10 Best Episodes of ‘The Simpsons’

Finding the standouts in a show with hundreds of episodes is a tall order, but certain stories keep coming up when you talk about the biggest moments in Springfield. These are the episodes that combined sharp writing, memorable gags, and clever storytelling into half hours fans still talk about, from union showdowns to space flights and mystery cliffhangers. You will find production credits, air dates, and key plot points so you can jump straight to the good stuff.

The entries below cover milestone ideas, famous guest voices, and formats that shaped how people remember the series. Each one includes the season and original air date, the writer and director, and the essential details that set the episode apart, like signature songs, parodies of well known films, or experimental structures that the show pulled off with ease.

Marge vs. the Monorail

Season 4, episode 12 first aired on January 14, 1993. Written by Conan O’Brien and directed by Rich Moore, it follows Springfield after the town receives a windfall and quickly buys a flashy mass transit system from salesman Lyle Lanley. Phil Hartman voices Lanley and Leonard Nimoy appears as himself during the inaugural run.

The story draws on the con man template popularized by ‘The Music Man’ and tracks the rushed construction, a doomed maiden voyage, and a last second repair from Homer. Scenes include the town hall song that sells the project and a control room sequence that explains how the monorail accelerates out of control before it is finally brought to a halt.

Last Exit to Springfield

Season 4, episode 17 first aired on March 11, 1993. Written by Jay Kogen and Wallace Wolodarsky and directed by Mark Kirkland, the episode centers on the nuclear plant union after Mr. Burns tries to cut dental benefits. Homer becomes union president to restore the plan while Lisa needs braces, which creates the conflict that drives the strike.

The episode includes a negotiation standoff in Burns’s office, a plant wide work stoppage, and a set of parody sequences that reference ‘How the Grinch Stole Christmas’ and other cultural touchstones. It also introduces Dr. Wolfe the dentist in a memorable chair side scene where Lisa learns what her braces will cost without the plan.

Homer at the Bat

Season 3, episode 17 first aired on February 20, 1992. Written by John Swartzwelder and directed by Jim Reardon, it covers the power plant softball season after Mr. Burns signs major league ringers to win a wager. The lineup features Wade Boggs, Jose Canseco, Roger Clemens, Ken Griffey Jr, Don Mattingly, Darryl Strawberry, Ozzie Smith, Steve Sax, and Mike Scioscia voicing themselves.

Each player meets an odd setback that sidelines them before the championship game, which puts Homer back at the plate with the bases loaded. He is hit by a pitch and forces in the winning run, which secures the title for the plant team and gives the episode its sports finale under Burns’s long list of eccentric managerial decisions.

Cape Feare

Season 5, episode 2 first aired on October 7, 1993. Written by Jon Vitti and directed by Rich Moore, it brings back Sideshow Bob after his parole hearing and sets him on a path to get revenge on Bart. The family enters the Witness Protection Program, takes the name Thompson, and moves to a houseboat for safety.

The plot mirrors ‘Cape Fear’ and ‘The Night of the Hunter’ with visual and musical nods, including an extended rake gag and a climactic performance of ‘H.M.S. Pinafore’ that delays Bob at a crucial moment. Kelsey Grammer returns as Bob and the episode details how the family is tracked to the boat and how Bart stalls for time until help arrives.

Treehouse of Horror V

Season 6, episode 6 first aired on October 30, 1994. Directed by Jim Reardon with segments written by several staff writers, the anthology includes The Shinning, Time and Punishment, and Nightmare Cafeteria. The frame presents three separate horror shorts rather than a single story.

The Shinning parodies ‘The Shining’ as the family caretakes an isolated lodge without television or beer. Time and Punishment follows Homer through a broken toaster that sends him across altered timelines. Nightmare Cafeteria shows students disappearing after school policies change in alarming ways, and the episode ends with a darkly comic curtain call.

Who Shot Mr. Burns? Part One

Season 6, episode 25 first aired on May 21, 1995. Written by Bill Oakley and Josh Weinstein and directed by Jeffrey Lynch, the story begins when Mr. Burns unveils a device that blocks the town’s sunlight. He is shot after tensions spike, which leaves Springfield hunting for a culprit.

Clues are scattered through scenes that implicate multiple residents while Chief Wiggum conducts the investigation. The mystery concludes in the season premiere that follows, where it is revealed that Maggie Simpson fired the shot during a confrontation over candy, and the town returns to normal once the sun blocker is dismantled.

You Only Move Twice

Season 8, episode 2 first aired on November 3, 1996. Written by John Swartzwelder and directed by Mike B. Anderson, the episode follows the family’s move to Cypress Creek after Homer accepts a job at Globex Corporation. His boss Hank Scorpio runs a secretive operation that turns out to be a full scale supervillain enterprise.

Albert Brooks voices Scorpio and delivers a stream of quick exchanges while Homer thrives at work. Meanwhile Marge struggles with an empty house, Lisa develops allergies to the local environment, and Bart is placed in a remedial class, which drives the decision to return to Springfield as Scorpio casually wins a showdown with government agents.

Lisa’s Substitute

Season 2, episode 19 first aired on April 25, 1991. Written by Jon Vitti and directed by Rich Moore, it introduces Mr. Bergstrom, an inspiring teacher who substitutes for Miss Hoover and encourages Lisa’s academic curiosity. Lisa forms a deep connection to him during a period of classroom changes.

Dustin Hoffman provides the guest voice under the credit name Sam Etic and shares several key scenes with Lisa, including a farewell at the station that ends with a hand written note. In the B story, Bart runs for class president against Martin Prince and learns how campaign tactics can shift a school election.

22 Short Films About Springfield

Season 7, episode 21 first aired on April 14, 1996. Directed by Jim Reardon and developed by Bill Oakley and Josh Weinstein, the episode presents a mosaic of quick stories from around town. Each segment focuses on different residents and many were written by different staff members.

The vignettes intersect in time and location and include a lunch at Skinner’s house that fans often call Steamed Hams, a ‘Pulp Fiction’ riff involving Chief Wiggum and Snake, and a comic mishap with a bee trapped in Smithers’s car. The structure allows the show to spotlight minor characters in short scenes that still connect to the larger setting.

Deep Space Homer

Season 5, episode 15 first aired on February 24, 1994. Written by David Mirkin and directed by Carlos Baeza, the story begins when NASA recruits an average American to boost public interest. Homer beats Barney for the slot and joins a shuttle crew after a chaotic training period.

The mission features floating ants after an ant farm breaks, a snack scene with potato chips in zero gravity, and a reentry scare that resolves with a safe landing. Media coverage includes an overexcited report from Kent Brockman and a celebratory salute for an inanimate carbon rod that briefly receives more credit than the crew.

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