The 100 Greatest ‘Simpsons’ Characters

100 Jebediah Springfield

What would a list of the greatest Sprinfieldians be without the town’s namesake? Sure, he was a murderous pirate who once threatened George Washington with an ax, but he also inspired his followers with the legendary quote, “A noble spirit embiggens the smallest man.” He’s Springfield’s own Christopher Columbus, part myth, part horrible monster, so precisely the kind of guy you’d want to steal the head of. — Brian VanHooker, Senior Features Writer 

99 Bumblebee Man

The rise of Simpsons-mania in the 1990s coincided with the increased visibility of Spanish-speaking cable networks. Like many of us during the decade, the show’s writers frequently channel-surfed and found themselves entranced by a Spanish channel with an “always on” Mexican comedic performer named Chespirito and his grasshopper-costumed superhero character El Chapulín Colorado. Inspired by this ubiquity, they created Bumblebee Man, a man in a bumblebee costume who has mastered the delicate art of combining physical comedy with beginner-level Spanish. 

The show has gone back and forth regarding his true nationality — including Belgian, Norwegian and British — but Bumblebee Man speaks to us all via the universal comedic language of oversized props causing physical pain. — Chaz Kangas, on-air radio personality for The Current 89.3 (KCMP), freelance writer for The L.A. Times and BringMeTheNews

98 Poochie

“Funny Dog to Make Life Worthwhile” reads the headline of The Springfield Shopper in anticipation of the debut of Poochie — the totally in-your-face character created to “update” Itchy & Scratchy. The perfect amalgamation of corporate meddling to create something trying way too hard to appeal to youngsters, Poochie was “half Joe Camel and a third Fonzarelli.” But, sadly, he wasn’t the type of outrageous dude the public wanted and was firmly rejected. One of the show’s most memorable one-offs — with a meta-commentary on both corporate over-reach and toxic fandoms that is still very potent today — real-life Simpsons fans were happy(?) to see Poochie return as one of the villains in the “Grand Theft Scratchy” segment of 2007’s The Simpsons Game. — Chaz Kangas

97 Rich Texan

His name says it all. The trigger-happy, obsessive-compulsive good ol’ boy is Springfield’s living embodiment of every Lone Star Republican stereotype. He drills for oil in Springfield and once tried to cut down the town’s oldest redwood tree. His license plate reads “NO SHAME,” which sums him up pretty perfectly. — Brian VanHooker

96 Squeaky-Voiced Teen

Relatable to all of us at some, hopefully short-lived, point in our lives, the Squeaky-Voiced Teen has been seen trying to get by at every minimum-wage job in Springfield. While he’s usually just trying to stay out of trouble with his ever-changing boss, there is a bit more to this character than his prolific employment history. For one, did you know that he has a name? It’s Jeremy Freedman. He’s also the son of Lunchlady Doris. Okay, that’s it. There’s nothing else to know about this guy. — Chaz Kangas

95 Blinky

Blinky is basically The Simpsons’ version of a Pokémon. Admittedly, the three-eyed fish has faded in popularity over the past three decades, but Blinky was once a prominent symbol of The Simpsons and was featured in early Simpsons toys and video games. He was created by Mr. Burns’ careless disposal of radioactive chemicals, and his mutated face still tickles the nostalgia bone of Simpsons fans who have been around since the beginning. — Brian VanHooker

94 Joey Jo-Jo Junior Shabadoo

Joey Jo-Jo Junior Shabadoo was a name Homer thought he was making up when asking Moe for advice while not wanting to reveal that it was his own problem. Once the name left Homer’s lips, a man at the end of the bar lifted his head in acknowledgment, only to be met with Moe’s cold dismissal, “That’s the worst name I ever heard.” The very real Joey Jo-Jo Junior Shabadoo then ran out of the bar crying. His distinct character design made an unnamed appearance once before and once again after this scene, but nothing beats this incredible take on the long-lasting “struggling to make up a name” gag. — Chaz Kangas

