Legend has it that when Matt Groening was sitting in James L. Brooks’ waiting room, about to sell away his comic strip to become a TV show, he got cold feet about selling his life’s work and quickly scrawled a family with three kids and when he was called into Brooks’ office, he pitched this family for a TV show instead. That family, of course, became The Simpsons, one of the most beloved and groundbreaking TV series ever to hit the airwaves.
The show has been going on for so long that its steady decline in quality has now lasted for longer than the “golden age” did, but those early seasons contain some of the funniest material ever put on television.
10 King Size Homer (9.0)
Homer starts gaining weight more rapidly than usual when he realizes he’s just a few pounds away from qualifying for workers’ comp. Marge has reservations about Homer’s plan and he finds people’s attitudes toward him change.
With a lot to say about obesity, fat-shaming, and the ups and downs of working from home, “King Size Homer” is a primo Simpsons episode.
9 The Springfield Files (9.1)
Crossover episodes are usually a bad idea, but The Simpsons’ crossover with The X-Files was hugely satisfying for fans of both shows. Mulder and Scully travel to Springfield when Homer claims he saw an alien in the woods and nobody in town believes him.
From Scully forcing Homer to exercise to Mulder having a glamor shot on his federal identification, “The Springfield Files” does a terrific job of transplanting The X-Files’ characters into The Simpsons’ world.
8 The City Of New York Vs. Homer Simpson (9.1)
“The City of New York vs. Homer Simpson” is one of The Simpsons’ funniest episodes, but it, unfortunately, became retroactively controversial because Homer spends most of the episode at the World Trade Center. The episode aired in 1997 and was removed from syndication for a while in the wake of 9/11.
The animators painstakingly recreated Manhattan for the episode, which adds a visual supplement to timeless gags like the Khlav Kalash vendor and the “Checkin’ In” number from Kickin’ It: A Musical Journey Through the Betty Ford Center.
7 Marge Vs. The Monorail (9.1)
One of the common picks for The Simpsons’ best ever episode, “Marge vs. the Monorail” begins with Mr. Burns paying a huge fine to the town and Mayor Quimby holding a town meeting to determine what they’ll spend the money on. A snake oil salesman named Lyle Lanley pitches a monorail system and wows the town with a musical number.
However, Marge uncovers the history of Lanley’s monorail scams on the eve of the maiden voyage of Springfield’s monorail – conducted by none other than Homer.
6 Last Exit To Springfield (9.1)
Another regular pick for The Simpsons’ best episode, “Last Exit to Springfield” sees Homer elected the head of his workers’ union after Lisa is told she needs braces and Mr. Burns tries to cut his dental plan.
On top of mining a ton of absurd humor out of the premise of Homer leading a workers’ strike, “Last Exit to Springfield” has a lot to say about the balance of power between workers and their corporate overlords.
5 You Only Move Twice (9.2)
Homer uproots the family and moves them to a seemingly idyllic gated community when a supervillain offers him a job in “You Only Move Twice.”
Throughout the episode, the Simpsons are all driven to despise their new lives – all except for Homer, who loves his new boss (and is completely oblivious to his out-in-the-open global terrorism).
4 Who Shot Mr. Burns? Part One (9.2)
The sixth-season finale of The Simpsons set up the show’s first (and, so far, only) two-part episode. “Who Shot Mr. Burns? Part One” sets up beefs between various Springfieldians and Mr. Burns.
In the episode’s final moments, Mr. Burns is shot by an unseen assailant. Fans were left to ponder the titular question for months before the season 7 premiere paid it off.
3 Treehouse Of Horror V (9.2)
Since its second season, The Simpsons has delivered an annual Halloween special under the iconic “Treehouse of Horror” banner. These episodes are anthologies comprised of three spooky shorts and it’s very rare that all three are great, but “Treehouse of Horror V” manages it.
“The Shinning” puts Homer in Jack Torrance’s place in a Shining parody, “Time and Punishment” explores thought-provoking themes as Homer keeps unwittingly altering the course of history, and “Nightmare Cafeteria” plays like a regular episode that takes a dark turn into cannibalism.
2 Cape Feare (9.2)
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.
1 Homer’s Enemy (9.3)
One of The Simpsons’ most uncharacteristically dark episodes, “Homer’s Enemy” revolves around a hard-working self-made man who is hired to work at the nuclear plant and is subsequently astounded by the way Homer lives.
As an outsider who is driven out of his mind by the unbelievable world of Homer Simpson, Frank Grimes ranks alongside Hank Scorpio and Jessica Lovejoy as one of The Simpsons’ most memorable one-off characters.
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