Top 10 Simpsons Episodes of All Time

10. The Boy Who Knew Too Much, May 5, 1994

In one of the last episodes of the show’s Bart focus, the episode shows Bart Simpson as he struggles with a moral dilemma: should he save an innocent man from jail or avoid Principal Skinner’s wrath?

The episode’s strength lies in making viewers sympathize with Bart and his ordeal all through the story. Viewers support and cheer Bart as he skips school when it’s at its most oppressive, fear for him while Principal Skinner doggedly pursues him, and agonize over whether he should do the right thing despite the punishment.

To balance the tension, the episode throws in great gags, like the French waiter’s slapstick clumsiness, turns court process inside out, and makes annoyingly obnoxious characters like Freddy Quimby delightful. And of all the times Bart and Skinner have butted heads, this may be the best, as never does Principal Skinner come across as formidable an enemy as this episode.

Best Moment- Principal Skinner chasing Bart all the way across town, up cliffs and through rivers, to catch him at hooky.

Best Line- Homer Simpson: “I’m only doing what I think is right. I believe Freddy Quimby should walk out of here a free hotel.”

9. Lisa on Ice, November 13, 1994

As Lisa discovers a natural talent for goaltending, she gains a never-before-seen bloodlust. This episode is full of the bloodlust that hockey inspires, even in kids’ hockey. At every game are devoted fans of Bart and Lisa who scream for blood and pain, and even Marge gets drawn in. In the end, when Bart and Lisa make up, Homer decries both kids as losers, and the crowd breaks out in riots.

In the early seasons, The Simpsons always carried out its social commentary subtly. This episode is a classic example, showing how parents get overinvolved in kids’ sports, and in doing so suck the fun out of the game, replacing it with hatred. It stops from being heavy-handed because the focus is on Bart and Lisa’s conflict. In a perfect image, the final shot is Bart and Lisa embracing while soft music plays in the background, with half the arena aflame from the rioting.

Best Moment- Homer attempts to chomp his way toward a pie, but hits his head on the shelf.

Best Line- Ralph Wiggum: “Me fail English? That’s unpossible.”

8. Rosebud, October 21, 1993

One of comedy’s great villains is Mr. Burns, the wealthy miser who owns Homer’s workplace and wields tremendous power and influence. Much of his character is borrowed from Citizen Kane. This episode drives the tribute home and manages to analyze the film character too. It asks the question: what would Charles Foster Kane do if he could relive the childhood innocence he craved so much?

The episode is about Mr. Burns’ search for his long-lost teddy bear, which is found by the Simpsons, and claimed by Maggie. As a result, viewers see Homer at his best as he turns down massive wealth and withstands the wrath of the town out of love for his baby daughter, since Maggie herself falls in love with the bear. Current episodes of The Simpsons try to make Homer into a monster, along with Mr. Burns, but great episodes make them sympathetic.

Best Moment- The sci-fi ending, with Mr. Burns and Waylon Smithers as robots.

Best Line- Mr. Burns: “Smithers, have the Rolling Stones killed!”

7. Marge vs. The Monorail, January 14, 1993

Phil Hartman’s tragic death left a hole in The Simpsons that has never been filled. His two characters, washed-up Troy McClure and inept attorney Lionel Hutz, were important parts of the early seasons’ humor. But perhaps his best performance was his one-time gig as Lyle Lanley, the corrupt businessman who sold Springfield a monorail.

Marge’s best moment comes in this episode, as the voice of reason not to just her family, but to the entire town as it gets swept up in monorail fever. She even goes on a quest to find the truth about the monorail, and in doing so, manages to help save the day when the monorail goes haywire.

The episode does best what so many others don’t do as well: make the entire town of Springfield a character. The town has formed into mobs from time to time, but rarely unites to screw up spectacularly and collectively like they do here. Best of all, the guest voices are superb, topped by Leonard Nimoy, who has all of six lines, each of them hilarious.

Best Moment- The town breaking into the ‘Monorail’ song.

Best Line- Homer: “Donuts, is there anything they can’t do?”

6. The Otto Show, April 23, 1992

One of the secondary characters got his only moment in the sun when Otto, the bus driver, loses his license and has to get it back. Viewers see his friendship with Bart blossom, and better yet, his enmity with Homer grow. Even though Otto is a born slacker with low expectations of life, the audience can’t help but cheer when he gets back his license the only possible way, unfairly.

The sidebar plot is also unforgettable, as Bart sees metafictional band Spinal Tap in concert and decides to take up electric guitar. When he gives up at the end, Homer gives him a reassuring pep talk by saying that failure is okay after minimal effort. He then suggests they watch TV, and what’s on? “It doesn’t matter.”

