The 15 Funniest Moments In The Simpsons, Ranked

It's almost impossible to believe that "The Simpsons" is still on the air. The groundbreaking animated sitcom has been delighting audiences since 1989. "The Simpsons" was unlike anything else when it first premiered. While there had been occasional animated films like "Fritz the Cat" that were aimed at older viewers, "The Simpsons" told stories similar to the family comedies that dominated the era.

"The Simpsons" has grown and evolved since its debut. It's easy to see how the show has influenced the history of adult animation. We wouldn't have programs like "South Park," "Family Guy," "King of the Hill," or "American Dad!" without the precedent that "The Simpsons" established.

Like all shows that have been running for a long time, "The Simpsons" has suffered a decline in quality. The first ten seasons rarely featured a bad episode, but sadly, "The Simpsons" is no longer a must-watch show. That being said, the Springfield gang can occasionally pull off something surprising. Now that the rights to "The Simpsons" belong to the Walt Disney Company, Disney+ has released crossover shorts with the Marvel Cinematic Universe and the "Star Wars" franchise.

Here are the 15 funniest moments in "The Simpsons," ranked.

15. Hank Scorpio's Evil Plans, You Only Move Twice

Given how long "The Simpsons" has been airing, there have been many episodes that lampoon cinematic classics. One of the few franchises that is older than "The Simpsons" is the James Bond series. Since 1962's "Dr. No," 007 has been going on globetrotting adventures and using different gadgets. Every generation has their favorite Bond movie, but there are aspects of the franchise that haven't changed at all.

"The Simpsons" provided the perfect 007 parody in the classic episode "You Only Move Twice." Although the title is a reference to the 1967 film "You Only Live Twice," the episode makes fun of the various cliches that recur in the series. Albert Brooks guest stars as Hank Scorpio, a ridiculous supervillain who places Homer in charge of a nuclear system.

What's hilarious about the episode is how clueless everyone seems about how evil Scorpio is. He's intent on completing his dastardly plan, but no one seems to notice.

14. Grimes Goes Crazy, Homer's Enemy

Although the best moments of "The Simpsons" are when Homer shows his true colors and does something kind for his family, his incompetence and laziness give him more than a few enemies to deal with. Homer's job at the Springfield Nuclear Power Plant gives him and his friends Lenny and Carl the chance to sit around and do almost nothing.

Homer's workplace activities draw the ire of one of his fellow employees in the Season 8 episode "Homer's Enemy." In a story that loosely parodies Joel Schumacher's "Falling Down," Homer is assigned to work alongside Frank Grimes, a hardworking new hire. Grimes is shocked that Homer doesn't take his job seriously. While Grimes tries to earn the respect of Mr. Burns, he's blamed for a workplace accident that Homer is responsible for.

Grimes' extended rant about Homer's refusal to change is hilarious, especially since Homer is clueless as to why his new coworker is so angry. Grimes' accidental death remains one of the darkest jokes in the history of "The Simpsons."

13. David Duchovny and Gillian Andersons' Cameos, The Springfield Files

"The Simpsons" frequently features celebrity guest stars. While sometimes these guests appear as themselves, the Season 8 episode "The Springfield Files" featured both David Duchovny and Gillian Anderson as Fox Mulder and Dana Scully, their characters from "The X-Files." "The Springfield Files" is constructed like an episode of "The X-Files." When Homer reports an alien sighting, Mulder and Scully venture to Springfield to investigate the mysterious occurrence.

The best parody episodes of "The Simpsons" are the ones that are funny regardless of how familiar you are with the property that's being targeted. There are a lot of fun references to "The X-Files," but even if you've never seen the series, Homer's comic attempts to make contact with the aliens are still hilarious. Duchovny and Anderson do a great job at treating "The Springfield Files" with the same gravity as an episode of "The X-Files." Their seriousness makes Homer's incompetence stand out even more.