93 Sherri and Terri

There’s not much to these girls — to this day, we don’t know which is which, and neither do the Simpsons — but Sherri and Terri are mainstays of the show as Bart’s classmates. The first of two sets of twins on this list, they’re literally two characters-in-one, often simultaneously speaking and finishing each other’s sentences. Initially, they were know-it-alls who looked down on Bart’s behavior, but eventually, they became more generic and behaved like normal children. We didn’t even know their last names until a brief sight gag in Season 25. (It’s Mackleberry.) — Neil Arsenty, On This Day in Simpsons History on Twitter and freelance writer for Cracked

92 Dewey Largo

Who? Lisa’s surly music teacher isn’t all that remarkable, both to Simpsons fans and within the town of Springfield, yet he’s had a few memorable moments (like when he filled in for Groundskeeper Willie). He’s also featured prominently in the show’s opening credits, so how about showing him some respect? Or don’t. That’s fine too. — Brian VanHooker

91 ‘Just Stamp the Ticket Man’

He isn’t in the show all that much — and never even received a proper name — but the so-called “Just Stamp the Ticket Man” was hugely important in fleshing out the world of the show in its early seasons. We saw him aggressively grifting Flanders for parking validation at the Leftorium, coolly insulting Marge’s wishbone necklaces and even punching a friendly busker on the street because of the heat. “Just Stamp the Ticket Man,” it could be argued, was a human embodiment of the town as a whole, representing Springfield’s core selfishness and casual disregard for basic human decency. — JM McNab, contributing writer

90 Captain McCallister

Like Bumblebee Man and Rich Texan, Captain Horatio McCallister is another one-note Springfield character who appears for a quick joke before sailing off into the sunset, only to return when the next joke calls for his seafaring sensibilities. While The Simpsons has successfully given occasional depth to some of these characters — like Duffman — Captain McCallister remains unsullied by pathos or character development, and that’s exactly what we love about him. — Brian VanHooker

89 Cletus Spuckler

Springfield’s favorite redneck has an appetite for possums, a loving wife/sister and more children than he has teeth. He’s one happy slack-jawed yokel, and, in addition to his fair share of memorable quotes and moments, his entry in “22 Short Films About Springfield” was a highlight in an episode jam-packed with classic moments. — Brian VanHooker

88 Artie Ziff

Artie Ziff deserves a place on this list, not just because he’s the longest-running Jon Lovitz-voiced character, but because he so clearly crystalized why Homer and Marge’s relationship works. First introduced in the flashback episode “The Way We Was,” Artie is everything Homer isn’t — smart, successful, and respected. But he’s also a toxic creep. When Marge clues into Artie’s awfulness, she’s drawn to Homer’s innocent sweetness. Artie, on the other hand, never gets over Marge, so much so that he eventually builds a basement full of Terminator-like Marge-bots. — JM McNab

87 Mr. Sparkle

He is disrespectful to dirt! Can you see that he is serious!? As it turns out, in the universe of The Simpsons, the Japanese equivalent of Mr. Clean is a dead ringer for Homer. Mr. Sparkle loves to scrub dishes and does not tolerate loose, loafing women. Mr. Sparkle is one of those Simpsons gags that barely makes any sense at all, yet he’s as beloved as any dictatorial detergent mascot could be. — Brian VanHooker

86 Hugh Jass

“Hugh Jass? Will someone check the men’s room for a Hugh Jass?” Moe shouted from behind the bar after getting a phone call. Of course, this was one of Bart Simpson’s many crank calls, but in the episode “Flaming Moe’s,” it backfires as a man named Hugh Jass was actually in the bar. What makes the scene — and, by extension, this character — truly hilarious isn’t that there’s a guy with this ridiculous name. It’s the way Hugh reacts to Bart that makes him great. After Bart comes clean about the prank over the phone, Hugh simply says, “Better luck next time,” and hangs up, remarking to himself, “What a nice young man.” If only the rest of Springfield were as charmed by Bart’s antics. — Brian VanHooker

