There are a lot of great animated TV shows these days for both kids and adults. My children, who are 8 and 7, enjoy programs like The Amazing World of Gumball, Pinky Malinky, and Teen Titans Go!
Whereas I, a grizzled, old man (who has no problem admitting that he loves the Trolls movies), dig more adult cartoons like Beavis and Butt-Head, Rick and Morty, and of course, Attack on Titan, which I once called the best under-the-radar show on television.
However, where both my children and my taste intersect is The Simpsons, which we all love. Now, while some of you might say, “Aren’t your kids too young to watch The Simpsons?” (Mind your business, by the way). My answer to that is no, because guess what! My kids are the same age that I was when I started watching The Simpsons. So, keeping the new Simpsons watcher in mind, here are the best The Simpsons episodes to watch if you’re new to the series. Ay, 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 in the entire series.
Homer meets his long-lost half-brother, Herb (voiced by Twins’ star, 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 most 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.
“When Flanders Failed” (Season 3, Episode 2)
There are a few characters who I actually think are just as funny as Homer and Bart, and one of those characters is Ned Flanders. Ned has a lot of great episodes, namely “Hurricane Neddy” from Season 8, but that episode only really works if you already know the character. If you don’t, then his wild outburst in that episode just doesn’t hit on the same level.
That’s why I’m picking “When Flanders Failed” for this list, since it’s a great introduction to the character, and one of the most wholesome episodes in the series. In this episode, Ned Flanders, who’s left-handed, opens up a left-handed store in the mall, and Homer being Homer, wishes that the store fails. Well, Homer ends up getting his wish, but in the conclusion, he sees the error of his ways, and it’s one of the few times that you really see that Homer, while he has his faults, is actually a great guy. It’s pretty heartwarming.
“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.
In the episode, Selma gets a chance to see what it would be like to be a mother when she takes the Simpson children to Duff Gardens, and well, as you could imagine, things do not go well.
I picked this episode since I think it would resonate with a lot of people in their 30s and 40s who don't have kids (and question if they even want them).
“Homer Badman” (Season 6, Episode 9)
“Homer Badman” is the cancel culture episode before cancel culture was really 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 am not an apologist for anybody (Especially when we hear horrific allegations about people like Vince McMahon).But this episode also goes into the dark side of that, showing how lives can be completely destroyed even when there’s been 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. Because yes, this segment is that good. But the rest are pretty great, too. So watch it!
“The Itchy & Scratchy & Poochie Show” (Season 8, Episode 14)
The Simpsons is well-known for its extensive list of characters, and many fans would have likely argued back in 1997 that we didn’t need anymore characters, especially not ones that could be considered “edgy.”
But, as mentioned on the Season 8 commentary for the DVD, the Fox executives disagreed, and requested that a new character be added to the show. Well, the writers apparently enjoyed poking fun at the idea, as they created one of the most annoying (and hilarious) characters ever in Poochie. The result is one of the funniest episodes in the entire series.
What makes this one such a good episode to show newcomers is because they’ll definitely see the satire in studio execs shoving new characters down our throats out of desperation to stay relevant. It also includes possibly my favorite Milhouse moment ever when he cries because the characters are taking too long to get to the fireworks factory. This one’s a keeper.
“Girly Edition” (Season 9, Episode 21)
My all-time favorite episode, “Girly Edition” has Bart and Lisa co-hosting a children’s news show. And while it might not be the episode that most people would recommend, for my money, some of the greatest moments in the entire series are in this mostly unassuming episode.
For one thing, it introduces one of the strangest The Simpsons’ characters of all time in the crazy cat lady (real name Eleanor Abernathy), but it also has one of the most nonsensical B-stories ever as Homer gets a monkey helper who you really need to pray for.
So, while a lot of people might point to milestone episodes like “Marge vs. the Monorail,” or “Last Exit to Springfield” when recommending The Simpsons, sometimes, the best episodes are the deep cuts, and “Girly Edition” is certainly one of those.
“Hungry, Hungry Homer” (Season 12, Episode 15)
Okay, now we’re getting into some dangerous territory here. A lot of Simpsons fans 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 really was for something.
“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! The Simpsons hit a rough patch around Season 15 or so and it lasted for several years. But honestly, from Season 28 and onward, the show got pretty good again.
In this 2018 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 them 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. Just further proof that The Simpsons has still got it when it counts.
“Panic On The Streets Of Springfield” (Season 32, Episode 19)
And lastly, I want to talk about one of my favorite more modern episodes, “Panic on the Streets of Springfield.” Lisa falls in love with the idea of a depressed, but heartfelt singer named Quilloughby, who is voiced by Benedict Cumberbatch, and goes through one of her phases.
The singer is, without a doubt, meant to be a parody of The Smiths’ Morrisey, and the writers had fun, as the English sometimes say, taking the piss with the character.
I would definitely show this episode to somebody who adores The Smiths since it’s such a loving send-up to the band, but also openly mocks Morrisey, who has been a controversial figure in his later years. For anybody who says The Simpsons stopped being funny years ago, I would definitely direct them to this episode to prove that that just isn’t true.
And that’s the list! For more news on all things The Simpsons-related, be sure to swing around here often!
