With The Simpsons being the most popular cartoon show of all time in the West and the longest-running animated TV series, it's hard to choose any set of "best episodes," let alone just 15 of them.
Creator Matt Groening has been in charge of the family-centric animated sitcom since 1989, which currently spans over 700 episodes across 32 seasons (and is still ongoing as of this writing).
While most fans would agree that The Simpsons peaked somewhere between seasons 9 and 12, its continued persistence serves as proof that too much of a good thing can be bad.
But when The Simpsons was good, it was REALLY good, providing countless hours of witty humor and pop culture references. Here are my picks for the best Simpsons episodes of all time!
15. "I Love Lisa" (Season 4, Episode 15)
Since the release of this episode in 1993, all kinds of people have been buying their partners funny Simpsons-themed cards on Valentine's Day, especially now that online shopping is so easy!
"I choo-choo-choose you" is the card Lisa gives to Ralph Wiggum on the big day. The thing is, Lisa only gives it to him out of pity because everyone else gets a card and he's the only one who doesn't.
Despite his worryingly low IQ and tendency to pick his nose, I probably would've given him one too after seeing him cry in the corner.
This kind act lands Lisa in a tight spot as Ralph falls in love with her and she can't bear to let him down. However, those repressed feelings are bound to boil over and explode... which they do on live TV.
14. "Homer at the Bat" (Season 3, Episode 17)
Homer has held so many different jobs over the course of The Simpsons: Mr. Plow, chef, grease salesman, imitation Krusty, astronaut, fortune cookie writer, food critic, carny, missionary, Kwik-E-Mart cashier, hippie, garbage commissioner... The list is practically endless.
Although most of his career changes are fun to watch—which are temporary before he inevitably settles back to being a nuclear safety inspector—my favorite is from season three, back before Homer lost his heart and became a selfish, braindead stereotype.
In this episode, after making his own lucky baseball bat, Homer ensures that the power plant's softball team always win. Not only is it a great classic episode, but it also saved two real lives when viewers recalled seeing a poster for the Heimlich maneuver on the wall!
13. "Marge vs. The Monorail" (Season 4, Episode 12)
The Simpsons is partial to a little sing-song, like in "Homer's Barbershop Quartet," "Two Dozen and One Greyhounds," "Homer and Apu," "Radio Bart," "Stark Raving Dad," and "Bart After Dark."
But the catchiest one has to go to "The Monorail Song," in which con artist Lyle Lanley sings his way into selling a dodgy monorail to Springfield. (To be fair, they should have known it was fake after Lanley appointed Homer as its conductor...)
TV host Conan O'Brien wrote this episode and openly stated that this one is his favorite of all the ones he came up with. Interestingly, Yeardley Smith (who voices Lisa Simpson) thought it was one of the show's worst! But fans tend to side with O'Brien on this one.
12. "The Springfield Files" (Season 8, Episode 10)
One search on Etsy or Depop will bring up hundreds of stickers, badges, pins, t-shirts, hats, statues, magnets and cross-stitches of Mr. Burns as a googly-eyed alien. All thanks to this episode!
His huge pupils, glowing green aura, and benevolent lexis made alien Burns an immediate meme, his voice soft and sweet as he claims: "I bring you love." Yeah, it doesn't sound anything like Mr. Burns, who's more like a parody of the tight-fisted Ebenezer Scrooge.
Turns out, Mr. Burns is only talking and floating like that because of his longevity treatment, as he's implied to be well into his 100s.
The references to the characters and theme tune of The X-Files are what make "The Springfield Files" a slam-dunk episode, further boosted by Leonard Nimoy's guest appearance!
11. "Cape Feare" (Season 5, Episode 2)
In the show's early days, The Simpsons leaned heavily on recurring gags to give us familiar laughs, but without putting its whole weight on them. For example, the prank calls to Moe or Homer strangling Bart (which has since been retired as "inappropriate").
Another great gag? Sideshow Bob stepping on rakes!
This one most notably occurs in "Cape Feare," a parody of the thriller film Cape Fear. The episode received an Emmy nomination purely for the scene where Bart's evil British enemy gets hits in the face repeatedly with rakes—and shudders every time.
