completely trippy and groundbreaking, "The Mysterious Voyage Of Homer" features some of the most bizarre animation styles ever seen on a network animated show. After Homer devours an experimental chili pepper that was crafted in a Guatemalan insane asylum, he wanders off into the desert in a spicy stupor.

A series of hallucinations in the desert leads to Homer meeting a talking coyote(voiced by Johnny Cash); then, Homer begins to question whether or not Marge is his true soul mate. Marital strife is a running theme in The Simpsons, but we've never seen it include a talking coyote or prophetic tortoise before.

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Burns Verkaufen der Kraftwerk

17. "Burns Verkaufen der Kraftwerk" (December 15, 1991)

In this episode, Mr. Burns begins to grow weary of the day-to-day operations of the Springfield Nuclear Plant and decides to sell it off to a group of German investors. Which leads to drastic changes in the running of the plant, and before long Homer is fired due to his gross negligence that has gone unnoticed for years.

While this episode packs in plenty of humor, it will be most remembered for Homers’ fantasy of living in “The Land of Chocolate”, which, of course, occurred in the middle of his performance evaluation. All of the plot threads cleverly come to a head at the end, when Mr. Burns buys back his plant because he realizes that he can’t strike fear into the hearts of his fellow man while being just an average Joe.

Duffless

16. "Duffless" (February 18, 1993)

This is one of the many Simpsons episodes featuring a subplot that's just as good as the main one. After he fails a breathalyzer test, Homer sees his driver’s license get suspended by a judge, and he promises Marge that he will give up drinking for one month. The episode's subplot, meanwhile, revolves around Bart and Lisa competing in the school’s science fair where Lisa tries to prove that a hamster is smarter than her brother.

The two storylines come together beautifully as Homer realizes that his marriage is more rewarding than drinking with his friends, and Bart wins the top prize at the science fair after dressing Lisa’s hamster up like an airplane pilot, capturing the hearts of Principle Skinner and Ms. Krabappel.

There's actually a nice message here, delivered when Homer realizes he would rather spend time with Marge than drink. But that’s quickly shattered by the next episode when he’s downing six packs like they’re water again.

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A Fish Called Selma

15. "A Fish Called Selma" (March 24, 1996)

In what should be considered one of The Simpsons' most bizarre episodes, "A Fish Called Selma" features Aunt Selma getting married to washed-up movie star Troy McClure. Although the marriage is just a sham to reignite McClure’s fledgling career, Selma goes along with it for a while just for the fame and fortune. But in the end, the prospect of raising a family in a loveless marriage is too much for her to bear, and she quickly leaves Troy.

The bizarre part of the episode comes from the underlying subplot which reveals that McClure was ostracized from Hollywood because of a scandal involving his peculiar fish fetish. The sordid issue is further pushed when Fat Tony claims that McClure “sleeps with the fishes,” and viewers catch a bumper sticker on McClure’s car that reads “Follow Me To The Springfield Aquarium."

Homer Badman

14. "Homer Badman" (November 27, 1994)

"Homer Badman" is one of those rare television episodes that has actually become more relevant over time. The plot revolves around Homer being falsely accused of sexually harassing the family’s babysitter, even though it was revealed that he was harmlessly peeling a rare gummy candy from the back of her jeans. What followed was a witch hunt where the media camped outside the Simpson’s home and portrayed Homer as an ass-grabbing pervert.

The satirizing of the media and how they routinely ignore the facts in order to get a news story is absolutely brilliant here. The show’s writers perfectly portray cable news channels as nothing more bloodthirsty shock jocks who only want juicy stories, even if they're not true. The gloves really come off in "Homer Badman," and we couldn't be more pleased with the results.

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Who Shot Mr. Burns?

13. "Who Shot Ms. Burns?" (Parts I & II: May 21, 1995 and September 17, 1995)

As the first Simpsons cliffhanger story that spanned two episodes, "Who Shot Mr. Burns?" left fans everywhere wondering for an entire summer who gunned down Springfield’s most powerful senior citizen. Smithers and Homer were the two primary suspects as their motives and alibis made them seem more than guilty by the end of Part I.

Then, after months of waiting, audiences everywhere found out that it was actually Maggie who had inadvertently grabbed the old man’s gun and shot him in the stomach. It was a tough pill to swallow for fans looking for a more logical conclusion, but it was also a brilliant swerve job by the show’s writers. "Who Shot Mr. Burns?" showed other TV shows how to craft a cliffhanger that packs in a great story while also standing on its own as an entertaining individual storyline.