12. The Poochie Fad Fades, The Itchy & Scratchy & Poochie Show

"The Simpsons" writers satirize trends in television and pop culture through the in-universe cartoon series "Itchy & Scratchy." The absurdly violent parody of "Tom and Jerry" goes to very dark places, but children like Lisa and Bart simply think that it is hilarious. This shows how ignorant parents are of what their children are watching.

In Season 8, "The Simpsons" targeted trends in TV to "modernize" shows to appeal to a more youthful audience. "The Simpsons" had managed to avoid adding new characters for the sake of branching out to different viewers, but other sitcoms weren't so lucky. In "The Itchy & Scratchy & Poochie Show," Homer lands the role of the "hip" new character Poochie on "Itchy & Scratchy." Poochie fails to impress the loyal "Itchy & Scratchy" audience. He elicits such anger from the fans that the humbled network decides to remove the character.

This is a hilarious way to examine the relationship that television fans have with their favorite shows. It's particularly amusing to watch Homer get ostracized from the community for being involved with the Poochie character.

11. The Shinning, Treehouse of Horror V

The "Treehouse of Horror" episodes are a staple of "The Simpsons." These anthology Halloween episodes have allowed "The Simpsons" to create comical versions of popular horror films and break from the traditional structure of the show's narrative. 

The segment titled "The Shinning" parodies Stanley Kubrick's "The Shining." The Simpson clan is tasked with taking care of Mr. Burns' lavish estate, which looks a lot like the Overlook Hotel. However, Mr. Burns makes the mistake of shutting off his television connection and purging the mansion of beer. With no TV to watch and no beer to drink, Homer goes into a Jack Torrance-esque rage.

"The Shining" parody concludes perfectly with Homer chasing his family around the house with an ax. It's always fun when "The Simpsons" gets a little dark with its humor, and "The Shinning" features more blood and gore than an average episode.

10. Homer's First Flight, Deep Space Homer

Homer gets the chance to go to space in the Season 5 episode "Deep Space Homer." After he prank calls NASA, the space agency decides that sending an "average joe" on a voyage to the stars may help them improve their Nielsen ratings. Homer and Barney are selected for the mission. They go through astronaut training with Apollo 11 astronaut Buzz Aldrin, who appears as himself in a guest role.

Barney initially impresses everyone when he sobers up and takes the job seriously, but he soon falls back into his old ways. Homer is chosen to lead the mission. He somehow manages to smuggle a bag of potato chips into the spacecraft and accidentally spills an ant farm during his first flight.

Later seasons of "The Simpsons" would "jump the shark," and feature completely madcap storylines that were too far-fetched. "Deep Space Homer" risks falling into this category, but the comical element of NASA trying to improve their ratings adds an element of satire.

9. Homer's Ode to Marge, The Simpsons Movie

By the early 21st century, "The Simpsons" had suffered a massive decline in quality. The most beloved characters had transformed into more basic versions of who they once were. Homer did nothing but act like a selfish jerk, Marge was clueless to the point of absurdity, Bart was irredeemably lazy, and Lisa used her intelligence to make other people feel bad about themselves. Against all odds, "The Simpsons Movie" managed to return the heart to the beloved characters when it debuted in theaters in 2007.

"The Simpsons Movie" is great because it understands that Homer is a good guy — despite his obvious flaws. Homer's stupidity forces the family to flee Springfield and seek refuge in Alaska. With all the odds stacked against him, Homer shows compassion for his long-suffering wife. He gives a heartfelt list of her attributes when they share an intimate moment in their cabin. It's genuinely sweet in a way that "The Simpsons" hadn't been in quite some time.

8. Young Homer and Marge, The Way We We Was

Although "The Simpsons Movie" reinstated the importance of Homer and Marge's romance, "The Simpsons" gave the couple their origin tale back in Season 2. The episode "The Way We Was" was the series' first flashback installment. Set in 1974, this episode explores Homer and Marge's first date. Homer tells this story to Bart, Lisa, and Maggie when their television signal cuts out.

