I have a really good friend who’s my age who never watched The Simpsons growing up. Her reasoning is because her mom thought it was a bad influence (even though she tells me that she was allowed to watch Unsolved Mysteries all the time). Now, I get it. I watched The Simpsons episodes growing up from the very beginning with “Santa’s Little Helper” when I was only seven. Hell, I even watched The Simpsons shorts on The Tracey Ullman Show (Remember that?). So, I saw tons of instances where Homer strangled his son and Bart disrespected his parents, and I grew up okay! I think.
But anyway, one day, after she was telling me that she’s watched Schitt’s Creek for the millionth time, I told her that maybe she should give The Simpsons a try. She’s cool, so she said that she would watch it, but she wanted to start from the very beginning. So, I was like, “Hold up. There are like, 600 episodes (there are actually 703), and that’s way too daunting.” And I then I thought, well, some of the first season is kind of rough, and she might not like it. So, I ultimately decided to come up with this list of 10 great episodes of The Simpsons for people who are new to the show.
I was tempted to be like most fans and say, “Don’t watch anything past Season 10.” But as somebody who has actually watched all 703 episodes, I thought that I would include some of the later stuff, too. Because honestly, some of the later stuff is really good! So, here they are. The ten best episodes (All of which can be found on Disney+) to check out if you've never watched The Simpsons before. Aye, caramba!
“Oh, Brother, Where Art Thou?” (Season 2, Episode 15)
There are some great episodes in Season 1, but I think Season 2 is when the series really hit its stride. I was tempted to pick “The Way We Was” since that’s a sweet episode, but I decided on “Oh, Brother, Where Are Thou?” since it’s one of the funniest episodes of the entire series. Homer meets his long-lost half-brother, Herb (voiced by Danny DeVito) who happens to be a millionaire. Well, since they’ve been estranged for so long, Herb has no idea what a dimwit Homer is, and he allows him to design a new car that his company will sell. Homer takes on the task with gusto! ... And hilarious results.
I actually have a replica of the car (aptly titled “The Homer”) in my basement. It’s a hideous creation, with TWO bubble domes (one for the driver, and one for the kids), but it also predicted giant cup holders, which cars have had for years now. This is a great episode to start with since it has that trademark humor, but also that sweetness that the show is occasionally known for with the relationship between Herb and Homer. Most importantly though is that it has that pop at the end with the actual reveal, which is still hilarious, even today.
“Homer at Bat” (Season 3, Episode 16)
In this legendary episode that features the voice talents of (are you ready for this?) Steve Sax, Wade Boggs, Ozzie Smith, Roger Clemens, Don Mattingly, Darryl Strawberry, Ken Griffey Jr., Jose Canseco, and Mike Scioscia, Nuclear Power Plant boss, Mr. Burns, puts together an all-star softball team to win a bet against his rival, Aristotle Amadopolis from Shelbyville. But something weird happens to each of the players, so Homer ends up being the star. It’s a very weird and very wonderful episode.
I’m picking this episode on the off-chance that you might have been a baseball fan growing up, but also because this episode shows just how much star power the show has garnered over the years. The bizarre way that each player misses the game is also classic Simpsons zaniness that you wouldn’t find on any other show. And for any cartoon that did try to replicate this kind of weird storytelling, well, as they say on South Park, “The Simpsons did it first.”
“Selma’s Choice” (Season 4, Episode 13)
One common question that a lot of people around my age have is whether they should have kids or not. Well, in this episode in the fourth season, Marge’s sister, Selma, comes to that very same question herself after Homer gets sick from eating a jumbo sandwich that he’s been munching on for weeks. She gets a chance to see what it would be like to be a mother when she takes the Simpson children to Duff Gardens, which was like Busch Gardens or a beer themed version of Disney World, and well, as you could imagine, things do not go well.
I picked this episode since I think this would resonate with a lot of people in their 30s who don't have kids. I think this is a great episode to watch and it just might resonate.
“Deep Space Homer” (Season 5, Episode 15)
Space isn’t cool anymore in the ‘90s, so NASA decides to pull some guy off the street and send him into space to get people excited in space launches again. Well, it turns out that one such guy is Homer J. Simpson, and well, as you could expect, everything quickly goes wrong.
I’m picking this one since it seems super topical right now what with Richard Branson and Jeff Bezos taking trips into space recently. Now, I’m not calling either of them “guys off the street,” but this episode goes into the whole notion that maybe trips into space should be reserved for, I don’t know, actual astronauts?
“Homer Badman” (Season 6, Episode 9)
“Homer Badman” is the cancel culture episode before cancel culture was even a thing. Homer accidentally touches a college student’s rear end when he pulls a gummy off her butt (I’m serious) and the whole town rallies against him, thinking he’s a perv.
