5 “Burns’ Heir,” 1994
In case you ever questioned the lethal potential of a sponge, the opening scenes of “Burns’ Heir” should confirm your darkest fears. The most riveting part of this episode is getting to see Bart’s ID run amok with Burns’ pocket book. The episode also veers away from being overly sentimental while managing to be heartwarming. And the actors portraying the Simpsons (B’oh!) are hilariously bad. Fun fact: Homer’s quote, “Kids, you tried your best and you failed miserably. The lesson is never try,” has been annotated in the Oxford Dictionary of Quotations! Go back and watch this episode… It’s like kissing a peanut!
4 “The City of New York vs. Homer Simpson,” 1997
Yet another horrible victim of the designated driver system, Homer’s car winds up stranded in the heart of New York City. Like, smack-dab-in-the-middle. While the rest of the Simpsons relish their opportunity to see the sites of NYC, Homer deals with every indignant and incomprehensible character in the city. That’s a plus, though, because when else was he going to try crab juice? The scene where he runs to the bathroom (in successive towers) is hilarious as he witnesses another ticket being written. His escape from Manhattan will also leave you dying from laughter, if you can dodge that single gunshot.
3 “Homer’s Enemy,” 1996
The darkest Simpsons episode, “Homer’s Enemy,” provides a voice of reason that has no place in the show’s universe. Frank Grimes (or “Grimy” as he liked to be called) provides a brilliant, subversive foil to every aspect of Homer Simpson’s life — Grimes works hard, earns everything he gets (which isn’t much), and is not generally liked. So, when you put him next to Homer, it shows what a loveable boob Homer is in every aspect of his life. As Grimes puts it, “That incompetent oaf is in charge of our safety?” The results are hilarious. When Grimes goes insane at the end, he dies imitating Homer’s ignorance, a grim reminder of why we should all look out for high-voltage warnings.
2 “Kamp Krusty,” 1992
Like the moon landing, everyone remembers where they were when they first learned of Krusty's superfluous 3rd nipple. Any one who’s ever been away from their family in a less than hospitable circumstance will relate to this gem. Being the Simpsons, of course, the episode takes it to an absurd extreme — the campers don’t even eat gruel, but Krusty Brand Imitation Gruel. Oh well, 9 out of 10 orphans can’t tell the difference, anyway. One kid’s hat even got eaten by a bear (it was a nice hat). Krusty eventually makes it up to the woebegone campers by taking them to the happiest place on Earth: Tijuana!
1 “Homer Goes to College,” 1993
A love letter to your toga-wearing, Louie, Louie-playing, beer-guzzling college years. It’s just that Homer’s didn’t start until he was 38 with a wife and kids. Most of the humor from this episode stems from Homer’s misconceptions about college life, which he picks up after viewing The School of Hard Knockers. Especially his relationship with Dean Peterson (who used to be the bass player for the Pretenders), whom Homer eventually runs over with his car. Don’t worry, it was a prank. Homer also takes his nerdy roommates under his wing, teaching them how to spread mayhem in between nosebleeds. The perfect episode if you want to party down! Or if you’re S-M-R-T!
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