First things first: The Simpsons is the greatest show of all time. In fact, it is the greatest achievement in the history of humanity. The car? The polio vaccine? Yummy Mummy? All of these pale in comparison to The Simpsons. When a show is this good, and on the air for this long, it is guaranteed to generate some iconic characters. This beloved series is laden with some of the best character in all of television. In fact, it has tertiary characters more beloved than most main characters on other shows. As such, trying to come up with a ranking of its best characters is delightful and difficult in equal measures. A true fan could write a top 100 Simpsons characters list, and still feel like someone was given an unfair shake. Thus, my own attempt to pare it down to 20 almost feels like an act of heresy (like eating space-age, out-of-this-world moon waffles, instead of going to church). And yet, here we are. Here are my picks for the top 20 characters in the history of The Simpsons.
20. Hans Moleman
In a city full of characters with bad luck, Moleman (AKA Ralph Mellish) may have the worst of it. But, in truth, the joy of Moleman lies in the ill-fortune that the world brings upon him, and in his sad-sack voice. This ranking is for all of the times something happened like, say, Mr. Burns confusing him for the Lucky Charms Leprechaun and drilling into his head. “Oh no, my brains,” Moleman lamented. It’s true—nobody may be gay for Moleman, but he’s still fantastic.
19. Mayor Quimby
“Diamond” Joe Quimby may no longer be illiterate, but he is still a profoundly corrupt, philandering mayor who, somehow, always manages to keep his job, and thus his sash. Quimby is one of many incompetent politicians in the world of television, but it’s Quimby’s joie de vivre—which stems from his corruption and apathy—that makes him so much fun. Also, his Kennedy accent.
18. Hank Scorpio
Hank Scorpio only showed up once, in the episode “You Only Move Twice,” but he made such an impact that he absolutely belongs on this list. In part, it is in honor of the many one-off characters voiced by the brilliant Albert Brooks. Scorpio is, of course, a parody of a Bond villain, and, in his one small appearance, he got several classic lines that remain beloved to this day. Other one-off character considered for this list were Frank Grimes, or “Grimey,” as he liked to be called, and the kung fu hippie from Gangster City himself, Poochie.
17. Moe Szyslak
This choice required some mulling over. On the one hand, Moe is an odious character, and not always delightfully so. On the other hand, most of the time, arguably Springfield’s most depraved citizen (which is really saying something) usually mines plenty of humor from his sleaze. But the character has some depth, since, when he isn’t being a total creep, he’s being a suicidal misanthrope. For this reason, you can build whole episodes around Moe. They may not always be the funniest episodes, but you can’t do that with just anybody.
16. Lenny and Carl
Yes, Lenny Leonard and Carl Carlson are technically two characters. But they are, in the minds of many, forever intertwined. To think that, once upon a time, they were just a couple of guys that Homer worked with, lacking any real personality of their own. Now, they’ve done an entire episode about Carl’s Icelandic boyhood. Lenny gets more of the laughs, through his stupidity and propensity for eye injuries, but it’s his friendship (and perhaps something more) with Carl that really makes these two characters sing.
15. Ralph Wiggum
There are those of you who love Ralph Wiggum for one simple reason: he’s a non-sequitur machine. Of all the less-than-bright students at Springfield Elementary, Ralph is the dumbest. He makes a habit of saying strange, weird, and foolish things. A lot of people go wild for this sort of thing, and that’s fine. And he is quite funny, to be sure. But there’s a lack of depth to the character, and a superficiality to his lines, which keeps him from ranking too high on this list. That being said, we are talking about the 15th best character in the history of TV’s top show. Not too shabby for Ralph.
14. Sideshow Bob
It’s almost always a delight when Sideshow Bob stops by The Simpsons, even though he’s usually trying to kill somebody. What makes Bob so great, on top of Kelsey Grammer’s magnificent vocal performance, is that, while he is a violent maniac, he’s also an intellectual elitist, with a penchant for Gilbert and Sullivan musicals. He’s that rare TV villain that’s both fun to watch, and fun to laugh at—especially when he finds himself near a rake.
13. Lionel Hutz
When you needed a lawyer, and any lawyer will do, you call Lionel Hutz… or stop by his office in the mall. Maybe he hasn’t slept for days. Maybe he repeatedly ran over the son of the judge trying your case. But, if you end up losing, your pizza is free. Hutz also tried his hand at real estate, to very amusing results. Of course, Phil Hartman’s voiceover work is part of what made Hutz so great, but we’ve got more from Hartman coming up later.
12. Superintendent Chalmers
Bill Oakley, former Simpsons showrunner, often talks about his love of Chalmers, because he was the reasonable, sane man surrounded by idiots and weirdos. That has become less and less the case as the years have gone on; he remains angry, but less reasonable. But he’s still one of the best bit players in the show’s repertoire. Whenever he shows up to yell at Skinner, you know it’ll probably be a good time. Plus, if you steam a good ham, he’s happy to compliment you on it.
11. Kirk Van Houten
If you think Kirk’s son is a sad-sack, you should get a load of him. Kirk is, perhaps, the most pathetic man in all of Springfield. This would be sad, if he clearly wasn’t partially responsible, and whatever he’s not responsible for is existentially amusing in a cosmic sense. He used to be a superstar at the cracker factory. Then, things started falling apart, and a character who wasn’t especially compelling became one of the best on the show. Look no further than “Can I Borrow a Feeling?” for proof.
