I’m old. Do you want to know how old I am? So old, that I can say, “I was there, man” when The Simpsons debuted back in 1989 with “Simpsons Roasting on an Open Fire”. And since then, through good seasons and bad, I’ve stuck with the family for the past 31 years. In that period, I can tell you that Homer and Bart have definitely gotten the best storylines in the series, but this article isn’t about Homer or Bart (or any of The Simpsons family for that matter). No, this article is about all the OTHER denizens of Springfield, as the funniest Simpsons characters don’t necessarily have Simpson in their last name.
To wit, similar to how Baltimore could be considered the main character of The Wire, I think one could argue that the town of Springfield is really the main character of The Simpsons. Yes, early on, most stories centered around the Simpsons clan. But after 31 years on the air, the writers had to get creative, and we now have whole episodes devoted to Springfield’s other citizens.
But out of ALL those characters, who are the funniest? Well, you’re about to find out. Oh, and so I don’t step on any toes, I’m not ranking the characters. You’re just going to have to determine who’s the best on your own. I will also say which is the character’s best episode, in my humble opinion. Sound good? Okay! Then up and at ’em!
Mr. Burns (Best episode, “A Star Is Burns”, Season 6, Episode 18)
Conan O’ Brien’s favorite Simpsons character to write for is legendary for many reasons. First, he’s deliciously evil, but he also doesn’t realize why people don’t like him. So much so, that he will release the hounds on anybody if they disagree with him, or even if he’s just tired and wants to go to bed. Secondly, a lot of comedy also comes out of the fact that he’s so skinny. It’s not uncommon to find people just tossing him around like a beach ball and him commenting on how he’s not enjoying it.
But the best part about him might be his relationship with his obsequious employee, Smithers. They make a good duo. And even though a lot of the early laughs were centered around the fact that Smithers was in love with Mr. Burns, and he couldn’t read the signs, they have since gotten into a rhythm of Smithers being more of a caretaker than a butt kisser. Either way, you can’t go wrong with a Mr. Burns episode.
Ned Flanders (Best episode, “Hurricane Neddy”, Season 8, Episode 8)
The most sanctimonious citizen of Springfield is also one of the funniest. You can always count on Ned to say a prayer for Homer, even when Homer’s borrowing his lawn mower indefinitely. But the best moments are when Flanders drops the “diddly’s” and snaps, since you know he’s been holding those screams in forever. He kind of reminds me of Michael Douglas in the movie, Falling Down. Remember that flick? Michael Douglas was fine, but then just snapped one day. That’s Ned Flanders, and I live for those moments.
Ned is also funny when he’s not flipping out, though. All the characters really play off of him well, and it’s hilarious how he just takes Homer’s abuse and then turns around and prays to God to forgive him. Ned is like the super religious people in your life who try to push their faith on you, but unlike those people, Ned never wears out his welcome. God bless Ned Flanders.
Principal Skinner (Best episode, “The Road to Cincinnati”, Season 32, Episode 8)
Milquetoast mama’s boy, Seymour Skinner, is actually a Vietnam vet who saw some shit back in the day. He sometimes has flashbacks when Bart triggers him, but is often found sucking up to his mama when he wants to borrow her car. And the funny thing is, I used to laugh at Skinner when I was younger, but now that I’m a teacher, I find myself taking his side more than I do the kids. Screw Bart Simpson! That little scamp.
I just love how Skinner gets so nervous, though, especially around Superintendent Chalmers. His “Steamed Hams” bit has since become a huge internet meme, and for good reason. Principal Skinner is comic gold.
Moe Szyslak (Best episode, “Flaming Moe’s”, Season 3, Episode 10)
Springfield’s bartender has known The Simpsons for years, and yet, he still calls Marge “Midge”. A lot of people might take Moe for being aloof, and he is, but he also has a good heart when it counts. This makes his meanness all the funnier since you know it’s just because he’s been pushed to that point. Usually by Bart and his prank calls (“Amanda Hug and Kiss” is still my favorite).
Moe’s hilarious though, since he always has the most outlandish things to say when it comes to giving advice. A good bartender, a bad friend, and a pretty good bowler. That’s Moe Szyslak for you.
Patty and Selma (Best episode, “Homer vs. Patty and Selma”, Season 6, Episode 17)
I might be cheating a little by putting Patty and Selma here since they’re Marge’s sisters, but they’re not Simpsons (They’re Bouvier’s), and they’ll definitely let you know it. Lifelong smokers with raspy voices to prove it, Patty and Selma aren’t always together, but they’re always funnier when they are. Especially when they’re flat-out telling Marge to leave Homer with no chill. No chill at all.
They’re hilarious because they just don’t care if you find them annoying, and some of their best moments are when they’re laughing at people at the DMV. I feel like I’ve known people like Patty and Selma my entire life, but they’re not nearly as funny as these two sisters, even if they think they are.
