Best Simpsons Episodes: Top 5 Must-Watch Classics Most Recommended By Fans

“The Simpsons” has been entertaining people across the globe since 1989. Beginning its astounding 35th season, we’ve lost count of how many memorable moments there have been in more than 750 episodes and a major motion picture. Homer, Marge, Bart, Lisa, and Maggie will forever be ingrained in our culture. How does one try to find the best episodes from this series? Well, everything’s coming up Milhouse here at StudyFinds, and we were able to find the top five best “Simpsons” episodes for fans to watch next.

“The Simpsons” currently holds three television records that might never be broken. After debuting in 1989, “The Simpsons” is the longest-running American animated series, the longest-running American scripted primetime series, and the longest-running American sitcom. And it shows no signs of slowing down anytime soon. The series has been renewed through 2025 and is expected to pass the 800-episode mark.

For 35 seasons, Bart Simpson has been a major headache for his fourth-grade teacher Edna Krabappel (before her voice actor Marcia Wallace passed away) and Principal Seymour Skinner. Even though Bart doesn’t come across as the brightest bulb, the class clown does have his moments where he might be the smartest guy in the room. And that shouldn’t come as a surprise, as a study shows that class clowns might also be the most intelligent students. Turkish researchers say strong humor skills during adolescence may be a sign of high intelligence. Scientists state children with higher than average levels of general knowledge and verbal reasoning tend to excel at humor. So never count Bart out!

Are you ready for a “Simpsons” binge? StudyFinds has compiled the top five best “Simpsons” episodes of all time. Is one of your favorites not included? Let us know in the comments below!

Simpson figurines
Simpson figurines (Photo by Stefan Grage on Unsplash)

The List: Best “Simpsons” Episodes, According to Experts

1. “Marge vs. the Monorail,” Season 4, Episode 12

Topping the list is the iconic “Marge vs. the Monorail.” Comic Phil Hartman voices Lyle Lanley, where he performs what might be the greatest “Simpsons” song of all time in “Monorail.” “Charismatic scammer Lyle Lanley comes to town, selling the residents on the appeal of the monorail — despite it not actually being needed,” writes Variety. “Nearly all of the residents, outside of Marge and Lisa, get swept up in monorail-mania. Phil Hartman delivered an incredible performance as Lyle, who needed the right amount of arrogance and gravitas to pull off the scam. And the ‘Monorail’ song remains one of the show’s very best.”

“Mr. Burns is forced to pay a $3 million polluter’s fine, and Springfield gets to decide how they’ll spend this sudden influx of cash. Marge has the town enthused to finally fix up Main Street when in walks Lyle Lanley (voiced by Phil Hartman). After a very catchy song and dance number, the town impulsively buys a monorail from him. Lanley’s hasty training and random appointment of Homer as conductor leaves Marge to save Springfield from its dangerous new investment,” notes Collider. “Written by Conan O’Brien, this episode was instantly embraced by both fans and critics. It continues to be beloved due to its Flintstones-inspired opening, a spectacular Simpsons musical number, a surprising cameo by Leonard Nimoy, iconic details such as the popsicle stick skyscraper and the escalator to nowhere, and memorable lines like ‘I call the big one Bitey.'”

Kotaku says some people took issue with this specific episode when it came out in 1993. “It’s funny to remember that, back when this episode aired in 1993, it caused some controversy among fans and viewers over its less grounded, more over-the-top plotline and jokes. And yeah, ‘Marge vs. the Monorail’ is very weird compared to what had come in the previous four seasons. I mean, Star Trek’s Leonard Nimoy literally teleports away. But who cares! This Conan O’Brien-penned episode features the Monorail song and a lot of Phil Hartman as the singing con artist, Lyle Lanely. How can you hate that?”

2. “Cape Feare,” Season 5, Episode 2

“‘Cape Feare’ spoofed the classic revenge film Cape Fear and its 1991 remake, as well as slasher films in general. With Bob on the loose and sending Bart death threats, the Simpsons had no choice but to enter witness protection and become ‘The Thompsons.’ But even that wasn’t enough to halt Bob’s warpath. Garden rakes, on the other hand…,” writes IGN. “Here is another episode where the quality of the writing elevated everything. From Bart seeing potential killers around every corner to Bob being tricked into performing the entirety of The H.M.S. Pinafore, the laughs never let up. And it showcased Bob at his most deliciously evil. Later Bob episodes have given him a family and complicated his relationship with the Simpson family. There’s something to be said for his single-minded obsession in this episode.”

“The Simpsons is, at its heart, one big parody, but even Homer Thompson could recognize ‘Cape Feare’ as the show’s most meticulous and manic pop-culture takeoff,” notes Entertainment Weekly. “Not only is it a pitch-perfect send-up of the Martin Scorsese remake (with Kelsey Grammer’s Sideshow Bob traveling to Terror Lake to hunt down and murder his pint-size nemesis, Bart), but it also features one of the most bizarre scenes in television history. We’re referring, of course, to the rakes. Think about it. How many other series would waste valuable prime-time real estate by showing a man whacking himself in the face with a garden rake not once, not twice, but NINE TIMES?!? If ever there was a gag genius in its repetitive stupidity (progressing from funny to not so funny to the funniest thing ever), this is it—merely the sharpest cut in an entire episode that just plain kills.”

Game Rant says IMDB gave the episode an exceptional 9.2 rating. Why? “Sideshow Bob gets out of prison and terrorizes the Simpson family into witness protection in ‘Cape Feare,’ a spot-on parody of Martin Scorsese’s remake of Cape Fear. From Bob’s hilariously drawn-out rake gag to Homer’s inability to grasp his new identity as Homer Thompson, ‘Cape Feare’ is filled with classic Simpsons moments that’ll never get old. The ending is also excellent and an example of The Simpsons at the absolute peak of its powers.”

