The Simpsons: Everything You Need to Know

Escaping the grasp of The Simpsons is fairly impossible in the modern age.

Jaiden Moreno

Escaping the grasp of The Simpsons is fairly impossible in the modern age.

It would be hard these days to find somebody who has not heard of The Simpsons. The animated sitcom is the longest-running primetime television show in history, and it has dominated American pop culture since the early ’90s. The show follows the everyday lives of the Simpson family living in the fictional city of Springfield. Homer, Marge, Bart, Lisa, and the many, many other characters who populate Springfield are some of the most instantly recognizable faces in television, and after three decades, they’re still going strong without showing signs of ending.

Diving into the world of The Simpsons can be a daunting task; with over 32 seasons and 706 episodes under its belt, starting this cartoon certainly feels overwhelming. So, if you are new to the show and do not know where to begin watching, or even if you just want to figure out if the show is for you, here are the six perfect episodes to start with. Thankfully, since The Simpsons exists in a cartoon world and none of the characters age, it is not necessary to watch the show in order.

“Marge vs. the Monorail” (Season 4, Episode 12): The Simpsons, in my opinion, picked up in its fourth season. While cases could be made for many episodes as the bringer of the show’s golden age, I would argue that the true winner is “Marge vs. the Monorail.” This is one of the most famous episodes of the show, and for good reason—it is absolutely hilarious. The plot follows the citizens of Springfield trying to decide what to do with a recently acquired sum of three million dollars. When a Music Man-style salesman named Lyle Lanley shows up with the promise of building a Springfield monorail, nearly everyone is immediately swept up in the excitement. Construction of the monorail quickly begins, but someone notices that things are not exactly what they seem. That character is Marge Simpson. Each character is at the top of his/her game here, with nearly every supporting character getting a standout moment. The episode culminates with the monorail’s maiden voyage, where the machine inevitably flies out of control. Homer is the monorail conductor, of course, and he must quickly find a way to shut it down before it flies off the tracks. It’s a ridiculous final act, but the sheer number of jokes thrown at you at once will keep you busy with laughter the entire time.

“Last Exit to Springfield” (Season 4, Episode 17): Some of the greatest episodes of The Simpsons focus on Homer’s job at the town’s nuclear power plant, but none are as funny as “Last Exit to Springfield,” an episode dedicated to Springfield’s resident supervillain: Mr. Burns. Charles Montgomery “Monty” Burns, the 104-year-old owner of the power plant, eliminates the dental plan from the company contract, leading to the workers to go on strike with Homer as their leader. The episode has some of the most infamous gags in the show’s history (If you have seen the “Dental plan, Lisa Needs Braces” memes that swarm the internet, it is from this episode), but it’s also the best showcase for Mr. Burns, who is one of the funniest supporting characters on the show. While he is often portrayed as nothing more than an incompetent old man, Mr. Burns is a formidable opponent to Homer in this episode, even embodying the Grinch himself in one key scene.

“Treehouse of Horror IV” (Season 5, Episode 4): One of the mainstays of The Simpsons throughout its 30-plus years on the air is its annual “Treehouse of Horror” specials. Once a year, the writers of the show let themselves loose and create one non-canon episode with the three craziest Halloween stories that they can come up with. And while you could make a case for many “Treehouse of Horror” specials being the best, (I particularly like V, if only for the parody of The Shining), “Treehouse of Horror IV “is the true highlight. It delivers three of the funniest segments in the history of this Halloween tradition. The first segment, “The Devil and Homer Simpson,” features Homer being put on trial by the devil after he sells his soul for a donut. Naturally, the devil is none other than Ned Flanders, Homer’s jolly, religious neighbor. The second segment, “Nightmare at 5 ½ Feet,” is a parody of the classic Twilight Zone episode “Nightmare at 20,000 Feet,” where Bart keeps seeing a gremlin on the side of his school bus. The greatest delight might be the final segment, “Bart Simpson’s Dracula,” which features Bart and Lisa trying to kill a vampiric Mr. Burns.

“Homie the Clown” (Season 6, Episode 15): Another classic Simpson trope is the common episode storyline of Homer or Marge getting some wacky new job. The funniest of these episodes is season six’s “Homie the Clown,” where Homer becomes a fill-in for Krusty the Clown himself. Krusty is the star of a famous children’s television show in Springfield and is Bart’s personal idol. After Homer sees a billboard for a Krusty Clown College, he quits his job and becomes a Krusty impersonator for a living. While the plot is fairly simple for an episode of The Simpsons, “Homie the Clown” exceeds by having possibly the highest laugh-per-minute ratio of any episode from the show. The jokes come fast and loud, from Homer’s imaginary clown-family to Krusty attacking his clown college graduates with a joy buzzer.

“Who Shot Mr. Burns?” Parts 1 & 2 (Season 6, Episode 25 & Season 7, Episode 1): “Who Shot Mr. Burns?” was The Simpsons’ first ever two-part episode. As the title would suggest, the episode(s) are a Simpsons whodunnit, where everybody in the town is a suspect. Thanks to Mr. Burns stealing oil from the elementary school, closing down Moe’s Tavern, and building a giant metal circle to block out the sun, everybody in the town is ready to kill Mr. Burns. So, when he gets shot in the center of town square, it is soon up to the bumbling Chief Wiggum to solve the mystery. “Who Shot Mr. Burns” is a great episode for many reasons, but its best attribute is the genuinely surprising mystery at its core. The first episode leaves many clues throughout its story, giving you the steps to figure out who really shot Mr. Burns. If you are going to watch the episode, don’t look it up beforehand; you will want to be surprised by the end.

“The Summer of 4 Ft. 2” (Season 7, Episode 25): Lisa Simpson is the heart of The Simpsons, and it is no surprise that some of the show’s sweetest episodes are centered around her. In the season-seven finale “The Summer of 4 Ft. 2,” the family gets to stay at Ned’s beach house for a week. Lisa, tired of being an unpopular geek at her school, decides to reinvent herself as an entirely new person during this vacation. She quickly makes herself a group of friends in the beach town, but a jealous Bart sets out to ruin the new friendships. Homer delivers plenty of laughs throughout the episode, most of which stem from his battles with Ned’s septic tank, but the best part of “The Summer of 4 Ft. 2” is how surprisingly sweet it is. For a show that is nearly always pure comedy, it is nice to get an episode that tells a happy story about a family that loves each other.

If you have decided that you want to invest in watching The Simpsons, a core part of today’s pop-culture, there are two possible routes you could take to watch it. You could either just jump around, picking random episodes to watch (as I did when I first started watching it), or you could simply start watching it straight through. If you choose the latter option, I recommend skipping the first three seasons and starting with season four. There are some great episodes in these first seasons (“Krusty Gets Busted,” “Homer at the Bat,” “Black Widower,” and “Lisa’s Substitute” are all standouts), but the show really starts to pick up by season four. Seasons 4-8 are pretty much golden age territory, and while by season nine there is certainly a decline in quality, the show is always quite funny and is never unwatchable. However, if you choose to watch the show, you will almost certainly enjoy the experience. The Simpsons has been on for 32 years for a reason: it is really, really funny and no other show exists quite like it.