85 Spider Pig

Technically his name is Plopper, but you probably best remember him as Spider-Pig, as in “Spider-Pig, Spider-Pig / Does whatever a Spider-Pig does / Can he swing from a web? / No, he can’t, he’s a pig, / Look out, he is a Spider-Pig!” The undisputed highlight and lasting legacy of 2007’s The Simpsons Movie, Plopper/Spider-Pig, was also the first major Simpsons meme of the Myspace era. — Chaz Kangas

84 Lindsey Naegle

Businesswoman/sexual predator Lindsey Naegle is one of the later additions to the show that makes this list, surprisingly not making her first appearance until Season Eight’s “The Itchy & Scratchy & Poochie Show.” Interestingly, Naegle went unnamed in her first three appearances until Season 10’s “They Saved Lisa’s Brain.” Although she doesn’t have that many memorable quotes, her appearances are always funny, thanks mostly to Tress MacNeille’s razor-sharp delivery. — Neil Arsenty

83 Very Tall Man

Like Hugh Jass and Joey Jo-Jo Junior Shabadoo, the Very Tall Man — named “Ian” — is a one-joke character in a profoundly funny gag. The only reason he outranks those other, equally funny dudes is that the Very Tall Man has also caught on as an internet meme. — Brian VanHooker

82 Crazy Cat Lady

Crazy Cat Lady is another character that we can mostly thank actress Tress MacNeille for making memorable since her regular appearances mainly involve her just yelling and throwing cats at people. — Neil Arsenty

81 Arnie Pye

Arnie Pye makes this list for no other reason than the following observation: His name is Arnie Pye and he hosts a helicopter-based news segment usually called “Arnie in the Sky.” His show should clearly be called “Pye in the Sky,” but it isn’t. We may not know much else about the oft-disgruntled reporter, but this hilarious, subtle joke earns him a place on this list. — Warren Evans, Bart of Darkness on Instagram and Twitter, and host of Simpsons Is Greater Than… podcast

80 Baby Gerald

As Lisa Simpson once said, “Everybody needs a nemesis. Sherlock Holmes had his Dr. Moriarty. Mountain Dew has its Mello Yello. Even Maggie has that baby with one eyebrow.” That baby is Gerald Samson. Born on the same day as Maggie at Springfield General Hospital, their rivalry goes back to Maggie getting the hospital’s last remaining diaper, forcing Samson to don a wrapped copy of The Springfield Shopper, causing him to develop a rash that he’s said to still have to this day. — Chaz Kangas

79 Marvin Monroe

Marvin Monroe was the deluded fool who thought he could fix the Simpsons with therapy in the very memorable early episode “There’s No Disgrace Like Home.” Throughout the show, we’ve seen Marvin come and go (even from the cold clutches of death), often acting as an expert in one field or another but never quite as prominently as other characters. Regardless, his early introduction and very early design style make him near impossible to forget. — Warren Evans

78 Disco Stu

What started as a one-off joke about Homer running out of the room when “Disco Stud” was being bedazzled on the back of his jacket, the 1990s obsession with 1970s nostalgia resulted in Disco Stu being the long-lasting stand-in for people who can’t give up the past. Continuing to make appearances to this day, we’re happy Disco Stu is still “Staying Alive.” — Chaz Kangas

77 Jessica Lovejoy

We hadn’t seen her before and really haven’t seen her since, but Jessica Lovejoy, the seemingly-good-but-actually-rebellious daughter of Reverend Lovejoy, made quite the impact in “Bart’s Girlfriend.” Meryl Streep portrayed her good, bad and ugly sides so believably that we completely understand how Jessica could get away with anything. However, her lack of appearances since makes us believe the Lovejoys may have her permanently locked away. — Neil Arsenty

76 Luann Van Houten

While not the most widely celebrated of the Van Houten clan, Luann provides a unique comic force in her own right, as evidenced by, say, the time she casually set fire to Kirk’s possessions. Like Kirk and Milhouse, Luann’s blandness is often played for laughs, but she’s clearly got much more going on beneath the surface. I mean, her maiden name is “Mussolini” for crying out loud. — JM McNab