Ralph Wiggum (Best episode, “New Kids on the Blecch”, Season 12, Episode 14)
Homer and Bart may get the best storylines, but Ralph gets the best lines. Son to the Police Chief, every line that comes out of Ralph’s mouth is going to be ridiculous to the point of hilarity. Sometimes, even stating the obvious is funny from Ralph, like when he says that his cat’s breath smells like cat food. Oh, yeah, Ralph? You don’t say?
But it’s always the reactions he gets from the other characters that makes him one of the funniest characters. He’ll flat out pee himself in front of everybody and they’ll just look at him like they didn’t even notice it. Or, that they’re so used to it that it doesn’t even phase them anymore. Oh, Ralph. Never change.
Mrs. Krabappel (Best episode, “Grade School Confidential”, Season 8, Episode 19)
Poor Mrs. Krabappel. I mean, yeah, it’s sad that she died, but it’s also sad that some parents mispronounced her name and kept calling her “Crab Apple.” Bart’s teacher is the better Ms. Hoover. Her sharp “Ha!” was almost a punchline in itself, and she was surprisingly sexy, like Blanche from The Golden Girls.
Her funniest moments though were usually with Bart. She both hated him, and also deeply cared for him, and as a teacher myself, I can understand that love/hate relationship with a student. Deeply.
Apu Nahasapeemapetilon (Best episode, “Much Apu About Nothing”, Season 7, Episode 23)
Now, yes, I know. Apu, an Indian character, used to be voiced by a white actor. But his accent was never what I found funny about his character. It was always more about the way he would overcharge the residents of Springfield because he was usually the only convenience store in town. And by God, he would benefit off of that.
Apu was made even funnier though with his wife, Manjula, had their eight children, and Apu went from a confident, and sometimes manic man, to a tired-all-the-time papa who was just trying to stay awake. It sucked when he cheated on his wife, but nobody said Apu was perfect.
Comic Book Guy (Best episode, “Married to the Blob”, Season 25, Episode 10)
Comic Book Guy is just The Simpsons writers having fun mocking their obsessive fans. I regularly put on his voice whenever I say something is the “worst ever”, but there’s also a lot of truth to his character and the way he’s so jaded by pretty much everything.
My favorite Comic Book Guy moments though are when he is entirely self-aware and actually a commentary on fandom in general, or corporations milking fandom. And when he once bemoaned the fact that he wasted his life getting obsessed over fictional characters, I felt that, man. Maybe a little too hard, even.
Fat Tony (Best episode, “The Mook, The Chef, The Wife and Her Homer”, Season 18, Episode 1)
Voiced by Criminal Minds actor, Joe Mantegna, Fat Tony is pretty much every mafia type rolled into one, and I love it. Kind of like how Rainier Wolfcastle and Drederick Tatum are ways for The Simpsons writers to riff on action stars like Arnold Schwarzenegger and the boxer, Mike Tyson, respectively, Fat Tony is a stand-in for Goodfellas and The Godfather references. And hey, The Sopranos, too. Why not?
Mantegna’s delivery, though is one of the reasons why he’s such a funny character. I especially love when he talks about how his wife keeps asking him “Where is da money?” An over-the-top stereotype, yes, but a funny one.
Reverend Lovejoy (Best episode, “Bart’s Girlfriend”, Season 6, Episode 7)
Reverend Lovejoy, with his toy trains and his fake piety, is great mostly because he’s not even the most religious person in town. With his nasally, dry delivery, he’s also hilarious since you really have no idea what he’s going to say next, or how unholy it will actually be.
Because unlike somebody like Krusty, who is intentionally over-the-top, Lovejoy’s humor is always deadpan, and the kind of humor that is often funny when you actually sit on it for a little while. A vastly underappreciated character when it comes to the series.
Agnes Skinner (Best episode, “22 Short Films About Springfield”, Season 7, Episode 21)
And lastly, I need to talk about Skinner’s mother, Agnes. I was going to pick The Cat Lady, but she’s too one note of a character. Agnes’s whole bit of being mean to her son, is also kind of one note, but every condescending line that comes out of her mouth is comic gold.
I also love that she is almost never happy, and the only time she is happy, is when she’s wondering why her son can’t be more like somebody else. Sure, her character doesn’t work without Skinner, but neither does Lenny without Carl, or Smithers without Mr. Burns. And as an enhancement to another character, I think she’s definitely the best.
And those are 12 of the funniest The Simpsons characters who aren’t part of the Simpsons clan. But what do you think? Is there anybody you think I missed? For more articles on The Simpsons or other shows in the 2021 Fall TV schedule, make sure to swing by here often!
Lover of Avatar (The Last Airbender, not the blue people), video games, and anything 90s, he will talk your ear off about Godzilla, so don’t get him started.