Seeing the teenage versions of Homer and Marge is hilarious. It's strange to see Homer with hair! In many ways, they hadn't changed at all. Homer is a slacker and enjoys cutting class to hang out with Barney. Marge is an outspoken advocate for social issues, but she's limited in what she can do by her family.

Although Marge initially goes to their high school prom with Homer's rival, Artie, she eventually recognizes the virtue of her future husband. Marge and Homer share a genuinely heartfelt dance and swear to remain loyal to each other. This grounded their relationship and even cast Homer in a sympathetic light. You also get to hear the kids' commentary on their parents' love affair. Lisa loves the story, but Bart thinks that it's gross.

7. Sideshow Bob Goes Back to Jail, Cape Feare

There is no villain in "The Simpsons" universe who is more fearsome than Sideshow Bob. The former assistant to Krusty the Clown was so infuriated by his employer's ignorance that he turned into a vicious criminal. Although Sideshow Bob has sworn vengeance on Krusty, his plot is revealed by Bart in the episode "Krusty Got Busted." Sideshow Bob is sent to prison. He begins dreaming of the day that he will be able to get his revenge and murder Bart.

Bart has learned to fear Sideshow Bob. In the Season 5 episode "Cape Feare," Sideshow Bob escapes from prison. Although he is almost able to corner Bart on a boat, the young Simpson distracts the evil genius by surprising him with a compliment on his extraordinary voice. Sideshow Bob launches into a hilarious impromptu musical number.

This gives Bart enough time to escape, and once again, Sideshow Bob is arrested by Chief Wiggum. This sets up the possibility of Sideshow Bob's return while promising "The Simpsons" fans that he will never succeed. The references to both versions of "Cape Fear" are the icing on the cake.

6. Homer Designs the Perfect Drink, Flaming Moe's

Grumpy bartender Moe Szyslak is one of the most hilariously tragic characters in "The Simpsons." Although Moe thinks that he has many friends because of how many people visit his tavern, Homer and his companions only go for the beer. Moe's Tavern is hit with a financial crisis in the episode "Flaming Moe's." Moe gets a chance to improve his luck when Homer gives him the recipe for the perfect drink.

Homer once poured Krusty brand cough syrup into an alcoholic drink, and accidentally set it on fire. Surprisingly, this warm drink is delicious. Moe finds that his customers enjoy Homer's odd mix of ingredients. His fortunes change overnight. Suddenly, Moe's Tavern is the place to be. However, "The Simpsons" fans know that Moe's luck is never going to last very long.

Sadly, Moe's plan to sell his secrets to a popular restaurant chain is ruined when Homer blurts out the recipe in front of the potential buyers. When they learn that the mix is nothing but alcohol, cough syrup, and a little fire, they take back their offer. Moe is hilariously trapped in the same position he was in before.

5. Mark Hamill's Cameo, Mayored to the Mob

In recent years, "The Simpsons" has become overly reliant on famous guest stars. Although it is always fun to see celebrities pop up as themselves and deliver some self-referential humor, simply including a cameo is not a joke in itself.

However, "The Simpsons" delivered one of its best cameos way back in Season 10 when Mark Hamill appeared in the episode "Mayored to the Mob." It's not the only time that "The Simpsons" includes "Star Wars" references, but the episode delivers a surprisingly accurate depiction of obsessive fan culture. Hamill does more than just make fun of himself. He shows the pressures of having to be "Luke Skywalker" all the time.

Homer rescues Hamill and Mayor Quimby from a fan convention that descends into chaos. Impressed with his skills, Quimby decides to employ Homer as his new bodyguard. At the end of the episode, Homer decides to abandon his new boss and save Hamill from the paparazzi instead. 

4. The Truth is Revealed, Who Shot Mr. Burns? (Part 2)

"The Simpsons" lampooned the drama series "Dallas'" infamous "Who Shot JR?" cliffhanger with the two-part episode "Who Shot Mr. Burns?" The first half aired at the very end of Season 6, but the mystery wasn't solved until the beginning of Season 7. This gave "The Simpsons" fans time in between to come up with theories. Which Springfield resident was responsible for the near-fatal shooting of the business tycoon Mr. Burns?