75 Rabbi Krustofsky

Voiced by comedy legend Jackie Mason in an Emmy-winning performance, Rabbi Hyman Krustofsky was a highly-respected Rabbi in Springfield’s Lower East Side whose falling out and reuniting with his son Krusty remains among the show’s most touching moments. — Chaz Kangas 

74 Roger Meyers Jr.

Roger Meyers Jr. is the son of Roger Meyers Sr., the founder of Itchy & Scratchy Studios. As the heir to his dad’s cartoon empire, Meyers is a less-scathing portrayal of a studio exec than one might expect from the show; while he was initially positioned as an antagonist for Marge’s anti-violent cartoon protests, the cigar-chomping, gravel-voiced Meyers seems to genuinely care about the quality of his cartoons, even if he’s kind of a jerk about it. — JM McNab

73 Laura Powers

Few people contribute to Bart’s growth as a character as much as Laura. In the Season Four episode “New Kid on the Block,” Bart’s babysitter and teenage crush challenged him in a new way, shaking the foundation of his priorities. Bart falls for her but also experiences real heartache for the first time. By the end of the episode, Bart seems like less of a brat. In the never-aging world of The Simpsons, Bart and Laura never could last, but it’s nice to think that part of this experience still sticks with Bart. — Warren Evans

72 Lunchlady Doris

One of the joys of growing up as a Simpsons fan are the moments relating to school satire. Whether you’re a kid in the middle of living it or an adult remembering it, chances are that Springfield Elementary conjures up some sort of pointed memory — especially Lunchlady Doris. Voiced by the late, beloved Doris Grau — who The Critic fans may recognize as the voice behind makeup lady Doris — Lunchlady Doris’ monotone delivery made you really believe that she’d grind up gym mats into school lunch meat. Despite Grau’s real-life death in 1995, Lunchlady Doris was kept on the show as a silent background character until her voice was recast, and she was renamed Lunchlady Dora in 2006. — Chaz Kangas

71 Judge Roy Snyder

The serious-minded Judge Roy Snyder is a sleeper entry. He’s probably nobody’s favorite character and is often outshined by much funnier court-based characters like Lionel Hutz, but Judge Snyder does a lot of heavy lifting in the show as Springfield’s most prominent judge. Considering how often the Simpson family ends up in legal trouble, Snyder has always been a funny, reliable straight man. — Brian VanHooker

70 Sideshow Mel

He had some big shoes to fill when replacing Sideshow Bob, but the likewise sophisticated Sideshow Mel holds his own pretty well. He only had minor appearances before truly shining in “Who Shot Mr. Burns? Part Two” when he took a Sherlock Holmes-type role in trying to solve the mystery, getting Smithers freed in the process. Trivia tidbit: The bone in his hair is apparently stuck in there by bubble gum. — Neil Arsenty

69 Üter Zörker

This rotund little German boy just wants to enjoy his confectionery treats in peace, yet Springfield’s foreign-exchange student is often subject to bullying, sometimes even by Principal Skinner. He’s a pitiable character; fortunately, Groundskeeper Willie has got his back as a fellow immigrant. — Brian VanHooker

68 Guy Incognito

Yes, we only saw this impossibly-named character in one episode from Season Six; still, somewhere in Springfield, there exists a person who looks exactly like Homer if Homer were dressed in a horrible, unconvincing costume. If only that dog with a puffy tail hadn’t come along, we might know more about this mysterious man. — Warren Evans

67 Shauna Chalmers

Shauna is a character who some viewers may be less familiar with. Maybe they stopped watching the show a long time ago or perhaps didn’t really notice her. Either way, Shauna is the daughter of Superintendent Chalmers, and she brings something unique to the show. Since her debut in Season 20, she has dated the Squeaky-Voiced Teen, Jimbo and even Bart. But unlike so many other characters, she actually sticks around. We see her be a mentor for Lisa in “Girls Just Shauna Have Fun.” She also sells weed to Mr. Largo, is a perfectly sarcastic employee at any number of jobs and draws one hell of a Sharpie tattoo. — Warren Evans