3. “22 Short Films About Springfield,” Season 7, Episode 21

Coming in third on the list is “22 Short Films About Springfield” which features some of the background characters of the show. “Many great episodes of this show gave us memes, but ’22 Short Films About Springfield’ gave us ‘steamed hams,’ which has become one of the internet’s best memes,” says ONE37pm. “This episode is a series of vignettes and short stories that take place all over Springfield. While this is the sort of entry that could potentially buckle under the weight of all those storylines, ’22 Short Films About Springfield’ is able to interconnect them, even if those plot threads can be a little loose.”

“The Simpsons are at the core of the show that bears their name, but this season 7 episode allowed viewers to focus on the many other colorful characters that inhabit Springfield,” writes Digital Trends. “Framed as a series of vignettes, 22 Short Films About Springfield packs so many stories into its tight running time that it can feel overwhelming, but the jokes are so good that you won’t mind watching it over and over again.”

Rolling Stone notes “22 Short Films About Springfield” adopted “Francois Girard’s obscure, art-house film Thirty Two Short Films About Glenn Gould as the basis for an entire episode.” “Cinema nerds could nod approvingly; everyone else could enjoy the show’s broadest representation of Springfield’s vast universe to date. Only in the Simpsons can random, barely-there characters like Chesparito (A.K.A. Bumblebee Man) and Cletus Spuckler (A.K.A. Cletus the Slack-Jawed Yokel) get their own slice-of-life mini-episodes. ‘Sometimes I wonder about all the people in this town,’ says Bart in the beginning of the episode. He’s not the only one.”

4. “Homer at the Bat,” Season 3, Episode 17

“Homer at the Bat” was every baseball fan‘s dream, featuring cameos from Ken Griffey Jr., Ozzie Smith, Don Mattingly and others. “After placing a large bet on the outcome of a game, Burns decides to bring in ringers to the plant’s baseball team — MLB players Roger Clemens, Wade Boggs, Ken Griffey, Jr., Steve Sax, Ozzie Smith, José Canseco, Don Mattingly, Darryl Strawberry and Mike Scioscia,” writes Variety. “One by one they fall off the roster, until Homer is the only regular player left on the bench. Despite that, he manages to still save the day: He gets brought in as a pinch-hitter and gets hit by the pitch, bringing in the winning run. The episode is perfectly ridiculous, while still allowing Homer to get the victory — even if it was at the expense of his dignity. It was one of the most effective uses of guest voices in the show’s three-decade run and its legacy includes the hour-long mockumentary ‘Springfield of Dreams: The Legend of Homer Simpson,’ which aired in honor of the episode’s 25th anniversary.”

“Thanks to the nine players who contributed, it’s an iconic episode that showcases the power of the Simpsons‘s allure to draw in unusual cameos,” notes Time Magazine.

ONE37pm calls “Homer at the Bat” the very best “Simpsons” episode. “In an effort to bolster the rankings of the nuclear power plant’s softball team, Mr. Burns hires major league baseball players such as Roger Clemens, Wade Boggs, Ken Griffey Jr., Steve Sax, Ozzie Smith, José Canseco, Don Mattingly, Darryl Strawberry, and Mike Scioscia, who all guest starred as themselves. It provides some of the most absurdist humor in the series, such as Boggs getting knocked out by Barney in an argument over British prime ministers and Smith getting lost in another dimension. Nothing makes sense, but everything comes together tightly in a perfect half hour of television.”

5. “Mr. Plow,” Season 4, Episode 9

Rounding out the top five is the classic “Mr. Plow.” “Although Homer spends most of The Simpsons working at the power plant, he’s accumulated some memorable side gigs over the course of his many years on the show. One of the most memorable, though, was Mr. Plow, when he became a minor celebrity because of his snow-plowing business,” writes Digital Trends. “When Homer’s drinking buddy Barney decides to get into the business as the Plow King, the rivalry between the two comes pretty close to a boil. Along the way, we get plenty of perfect joke delivery and loads of memorable moments between Barney and Homer.”

“One of those episodes that can be summed up as ‘Homer makes it big and then loses it all,’ ‘Mr. Plow’ might be the best example of this formula. Homer starts a snow plowing company that eventually hits it big. While things initially are great, Homer loses his customers to a rival business run by Barney,” explains Game Rant. “Hilarious cameos, intelligent gags at commercials, and a memorable climax that is genuinely riveting, ‘Mr. Plow’ is a stunning comedic work of art from beginning to end.”

Every “Simpsons” fan will never forget Mr. Plow’s jingle. “Okay, everyone, sing it with me: ‘Call Mr. Plow, that’s my name, that name again is Mr. Plow.’ Sure, the song and snow plow rivalry between Homer and Barney is the real meat of this episode. But I think it often means people forget about the incredible Adam West cameo in this classic,” says Kotaku. “It should be noted that this was before his stint on Family Guy and his resurgence as an odd but loveable goof who used to play Batman. ‘And how come Batman doesn’t dance anymore?'”

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Note: This article was not paid for nor sponsored. StudyFinds is not connected to nor partnered with any of the brands mentioned and receives no compensation for its recommendations.

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About the Author

Matt Higgins

Matt Higgins worked in national and local news for 15 years. He started out as an overnight production assistant at Fox News Radio in 2007 and ended in 2021 as the Digital Managing Editor at CBS Philadelphia. Following his news career, he spent one year in the automotive industry as a Digital Platforms Content Specialist contractor with Subaru of America and is currently a freelance writer and editor for StudyFinds. Matt believes in facts, science and Philadelphia sports teams crushing his soul.

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