Homer Goes To College

12. "Homer Goes To College" (October 14, 1993)

There are no emotional plotlines or delicate family moments in "Homer Goes To College"; instead, this episode features rapid-fire jokes that sling off the screen so quickly that it takes multiple viewings to catch everything. Written by Conan O’Brien, "Homer Goes To College" can be considered one of The Simpsons' most genuinely funny episodes, as Homer must graduate from college in order to keep his job.

As expected, Homer fails at every turn by almost blowing up the university and getting distracted by a squirrel mid-lecture. This is Homer at his most incompetent, but it never reaches the eye-rolling proportions of later episodes. It's just pure comedic brilliance that never insults your intelligence, yet never forces you to use it, either.

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Homer The Great

11. "Homer The Great" (January 8, 1995)

In "Homer The Great", Mr. Simpson gets inducted into the Stonecutters Society, which is a group comprised of some of the most powerful citizens in Springfield. Together, they use this power to basically sit around their headquarters eating ribs and drinking beer.

However, as so many people have learned throughout the show's history, the mere presence of Homer is enough to enrage the other members and systematically destroy the whole organization from within. Before that happens, though, the episode features some great laughs and the best musical number The Simpsons has ever had.

Lisa The Vegetarian

10. "Lisa The Vegetarian" (October 15, 1995)

We don’t know what’s more impressive: the fact that The Simpsons was able to get such a memorable episode out of Lisa turning into a vegetarian, or that her lifestyle choice has lasted every episode since then. This episode really does have it all: humor, emotion, a deep story, and a great cameo by Paul McCartney. But the real highlight comes from watching Homer and Lisa butt heads over her new lifestyle choice.

Homer, always the carnivore, doesn’t understand how his daughter can give up meat, and Lisa can’t understand why her choice is such a big deal. That conflict is played to perfection as both characters are stubborn in their own way. Yet, it’s also a natural evolution of a relationship between a father and a daughter who couldn’t be more different than each other.

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Treehouse Of Horror V

9. "Treehouse Of Horror V" (October 20, 1994)

It’s difficult to make a holiday special stand alone as one of the best episodes of a show’s history, but "Treehouse Of Horror V" is so funny and fresh that it easily makes the list.

Featuring a brilliant parody of The Shining, one of the best time travel stories ever, and a horrifying tale about a cannibalistic grammar school cafeteria, this episode has it all. There have been over 20 Treehouse Of Horror episodes during the show’s history, but none can touch this. It’s such a complete package that it’s just as satisfying to watch this episode on Halloween as it is to watch it in the middle of February.

Behind The Laughter

8. "Behind The Laughter" (May 21, 2000)

At the end of the show’s eleventh season, the writers created a Behind The Music spoof that took a look at the trials and tribulations of America’s favorite family, titled "Behind The Laughter." Dealing with the family’s money problems, personal feuds, and Homer’s addiction to prescription painkillers, this mockumentary not only delivers the laughs, but it also serves as a qausi-series-finale before many fans feel the show went downhill.

This self-satirical look at the show is just another example at how the Simpsons’ writers are completely comfortable with taking a few jabs at themselves if it makes for good television. "Behind The Laughter" completely shatters the normal formula of a Simpsons episode, but for longtime fans of the show, there's still plenty to enjoy here.

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Summer Of 4 Ft. 2

7. "Summer Of 4 Ft. 2" (May 19, 1996)

When the Simpson family, along with Millhouse, go to spend a vacation at Ned Flanders’ beach house, Lisa sees this as the perfect opportunity to start fresh and make new friends that don’t know her reputation as a bookworm. Thus, "Summer Of 4 Ft. 2" is for anyone that has ever felt out-of-place whether at parties, school, or work. It’s well-written and sentimental, without seeming overly sappy or hokey.

And while Lisa uses her vacation to do some soul-searching, Homer spends his time at the beach buying illegal fireworks, disposable enemas, and enough porn to fill the racks at a sperm bank. It all comes together nicely at the end when Lisa is finally accepted by her new friends, but it's somewhat bittersweet to know she'll go back to being ostracized in Springfield.

22 Short Films About Springfield

6. "22 Short Films About Springfield" (April 14, 1996)

Every season, Simpsons fans are usually treated to an episode that breaks the mold of the normal story format and gives us something unique. "22 Short Films About Springfield" accomplishes this by crafting an episode of interconnected plots revolving around the day-to-day lives of various citizens of Springfield.