Intentionally dragging out a joke is a favorite of The Simpsons (like Homer dialing for an age in "In Marge We Trust"), and this perfect example is cited among the most memorable scenes in the show.
10. "Bart Sells His Soul" (Season 7, Episode 4)
This one's not only one of my favorites, but also a favorite of Nancy Cartwright (voice actor for Bart Simpson)!
As punishment for a prank, Bart is made to clean the church organ pipes with Milhouse. There, he proclaims to Milhouse that there's "no such thing as a soul" and sells his own for five dollars.
However, the piece of paper reading "Bart Simpson's Soul" proves a lot more valuable than Bart initially realized. Strange phenomena start to unravel before him: automatic doors won't open, his breath won't fog up glass, and he no longer finds his favorite TV show funny.
Lisa warns Bart about the dangers of losing his soul, giving viewers some philosophical theories to mull over. Panic-stricken, he tries to buy back the paper, only to find that Milhouse has already sold it.
9. "And Maggie Makes Three" (Season 6, Episode 13)
The Simpsons is a comedy, but the best episodes are the ones that tug on the old heartstrings. You wouldn't be judged for shedding a tear at the end of "And Maggie Makes Three." Who knew yellow cartoon drawings could have such an emotional impact?
One of the show's many flashback episodes, "And Maggie Makes Three" tells the story of why there are no baby pictures of Maggie in the photo album. As it turns out, Maggie's arrival was less than good news, forcing Homer to quit his dream job at the bowling alley.
After begging for his old job back, Mr. Burns nails a plaque to his office wall, reading: "Don't Forget, You're Here Forever." Of course, once Maggie arrives, Homer is over the moon. He sticks the photos where he "needs them most" to remind himself to "Do It For Her." (Wipes tear.)
8. "Homer's Enemy" (Season 8, Episode 23)
One of Homer's main character traits is his sheer dumb luck. He almost meets his demise in pretty much every episode, from nuclear meltdowns to organ failures. But he pulls through a remarkable number of times—even for a cartoon character!
Homer's luck is why Frank Grimes Jr. finds him so annoying. The inverse to Homer, Frank has had a life plagued by hardship and misery. After being hired at the power plant, he's struck by Homer's seemingly perfect life despite his laziness.
Grimes declares Homer his mortal enemy and basically has a mental breakdown. Considered one of the darker episodes of the show, Grimes's bad luck literally runs him into the ground.
7. "Bart of Darkness" (Season 6, Episode 1)
The Simpsons loves intertextual references, evidenced by its frequent modeling of scenes, gags, and entire episodes on classic or otherwise popular films.
"Bart of Darkness" is a brilliant example of this, inspired by the iconic Hitchcock thriller Rear Window. (The episode title itself refers to Joseph Conrad's famous 1899 novella Heart of Darkness.)
After the Simpson family decides to buy a swimming pool, Bart's dream summer is ruined when he breaks his leg. Now he's stuck in his bedroom, watching the whole town enjoy his pool without him.
But while Lisa is off becoming Miss Popular, Bart thinks he's witness to a murder at the Flanders house. Cast on, telescope out, Bart becomes a crazed recluse fixated on watching.
6. "The Mysterious Voyage of Homer" (Season 8, Episode 9)
Prepare to trip out on some funky 1960s psychedelia! During the annual chili cook-off, Homer flexes his threshold for spicy foods—even the glowing Guatemalan insanity peppers are no match for him once he's coated his mouth in wax to block the burn.
Homer swallows a bunch of them at once, causing wild hallucinations and a spiritual awakening. He meets his spirit guide in the form of a coyote, who makes him question whether Marge—currently mad at him—is really his soulmate.
As a result, Homer roams a vast desert that's littered with symbolic imagery and shifting objects. For a cartoon, this episode surprisingly explores some majorly deep metaphysical themes, taking us on a journey through the human psyche and into the soul.
5. "One Fish, Two Fish, Blow Fish, Blue Fish" (Season 2, Episode 11)
For all of Homer's near-death experiences, this one's certainly the most memorable. After accidentally eating a poisonous fish at a sushi restaurant, Homer is told he has only 22 hours to live.
Here, the show takes a serious tone as it moves away from comedic blunders and into heartfelt goodbyes.
