Now entering its 26th season, The Simpsons has earned the honor of the longest-running sitcom in America. Largely considered one of the greatest television series in history, the show has earned numerous accolades during its quarter-century tenure, including being named as the best television series of the 20th century by Time magazine. It’s also received 31 Primetime Emmies, and a Peabody Award.
Despite how long it’s been on the air, The Simpsons has managed to remain relevant within pop culture by actually parodying the human condition along with elements of society and culture in America.
With well over 500 episodes in existence, making any sort of “best of list” is a bit daunting. And, as anyone who has recently revisited the series on DVD, or for anyone who has been following FXX’s 12 day marathon (FXX is included with some cable packages, and if you have DirecTV there’s a free trial going on right now that includes the channel) it can be difficult to pinpoint the all-time best — yet a few do stand out among others.
1. “Treehouse of Horror”
Originally entitled “The Simpsons Halloween Special” this episode premiered as the third episode within the second season of the show. Inspired by horror comics of the 1950’s, it was preceded by a disclaimer that it might actually be too frightening for children to watch. “Treehouse of Horror” would become the first of many other themed Simpsons episodes (and the first of other “Treehouse of Horror” incarnations). During the show, the Simpson children recant three scary stories while in the family treehouse, and James Earl Jones even makes a surprise appearance, offering his recitation of Edgar Allan Poe’s “The Raven.” With a viewership of over 14.6 million households, “Treehouse of Horror” was well received by both critics and viewers.
2. “22 Short Films About Springfield”
Aired as the 21st episode of the show’s seventh season, “22 Short Films About Springfield” gave viewers a closer look into the lives of the hapless denizens of Springfield. A series of interrelated stories and skits are prompted by Bart wondering whether or not Springfield’s folks have ever have anything interesting happen in their lives. In many ways, the episode loosely parodied Pulp Fiction and even provided the impetus for a possible spin-off of the show. Phil Hartman guest-starred in the episode.
3. “Bart Sells His Soul”
Aired during the fourth season of The Simpsons, “Bart Sells His Soul” begins when Bart sets out to prove that souls do not actually exist after he gets caught during a prank at church. Despite the fact that Lisa warns him against it, Bart “sells” his soul for $5 to Milhouse by simply giving him a slip of paper. Soon, he begins to experience some strange changes and comes to believe that he actually has sold his soul. Lisa eventually managed to get it back for him, much to his relief. This episode also contains what some consider Bart’s most infamous line: “I am familiar with the works of Pablo Neruda.”
4. “Flaming Moe’s”
First aired on November 21, 1991, “Flaming Moe’s” begins when Homer lets Moe Szyslak in on his secret alcoholic cough medicine recipe. When Moe steals the recipe and it becomes a smash hit at his bar, trouble arises and Homer plots his revenge. This episode is unique because it was the first to give oddball bartender Moe a larger role beyond just that of the neighborhood liquor purveyor. While Moe’s Tavern is loosely based on a bar located in Los Angeles, it also closely parodies the beloved sitcom Cheers. A character in this episode is reminiscent of Shelley Long’s “Diane Chambers” character from the television series, and Aerosmith also makes a brief cameo, the first band to appear on the show.
5. “Lisa The Vegetarian”
Lisa The Vegetarian aired during the show’s seventh season. When Lisa decides to stop eating meat after making friends with a lamb from a petting zoo, she is ridiculed by everyone in her family and at school. But luckily she manages to maintain her commitment to vegetarianism with a little help from Paul and Linda McCartney. More than 14 million viewers tuned in for the episode, which earned a Genesis Award and an Environmental Media Award.
Honorable Mention “Marge Vs. The Monorail”
No list would be complete without the classic 1993 episode Marge Vs. The Monorail. Even Conan O’Brien says this is his favorite among the four Simpsons episodes that he wrote. The town received a windfall $3 million dollars from a fine due to Mr. Burns’ illegal disposal of nuclear waste. The townspeople decide to spend money on a needless monorail… and only Marge seems to notice it’s built from shoddy materials. The monorail gets christened by none other than Star Trek’s Leonard Nimoy.
Now that we have picked our top 5 (well, six, because we cheated and snuck in an honorable mention), we have dissed 494-plus other episodes, including your favorite. Let us know what episode we missed, and which are your favorites…