Best Moment- Otto destroying Springfield as he drives the kids to school late.

Best Line- Otto: “Wow, I’ve never been called me an adult before. I’ve been tried as one but…”

5. Homer the Great, January 8, 1995

Who knows of a television episode where the characters sing a song, and that song becomes a popular drinking song ever since? We do, we do. When Homer joins the Stonecutters, he sings their songs, enjoys their privileges, earns their hatred, and then their devotion.

What starts out as a club turns into absolute hilarity with some of the best one-liners ever written. Partly a parody of the Freemasons, partly a parody of various celebrities and a good look at cliquishness in all ages, this episode looks deep into the hearts of viewers and assigns them numbers based on the order in which they watched.

Best Moment- The Stonecutter song

Best Line- Number 1: “Welcome to the Stonecutters, No. 912, who since the dawn of time have split the rock of ignorance to let the light of knowledge and truth shine through. Now let’s all get drunk and play ping-pong!”

4. The Last Temptation of Homer, December 9, 1993

Despite Homer’s vicious eating, his shirking responsibility, he has always been faithful to Marge, and loved her the best way that he can, even if he’s far from a good husband. But this time, he had to face a serious test. Along came Mindy Simmons, a woman not only beautiful but who shares every possible personality trait with him.

The two end up alone together in increasingly contrived situations, and Homer seriously considers cheating on his wife. Only at the end do we see what Homer’s love is really made of, and after everything, the viewer loves Homer that much more.

Best Moment: Homer imagining Barney Gumble in a bikini.Of course, the episode might be the funniest of the entire series, with its zany one-liners, Bart as a nerd, and reality-bending the way only The Simpsons does best.

Best Line- Homer: “Oh Margie, you came and you found me a turkey, on my vacation away from workey.”

3. You Only Move Twice, November 3, 1996

Being the latest airdate on this list, this episode could be considered the last truly great episode of The Simpsons. It earns this stature because of its guest character, the unforgettable Hank Scorpio, the kind-hearted, fun-loving industrialist who happens to be a supervillain. The character, voiced by Albert Brooks, sadly makes his only appearance on the show. As the boss everyone wants to have, and a villain who puts Blofeld to shame, he could very well have starred in his own series.

The episode turns the Bond villain pantheon inside-out, and even takes a shot at the Denver Broncos, only a year and a half before their first Super Bowl. Viewers finally see Homer being good at his job and happy, but the rest of the family are not, so The Simpsons don’t stay in their new town, and leave just as Scorpio begins his first major step in world domination.

Best Moment- Scorpio threatens a stupidly skeptical UN with violence.

Best Line- Scorpio: “Homer, if you could kill someone on your way out, it’d really help me.”

2. Last Exit to Springfield, March 11, 1993

Probably the funniest and most quotable episode of The Simpsons, one that every fan must be required to recite verbatim, according to Entertainment Weekly. To pick out any particular aspects or segments would be to negate the overall effect of the episode. Suffice it to say that Homer Simpson has no business being the head of the union, and he knows it better than anyone.

The episode also makes fun at a trope then overused in comedy, where a character plays back things he’d recently heard a few times in order to form a conclusion about his own situation. In this case, because Homer was so stupid, the internal playback was stretched out, and thus was born the overly long gag. So fans tired of this joke in Family Guy can blame this episode for it. Then watch it again, and see how it can be done perfectly.

Best Moment- Lisa's dental operation sequence.

Best Line- Grandpa Simpson: “The important thing was that I had an onion tied to my belt, which was the style at the time.”

1. Cape Feare, October 7, 1993

No episode on any TV show manages to marry drama, comedy and suspense like this episode. Sideshow Bob, voiced by Kelsey Grammer, makes his third appearance and turns his evil genius toward killing Bart Simpson. As Bob prepares and gets closer to ending Bart, the audience shudders with fear at this madman. Then they laugh out loud at one of the great one-liners or Bob’s painful abuse in the episode.

Some of the funniest slapstick made its appearance in this episode, as Sideshow Bob got twelve rakes, hot coffee, speed bumps, a cactus patch and a parade of elephants in his face. The Simpsons run, but they cannot hide from Sideshow Bob’s revenge, and so viewers get a nail-biter, abetted by a chilling score, as Bart has to overcome this grave threat to his life only by outwitting his enemy.

For its jaw-dropping suspense, terrifying villain and outrageous humor, this episode will be remembered as a television classic, even though Sideshow Bob has been overused ever since and comes up with evil plots as filler episodes.

Best Moment- Homer getting grilled by the FBI on his new identity.

Best Line- Homer: “Hey Bart! Want to see my new chainsaw and hockey mask?!”