I have been a fan of The Simpsons since nearly day 1. I’m such a fan that I have tattoos inspired by the colorful world of weird yellow people. I eat, sleep, breath, and quote Homer on a daily basis. I can relate closest to Lisa. My favorite supporting character is Moe and his constant anger and depression. My favorite minor character is Gil Gunderson, the always failing hard-on-his-luck salesman. But what if you aren’t a fan already? What if you want to find out just why The Simpsons is a culture phenomenon and you are overwhelmed by all 596 episodes? Well, here’s where a long-time fan recommends you start. These aren’t the best overall episodes – though they are all great – rather, these are the best episodes to jump into the series.
1. LISA’S SUBSTITUTE (Season 2, Episode 19)
This is an early episode. As a result, this has fewer gags and more story than most on our list. It also has fewer obscure supporting characters and zany hijinks. This makes it perfect for someone trying to understand what makes these characters special. Though Homer and Bart get all the merchandise, it’s Lisa that really becomes the heart of the show. The ending note given to Lisa by her substitute, Mr. Bergstrom (voiced by Dustin Hoffman, no less), is the second most touching moment in the series to date.
2. HOMER’S ENEMY (Season 8, Episode 23)
Frank Grimes (voiced by William H. Macy) is your typical down-on-his-luck character you’d find in almost every Arthur Miller play. But this is the world of the Simpsons. So, this hard luck case that would be the hero in his own story ends up the villain in Homer’s. It’s a perfect jumping on point for those who think Homer is just an idiot and the Simpsons doesn’t understand itself. You can laugh at the absurdity of the very idea of the well-meaning buffoon trope.
3. TWENTY-TWO SHORT FILMS ABOUT SPRINGFIELD (Season 7, Episode 21)
Rather than a coherent story focused on the family, this episode masterfully takes a look at the crazy supporting characters in the Simpsons’ world. This is crucial to understanding what makes the show great because no other show has been able to have hundreds of minor characters with fleshed out personalities quite the way Matt Groening’s creation has. Oh, and it parodies Pulp Fiction. Who doesn’t love Pulp Fiction?!
4. TREEHOUSE OF HORROR (Various Seasons)
This entry is a copout because I am including every Treehouse of Horror Episode (though Treehouse of Horror V is the best). These episodes are wildly inconsistent but still great fun. Marathon a few of them that parody your favorite films. You don’t need to know anything other than the basic premise of the show to enjoy these episodes and they are always good for a few laughs. As a bonus, this is a great thing to marathon on the background of a party.
5. THE SEEMINGLY NEVER-ENDING STORY (Season 17, Episode 13)
Far and away one of the best episodes from the dark days of the late teens season, this shows what these writers and characters are best at while managing to snag an Emmy. The main story is a story-within-a-story-within-a-story and so on, all being told from a jumbled memory. It’s basically utter nonsense that’s both hilarious and at times smarter than any other sitcom could be.
6. A MILHOUSE DIVIDED (Season 8, Episode 6)
Some people don’t seem to like this episode because it is admittedly kind of depression. But it’s also absolutely hilarious. It’s one of my favorite episodes from my favorite season, and it masterfully captures the feel of love, divorce, and the inability to draw dignity. A great episode to pick you up when you’re feeling down, while still reveling in the things that make us sad.
7. AND MAGGIE MAKES THREE (Season 6, Episode 13)
This is arguable the best episode of the entire series. It’s at times both hilariously fun and deeply poignant in ways that no other show on television could be. It’s also a great episode for understanding the family dynamics, and why Marge would ever stay with Homer. The closing moments of this show also always tear me up, no question about it. Oh, and it has Knight Boat, the crime solving boat!