I’m picking this episode because it feels eerily similar to what sometimes happens in modern day times. Now, look, I’m not an apologist for anybody. If somebody says or does something wrong, then I think they should be called out for it and held accountable. But this episode also goes into the dark side of that, showing how lives can be completely destroyed even when there’s a misunderstanding. Being that this is The Simpsons though, it’s presented in the most hilarious way possible. “I just wish I had her sweet, sweet, sweetsweetsweet can.” Classic.
“22 Short Films About Springfield” (Season 7, Episode 21)
What I like to refer to as the Pulp Fiction episode, “22 Short Films About Springfield” is exactly as the title states: 22 short films about Springfield, and they all wrap around in the end, just like Pulp Fiction!
This episode gets picked mainly for one short film in particular, and that’s the famous “steamed hams” segment that you can find all over the internet in about a million different variations, like this one line-read by Jeff Goldblum. Because yes, this segment is that good. But the rest are pretty great, too, so watch it!
“Treehouse of Horror VII” (Season 8, Episode 1)
The annual Treehouse of Horror episodes are often the best episodes of each season, so I had to include at least one on this list. There are three segments for each Treehouse of Horror, and in my opinion “Treehouse of Horror VII” is the very best since every segment is a banger. The first segment is about Bart’s evil twin. The second is about a whole society being created from Lisa’s baby tooth, and the third, and best segment, is the aliens, Kang and Kodos, body swapping with then-Presidential candidates Bill Clinton and Bob Dole. And don’t blame me for who won that eventual match-up. “I voted for Kodos.” Which actually became the name of an early 2000s ska band. The more you know.
I’m picking this episode because it is the most consistently funny Treehouse of Horror of them all. In fact, if somebody asked me which Treehouse of Horror they should watch if they could only watch one, I would pick “Treehouse of Horror VII” by a mile. No doubt.
“Hungry, Hungry Homer” (Season 12, Episode 15)
Okay, now we’re getting into some dangerous territory here. A lot of “fans” of The Simpsons will tell you that the show stopped being funny after Season 10, but I highly disagree. Take for example Season 12’s “Hungry, Hungry Homer” in which Homer goes on a hunger strike to prevent his favorite baseball team, the Springfield Isotopes from moving to Breaking Bad stomping ground, Albuquerque, New Mexico.
“Hungry, Hungry Homer” is just a good story told well. It’s written by one of the most prolific Simpsons writers, John Swartzwelder, and was such a major episode, that Albuquerque literally made a minor league baseball team based off of this story. So, I guess Homer’s hunger strike was all for nothing. “Me so hungee.”
“Baby You Can’t Drive My Car” (Season 30, Episode 5)
Now we’re getting into critical damage territory! I jumped from Season 12 to Season 30, but for good reason! I honestly don’t know a single person who still watches The Simpsons since it hit a REALLY rough patch around Season 15 or so. But I don’t know if the show got new writers or what, but from Season 28 and onward, the show has gotten pretty damn good again. In this more recent episode, a new self-driving car company sets up shop in Springfield, and it seems like a really great place to work. But in a weird twist of corporate synergy, the car listens to people’s conversations and will refuse to drive people places if it feels it’s not good for the driver.
Now, The Simpsons has eerily been ahead of the curve by predicting a lot of things that would eventually come true, and the idea of a car listening in our conversations like Siri does actually sound like it could be right around the corner. This is like a comical version of a Black Mirror episode. But most importantly, it is comical. Just further proof that The Simpsons has still got it when it counts.
“Bart The Bad Guy” (Season 31, Episode 14)
And lastly, “Bart the Bad Guy” turns the mirror on all of us nerds who are so afraid of spoilers, then we might as well put our hands over our ears and shout, “La, la, la, la, la” whenever anything new comes out. In this episode, by happenstance, Bart sees the second part of a superhero movie, a la, The Avengers: Endgame, where he learns the ending. He goes around abusing this knowledge by making people give him things so that he doesn’t spoil it for them. Out of all of the episodes on this list, this one feels the most real to me. And how sad is that?
I think this is a great episode to conclude with since it is very-Marvel centric, so you will likely catch a lot of the references that the show is throwing at you. Again, The Simpsons has still got it.
And that’s the list. But what do you think? Have you seen a of these episodes before? If so, which one do you think is the best? Sound off in the poll below!
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Rich is a Jersey boy, through and through. He graduated from Rutgers University (Go, R.U.!), and thinks the Garden State is the best state in the country. That said, he’ll take Chicago Deep Dish pizza over a New York slice any day of the week. Don’t hate. When he’s not watching his two kids, he’s usually working on a novel, watching vintage movies, or reading some obscure book.