5 Best Simpsons Episodes Ever

What’s your favorite?

This Sunday, Matt Groening’s The Simpsons will air its 500th episode—a television milestone that’s never been replicated by any other scripted television sitcom. Like many people, The Simpsons has truly been an integral part of my life. I was 11 years old when the first episode aired on December 17, 1989. (Though true fanatics should note that I was eight for the first airing of the sketch during The Tracey Ullman Show on April 19, 1987.) My grade school quickly banned any and all Simpsons paraphernalia, thanks to t-shirts emblazoned with “I’m Bart Simpson. Who the hell are you?” My parents, at first, did not allow us to watch it (just like the other FOX bastion of bad taste, Married… with Children). But, somehow—mostly through watching a friends’ houses—I saw every episode. Though recent seasons (“Worst. Episode. Ever.”) will never compare to its genius beginning, it still remains immensely influential and a true must-see TV every Sunday.

So in honor of the 500th episode, here are my choices for the five best episodes of all time.

5. I Love Lisa
Season 4, Episode 15

An episode that is both immensely touching and hysterically funny. But the real reason I love this episode is because it features my favorite character, Ralph Wiggum. Best line: “The doctor said I wouldn’t have so many nose bleeds if I kept my finger outta there.”

4. Homer’s Phobia
Season 8, Episode 15

After learning that their new friend John (John Waters) is gay, Homer flips out. Worrying that Bart might be gay, Homer tries to make Bart more masculine: staring at billboards with scantily dressed women and visiting a steel mill. But after John saves Bart and Homer from vicious reindeer (seriously), Homer overcomes his fear. Best line(s): “I like my beer cold, my TV loud, and my homosexuals fuh-laaaaaming.” “He didn’t give you gay, did he?”

3. Treehouse of Horror
Season 2, Episode 3

While Treehouse of Horror V (season six, episode six) is probably the best of the Treehouse episodes, but the first started it all. It featured the independent stories based on haunted houses, alien abductions, and Edgar Allan Poe’s The Raven. It began a new Halloween tradition. Best line(s): “It chose to destroy itself rather than live with us. You can’t help but feel a little rejected.”

2. Marge vs. The Monorail
Season 4, Episode 12

When Mr. Burns is fined $3 million for dumping nuclear waste in the park, a slick salesman, Lyle Lanley (Phil Hartman) convinces the town to build a monorail. The genius of this episode, a take on The Music Man, is in the perfect writing, the brilliant song spoofs, and a cameo by Leonard Nimoy. Best line(s):Marge: Homer, there’s a family of opossums in here! Homer: I call the big one Bitey.”

1. Cape Feare
Season 5, Episode 2

After Sideshow Bob (Kelsey Grammer)—who has sworn to kill Bart Simpson—is paroled, the Simpsons enter the witness relocation program and move to Terror Lake. The episode encapsulates the best of the entire series: parody of well known pop culture, sight gags (Bob stepping on rake after rake), brilliant guest performances, and wonderful randomness (Bob performing the score to H.M.S. Pinafore). Best line(s): “Oh my god! Someone’s trying to kill me! Oh wait. It’s for Bart.” “All right, this next song is dedicated to Bart Simpson with the message ‘I am coming to kill you slowly and painfully.’”

Honorable Mentions: Das Bus (Season 9, Episode 14), The Blunder Years (Season 13, Episode 5), and Mr. Plow (Season 4, Episode 9)


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