Throughout the episode, viewers are treated to a hilarious parody of Pulp Fiction, a glimpse at Apu’s sex life, and the shocking realization that Reverend Lovejoy’s dog uses Ned Flanders’ lawn as his own personal bathroom. This is an incredible mishmash of plots that converge by the end in a way that most Hollywood filmmakers can only dream of.

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Homer The Heretic

5. "Homer The Heretic" (October 8, 1992)

It’s no secret that the Simpson family hasn’t exactly seen eye-to-eye with God over the years, but "Homer The Heretic" takes the issue of religion on in full force. After Homer decides to skip church on a Sunday in order to stay in bed and make a “Space-age, out-of-this-world Moon Waffle” (which is just a waffle wrapped around a stick of butter), he comes to the realization that he doesn’t need religion in his life at all.

Despite numerous attempts to get him back on the Christian bandwagon, Homer continues to stay inside to fulfill all of his hedonist desires. That is, until his house catches fire because of one of his lit cigars, and he's saved by Flanders. "Homer The Heretic" is one of the show's more philosophical episodes, and even features a cameo by God himself, who, interestingly enough, is the only character in the history of The Simpsons to have five fingers.

Last Exit To Springfield

4. "Last Exit To Springfield" (March 11, 1993)

"Last Exit To Springfield" revolves around Homer becoming the head of the Springfield Nuclear Plant Union. This all happens after the employees lose their dental plan, and with Lisa in need of braces, Homer galvanizes the workers to fight for what is theirs. Aside from being filled with great humor, such as “The Big Book of British Smiles” and Lisa’s transformation into a social outcast after being fitted with headgear, this episode is also socially relevant in a way that cartoons rarely ever achieve.

Instead of slogging through newspapers and history books to get a good idea of the conflict between the labor unions and business owners that goes on in America, just watch "Last Exit To Springfield." Trust us, it's a lot more entertaining this way.

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Homer's Enemy

3. "Homer’s Enemy" (May 4, 1997)

Easily the most controversial episode on the list, "Homer’s Enemy" has inspired differing opinions amongst both the fans and the show’s creators. The plot deals with a hard-working man named Frank Grimes who begins to work with Homer at the nuclear plant. As Grimes—or “Grimey,” as Homer calls him—begins to see how Homer’s gross negligence has been rewarded throughout the years in the form of a nice house and beautiful wife, he quickly goes mad and winds up being killed while in a rage.

It’s the most mean-spirited episode of the series, but there's also a brilliance here that can't be denied. Homer plays the slothful villain of the piece, yet Grimes is the one that suffers. There is nothing likeable about Homer here, yet watching him unintentionally drive Grimey to self-destruct is just so satisfying. It might be a bit dark for some, but "Homer’s Enemy" is one of The Simpsons' most complex and interesting episodes.

Lisa's Substitute

2. "Lisa’s Substitute" (April 25, 1991)

Deftly blending the show’s trademark humor with some deep-rooted emotional beats, "Lisa's Substitute" shows Homer attempt to connect with his daughter, despite the fact that they have nothing in common. Instead of looking up to her oafish father, Lisa gains an attachment to her substitute teacher, Mr. Bergstrom (voiced to perfection by Dustin Hoffman). He's smart, thoughtful, and understanding—three traits that Homer sorely lacks. But by the end, he teaches them both more about each other than they ever could have realized.

Unlike those in later seasons, this episode is firmly entrenched in reality as it plays out more like an art-house drama than an animated sitcom. However, there are also plenty of laughs that come at the expense of Homer and Lisa’s strained relationship. "Lisa’s Substitute" further proves that you don’t need zany non-sequiturs or crude jokes to capture an audience.

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Cape Feare

1. "Cape Feare" (October 7, 1993)

Whether it’s parodying classic films or crafting gut-busting original humor, "Cape Feare" is a prime example of what a Simpsons episode should be. It has a great story, amazing voice-acting (especially by Kelsey Grammer, as Sideshow Bob), and some of the most memorable jokes in the show’s history. Gags like Sideshow Bob’s rake fiasco or the Witness Protection Program attempting to get Homer to follow a simple command are just the tip of the iceberg here.

The episode is, as the title implies, a spoof of the film Cape Fear, as Sideshow Bob hunts the Simpsons down for landing him in prison, but it reaches comedic heights that no other animated show has ever come close to replicating. Make no mistake about it, this episode doesn’t feature any emotional or dramatic moments, but every inch of "Cape Feare" should appeal to anyone with a pulse.

The show's fifth season was arguably its peak, and "Cape Feare" manages to raise the bar even higher. It may take more than one viewing to catch all of the jokes, but after you’ve seen it once, you’ll want to watch it again and again.

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