10. Bart Simpson
In the early days of the show, Bart was the breakout star. He put the mothballs in the beef stew, and he was this century’s Dennis the Menace. However, and this may be a bit of an unpopular opinion, he’s always felt a little overrated. Obviously, he’s a great character, and maybe, as a kid, you love the wacky antics of Bart. But as an adult, none of it works quite as well. However, over the years, he’s had so many great lines, and hilarious moments, and he’s been the focal point of so many episodes, that he’s definitely earned a top spot on this list. And those rare occasions when they’ve allowed Bart to have more “dramatic” storylines certainly helps, too.
9. Grampa Simpson
Grampa is sort of like an adult version of Ralph. He makes ludicrous statements and spouts nonsense, but he manages to be even funnier than Ralph, especially if you like the old-timey stuff. Essentially, every flashback shows that Abe was a miserable son-of-a-bitch as a younger man. But, as an old coot yelling at clouds and telling meandering stories that go nowhere, he’s almost always good for a memorable line or two.
8. Troy McClure
You might remember Troy McClure from… well, insert your favorite McClure project here. Why a faded actor was living in Springfield, we may never know, but it was certainly to our benefit that he was there. Whenever he showed up, and it was usually in an ad or an educational film, or some other bit of media within the show, we were treated to some of The Simpsons best moments. Troy didn’t show up as often as some of us would have liked, but when he did, he was always funny. For example, “A Fish Called Selma” was an excellent showcase for him as a character, just like the Planet of the Apes musical was an excellent showcase for the actor. And, of course, Hartman was fantastic. There was a tinge of phoniness in almost every line reading he gave, and it worked perfectly. In fact, let’s all queue up Christmas Ape Goes to Summer Camp in his honor.
7. Chief Wiggum
While Ralph just sort of shows up occasionally to spout silly nonsense, his father Chief Wiggum has a little more to do. He’s also a paradigm of both police incompetence and police corruption. He’s an authority figure with little authority, but he’s still willing to make the most of it. His badge reads, naturally, “Cash bribes only.” As a sort of older, more well-defined, and funnier version of Ralph, within the context of an authority figure, Wiggum has done plenty to earn his spot on this list.
6. Marge Simpson
Marge is in Homer’s shadow in many ways. Frankly, she’s probably in Bart’s shadow too. And there’s something unfair about this, because Marge is incredible. She represents a very different flavor of comedy, but she’s a tremendous member of the Simpsons in her own right. There is a subtle desperation and sadness on the fringes of her character that make her frequently sympathetic, and she’s probably the character most capable of carrying a more dramatic, emotionally-driven storyline. The funniest Marge moments come from the mundanity, and a certain defeatedness prevalent in much of what she says. She may not be as quotable as other characters, but even on The Simpsons quotability isn’t everything and Marge excels in every other area.
5. Principal Seymour Skinner
Oh, Skinner. When he’s not dealing with Bart’s antics, he’s dealing with his overbearing mother, or Superintendent Chalmers, or somebody else jumping down his throat. He always seems ready to break into a nervous sweat, and often does. There was also that one time when an elephant ate half his platoon back in Vietnam. The quintessential Skinner quote is probably this one: “If life has taught me one lesson repeatedly, it’s to know when I’m beaten.” It’s a brilliant line of dialogue, and perfectly synthesizes what makes Skinner such a great character. He’s pitiful, but in a wonderful way, and it all makes those moments where things work out for him so much better.
4. Milhouse Van Houten
Milhouse likes Vaseline on toast. Milhouse is everybody’s whipping boy. Milhouse is the best child character on The Simpsons. He’s got a bunch of great lines. How many people quote “Everything’s coming up Milhouse” with great frequency? His pain is our benefit, because, while Milhouse is incredibly put upon, he’s equally funny in these predicaments. Plus, he almost never loses his positive outlook. There’s always the chance things will turn around for him. That he will, truly, become the Thrillhouse he wants to be.
3. Krusty the Clown
Krusty is, as the chyron in “Behind the Laughter” informed us, an embittered comedy legend. Krusty is The Simpsons’ resident showbiz character. So, needless to say, he’s miserable, and angry and vain. He’s foolish with his money and spends most of his time doing drugs with a monkey. Kids love him, but nobody else really seems to respect him… and they probably shouldn’t. Krusty is the focal point of some classic episodes, and he’s incredibly important in one of the best episodes of the entire series, “Homie the Clown.” When Krusty is at his wit’s end, and Dan Castellaneta is wailing in anger, no character is funnier.
2. Mr. Burns
Basically, if you enjoy characters who say archaic things, you enjoy Mr. Burns. And who doesn’t like characters using 19th century insults and other words not heard in most contexts for decades? Sometimes he’s evil, and sometimes he’s just kind of a jerk, but it works well either way. The show’s writers have clearly enjoyed giving him cold, uncaring things to say, and making him a cutthroat businessman. And the fact that this villainous fellow is also incredibly old and enfeebled, makes all of his antics that much funnier. He’s quite out of touch, but that’s why we love him and it’s that cluelessness that makes him the second best character in Simpsons history.
1. Homer Simpson
Come on. Like it could be anybody else. Homer Simpson is the greatest character in the history of storytelling. No character has even been, or ever will be, funnier. There are literally hundreds of great quotes that have been uttered by the patriarch of the Simpson family. He’s done so many hilarious things, and seen so many misfortunes amusingly befall him. There will never be another like him, or anyone better on this great TV show.
Chris Morgan is not the author of THE book on Mystery Science Theater 3000, but he is the author of A book on Mystery Science Theater 3000. He’s also on Twitter.