You don’t just become one of the longest running animated series in the land without great content. The Simpsons has been at it since the late 1980s, delighting viewers with its hilarious depiction of life in suburban America.
They say Frasier was the smartest show on television and Seinfeld was great in that it was often about nothing at all. The Simpsons‘ success can be pinned on its core family of five characters, so unique yet complementary. Homer is the well-meaning doofus; Marge the housewife with a deceptively dynamic personality. Bart is the daredevil and troublemaker, while Lisa is bookish and brilliant. Maggie, well, she mainly just crawls about. Together, they form a relatable unit that’s prone to all kinds of hilarity, near disasters, and heartwarming good.
Of course, it’s about more than just the family of five on Evergreen Terrace. Countless other characters shine brightly, from surly barkeep Moe to wealthy elder statesman and nuclear power plant owner Montgomery Burns. There’s the wit of Sideshow Bob, the drunken bliss of Barney Gumble, the sloppy know-it-all-ness of Comic Book Guy, the incessant laugh of Dr. Hibbert, the chain smoking and constant smirks of sisters Patty and Selma. It’s no wonder celebrities have lined up for years to be featured in an episode. It’s also unsurprising that entire online encyclopedias are devoted to the show.
In the first dozen seasons, especially, The Simpsons offered brilliant storylines injected with extremely clever humor. There’s tons of entertaining parallel action and most episodes deliver a lesson or two, creatively and comically. Just a few talented people created voices for an entire Springfield community, which is based in Oregon for those still wondering (creator Matt Groening is from Portland plus there are clues that eliminate the possibility of any other state).
Here are some of the greatest episodes pulled from one of the greatest ever television series:
Conan O’Brien wrote a relatively small number of episodes of the show, but they’re all universally fantastic. This one is his best and his last, full of one-liners and collegiate tomfoolery. The references are subtle and smart, with shout-outs to movies like Animal House and shows like Star Trek.
This episode from the stellar sixth season sees the Simpson clan head to a theme park named after the two brutally violent characters featured on Bart and Lisa’s favorite TV show, hosted by Krusty the Clown. It’s a spoof on Disneyland, with the park’s animatronic hosts ultimately turning on their guests. It also offers one of the funniest brief scenes in the show’s history.
The two major plotlines in this amazing episode involve Lisa cheating on a test and Homer raising a pet lobster named Pinchy. Lisa learns some humility and becomes briefly addicted to video games while Homer becomes so close to his crustacean that it becomes a member of the family. The Simpsons even manage to piss off the Catholic church in this laugh-out-loud episode.
A thoughtful parody of James Bond culture, “You Only Move Twice” sees the Simpson family pack up for Cypress Creek, a seemingly perfect development where Homer takes his dream job. Alas, it doesn’t go according to plan, with Marge taking to day drinking while living in a self-cleaning house and Homer realizing his new boss, the unrivaled Hank Scorpio, is a supervillain. There’s even an ongoing reference to HAL 9000 from Kubrick’s genius 2001: A Space Odyssey.
A major highlight of season 12, this episode functions like a musical. Homer somehow lands a job as monorail conductor, clad in a cape no less. An unsung hero of a character is undoubtedly Lyle Lanley, an old time-y conman voiced by the incredible Phil Hartman. Another Conan O’Brien joint, this episode even features a pop-in by Leonard Nimoy.
One of the fist episodes to pack in a full serving of celebrity cameos, “Homer at Bat” sees the nuclear power plant’s recreational softball team injected with a much of ringers from the big leagues. Featuring Ken Griffey Jr., Jose Canseco, Darryl Strawberry, and more, it’s entertaining from start to end and showcases Mr. Burns as a hilariously antiquated baseball coach.
You may be catching on to the theme here that if Homer is at the forefront of an episode, generally comic gold ensues. This trip-y chapter sees Mr. Simpson eat a mysterious pepper in a local chili cook-off before hallucinating and hanging out with the likes of dessert turtles and a coyote voiced by Johnny Cash. Homer’s gut-first approach to life is on full display here.
The last episode of the seventh season, the story here involves a family trek to the beach. Always eager to exploit the generosity of neighbor Ned Flanders, the Simpsons use his house on the coast for a getaway. There, Lisa aims for a new, cooler persona while Bart gets envious. Ever sharp, the episode features nods to classic films like American Graffiti and Adventures in Wonderland, among others.
This episode puts the Bart vs. Sideshow Bob feud on a pedestal. It’s a parody of the movie it’s named after and includes some great homages to Alfred Hitchcock. The densely packed episode features everything from electric eels and a witness protection program to sex changes and Kelsey Grammer’s theatrical prowess as the voice of Bob. And it all somehow works perfectly together.
If you only watch a single season, the fifth might be it. This feel-good episode comes from that storied year, with guest appearances by David Crosby and George Harrison on top of a remarkably good Springfield quartet led by Homer called the Be Sharps. The episode has it all, from incredibly performances by the likes of Kwik-E-Mart owner Apu to a hysterical scene at Moe’s Tavern featuring Yoko Ono.
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