The solution to the mystery is just as ridiculous as you would expect. Mr. Burns had gotten into a fight with baby Maggie over her favorite lollipop. Desperate to take back her candy, Maggie inadvertently shot Mr. Burns. Not only is this a great payoff, but it creates additional humor by drawing comparisons between the two characters. Both Maggie and Mr. Burns behave like children — but Maggie has an excuse!

Even if you've never seen "Dallas," the "Who Shot Mr. Burns?" mystery can be compared to any number of television shows that try to create fanfare with a cliffhanger episode. Although the mystery is solved and Maggie avoids jail time, some dedicated "The Simpsons" fans have speculated that there was a different culprit.

3. Homer Accepts Santa's Littlest Helper, Simpsons Roasting on an Open Fire

This is the one that started it all! "The Simpsons" didn't truly define itself until Season 2, but there are a few gems from the first season that are worth remembering. The very first episode, "Simpsons Roasting On An Open Fire," establishes some important precedents for the show. Even though they frequently descend into bickering, the Simpsons do care for each other. Homer manages to give his family the perfect holiday present.

Homer is desperate to buy gifts for Marge, Bart, Lisa, and Maggie. He fails to receive a holiday bonus at work and takes a job as a mall Santa Claus to make ends meet. Homer frequently embarrasses himself on "The Simpsons," but in this episode, it's for a good cause. Unfortunately, the gig doesn't give Homer enough money to spend on expensive presents.

Homer bets his money on a small racing dog named "Santa's Little Helper." When Santa's Little Helper loses, Homer decides to adopt the dog. Homer's realization that Santa's Little Helper is just as pathetic as the rest of the family is both funny and heartfelt. It epitomizes the best that the show can be.

2. The Mr. Plow Jingle, Mr. Plow

In the Season 4 episode "Mr. Plow," Homer is talked into buying a snowplow by a manipulative salesman. Homer's gullible nature is always humorous. However, he shows that he can make the best of the situation.

Ironically, Homer must clear people's driveways using his new snowplow so that he can pay for it. Although his initial efforts to court customers aren't very successful, Homer gets a valuable suggestion from Lisa. She tells him that he might be able to attract a larger crowd if he runs a commercial on late-night television. Homer comes up with his signature "Mr. Plow" jingle. "Call Mr. Plow, that's my name. That name again is Mr. Plow!"

Homer is at his most endearing when he is enthusiastic. Even though he isn't very bright, Homer's excitement about the "Mr. Plow" idea is more entertaining than the times when he acts like a selfish jerk. Of course, the success of "Mr. Plow" is only temporary, but that doesn't mean that Homer goes home empty-handed. Marge asks him to put on the "Mr. Plow" jacket before they share an intimate evening.

1. The Monorail Song, Marge vs. The Monorail

"The Simpsons" has never had a more hilarious moment than the classic "The Monorail Song" in Season 4. With its inventive wordplay and homages to "The Music Man," this moment is everything that "The Simpsons" does best.

Season 4 was a creative high for "The Simpsons" and featured some of the show's best writers. A young Conan O'Brien wrote the script for "Marge vs. The Monorail," which remains one of the best installments of the season. Scheming salesman Lyle Lanley (Phil Hartman) comes to Springfield to propose the creation of a monorail system. Marge has doubts about the safety of Lanley's suggestion. However, the rest of the town is utterly charmed by Lanley's hilarious musical proposal.

Hartman had a great voice, but "The Monorail Song" allows the other characters to participate in the musical sequence. It's a great snapshot of how easily Springfield gets caught up in current fads. The episode is remembered to this day. Conan O'Brien even performed the classic tune in front of a live audience at "The Simpsons Take the Hollywood Bowl" concert.