With his last few hours on earth, Homer makes a list of things to do: listen to Lisa play her sax, make a tape for Maggie, plant a tree, make love, have one last beer. Homer's reconciliation with his father takes up far more time than he planned for, making him lose out on half the day.
He kisses his loved ones good night and weeps alone in an armchair. Even though we know he makes it through, we can't help but feel a little pang of sadness when his head drops down.
4. "A Streetcar Named Marge" (Season 4, Episode 2)
Another reference to a classic movie, "A Streetcar Named Marge" follows Marge as she auditions for a part in the local theater show.
Oh, Streetcar! is a musical production of A Streetcar Named Desire, where the role of Blanche is supposedly a "delicate flower being trampled by an uncouth lout." Feeling unappreciated by her family, the director witnesses Homer's lack of support and immediately casts Marge.
Parallel to this plotline is Maggie leading another classic movie re-enactment. While Marge is off rehearsing, Maggie is enrolled in a strict daycare center that prohibits pacifiers.
Maggie's iconic red pacifier is intrinsically linked to her character, almost like an extra limb. She goes to great lengths to claim it back, with an escape plan reminiscent of The Great Escape.
3. "Lisa's Substitute" (Season 2, Episode 19)
Prepare to shed more tears in season two's touching episode "Lisa's Substitute." Dustin Hoffman stars as the voice of Mr. Bergstrom, Lisa's new substitute teacher who steps in as a replacement father figure.
He's smart and understanding. He reads and cries and listens to what Lisa has to say. He has a sharp mind and a creative nature, qualities that Homer distinctly lacks but Lisa desperately seeks.
Of course, since he's a substitute teacher, Mr. Bergstrom eventually has to leave. After a mad dash to the train station, Mr. Bergstrom hands her a note to read whenever she feels alone.
It reads: "You are Lisa Simpson." (And this is the part where we try not to cry.) Though Homer and Lisa's relationship initially takes a toll, they are eventually brought back together again, closer than ever before.
For more heartfelt Homer-Lisa storylines, check out "Lost Our Lisa," "Lisa the Vegetarian," "Lisa's Pony," "Lisa the Greek," and "Lisa the Beauty Queen."
2. "Who Shot Mr. Burns?" (Season 6, Episode 25 and Season 7, Episode 1)
The only two-parter in all of The Simpsons, "Who Shot Mr. Burns?" ends season six on a cliffhanger and makes viewers wait for the seventh season's premiere to find out the culprit.
This animated take on the traditional whodunit murder mystery has the first part concluding with the supposed death of Springfield villain Mr. Burns, who's shot during a town meeting. Everybody has a motive and therefore everyone is a suspect.
These two episodes are iconic for one big reason: it was the first show to host a contest that married TV with the internet, prompting fans to call in and guess who the killer was.
Various conspiracy theories have even been put forward to suggest that the one shown to be the killer is, in fact, NOT the real killer!
1. "Homer the Heretic" (Season 4, Episode 3)
"Ah. I'm just a big, toasty cinnamon bun. I never want to leave this bed." I couldn't have put it better myself, Homer! My favorite episode of The Simpsons goes to an early one in season four, where Homer decides to quit church and start his own religion.
While Marge and the kids are freezing at church one early Sunday morning, Homer is sleeping at home, making his patented moon waffles, and dancing in his underwear like Tom Cruise in Risky Business.
Sometimes it takes a bad thing to make you appreciate the good. Homer's lazy Sunday is made pure bliss with the knowledge that he should be shivering through church. But after abandoning his faith, his lounging causes a house fire that almost leads to Homer's death.
Not only does Homer agree to give God another go, he meets the Big Man himself in a dream who tells him all about the meaning of life.
A Few More Honorable Mentions
There are just so many good episodes, I couldn't help but cap off this list with a few more honorable mentions:
- "Stark Raving Dad" (Season 3, Episode 1)
- "Deep Space Homer" (Season 5, Episode 15)
- "Homer the Great" (Season 6, Episode 12)
- "Home Sweet Homediddly-Dum-Doodily" (Season 7, Episode 3)
- "The Itchy & Scratchy & Poochie Show" (Season 8, Episode 14)