66 Hans Moleman

The Simpsons could totally exist without Hans Moleman, but it would be a far worse show, dammit. Yes, he’s a background character, but Hans’ diminutive, bespectacled, distinctly peanut-like exterior, combined with his over-the-top sad-sack nature, make him one of Springfield’s most idiosyncratic residents. Hans Moleman is also, arguably, the show’s most mystifying character, considering that he has seemingly died near-countless painful deaths ranging from immolation to capital punishment to crashing with a truck carrying Edgar Allen Poe’s childhood home. — JM McNab 

65 Kearney

Sure, perhaps Kearney is not the most remarkable of Springfield Elementary’s resident bullies, but there is more to him than meets the eye. For starters, he’s divorced and has not one, but two children — at least one of whom sleeps “in a drawer.” Both dim-witted and hulking, Kearney actually feels like a real threat to the nerds of Springfield, much more so than Dolph or Jimbo (he’s particularly dangerous when wielding a Newton tablet). — JM McNab 

64 Mr. Bergstrom

Mr. Bergstrom is a traveling substitute teacher full of passion and the quest for real experience. The particularly touching episode “Lisa’s Substitute” is a favorite among fans because of its strong writing and unforgettable performance of Mr. Bergstrom by Dustin Hoffman. He’s really only featured in that one episode, but he certainly made an ever-lasting impression in it. — Warren Evans

63 Jimbo Jones

It’s easy to dismiss Jimbo as one of Nelson Muntz’s background bullies, yet there’s more to him than, say, Dolph (who didn’t even make this list). Jimbo may be a thief and a jerk, but he’s occasionally shown kindness to Bart and once even hesitated to beat up Martin (he still did, though). He’s legitimately “the worst kid in school,” but he’s not as evil as, say, a sentient Krusty doll. — Brian VanHooker 

62 Rod and Todd Flanders

It was a difficult decision to pair the two Flanders kids together as one, Todd, is slightly better (having successfully become an internet meme when he quipped to his mother that he didn’t want “any damn vegetables”). However, these two are usually inseparable, whether they’re celebrating “Imagination Christmas” or having a sugar rush from Pixy Stix. They’re rarely anyone’s favorite characters, but indeedly-doo have many great moments together. — Neil Arsenty

61 Maude Flanders

The devout wife of the pious Ned Flanders, Maude Flanders’ untimely death was a major turning point for the show and, for many, the point of no return. While the show had dealt with death before (Bleeding Gums Murphy) and had alleged shark-jumping moments previously, Maude was a longtime character whose demise was directly caused by Springfieldian negligence and/or Homer’s selfish stupidity. 

But enough about her death, her life and afterlife have both been memorable parts of the show. Her salacious suburban gossip and subtle dry lines — “Neddy doesn’t believe in insurance. He considers it a form of gambling” — has led to some of the more rewarding moments of fans’ re-watches. Meanwhile, her presence as a spirit has additionally been one of the show’s bittersweet bits of optimism. — Chaz Kangas

60 Dr. Hibbert

The rare Springfield combination of intelligence and competence, Dr. Hibbert’s long-standing presence on the show has mostly been as a straight man for the absurdity around him. A family man, trusted medical practitioner and Rocky Horror Picture Show enthusiast, his trademark chuckle at inappropriate moments makes the perfect tonal segue whether delivering terminally upsetting news or giving greatly welcome relief. — Chaz Kangas

59 Agnes Skinner

Agnes has some of the funniest lines in the entire show, delivered flawlessly by Tress MacNeille. The dynamic between Agnes and her son, Seymour, perfectly explains his personality (he once referred to her as his “beloved smother”). Whether it’s fighting over the bath pillow or charging Seymour for the food he ate as a kid, situations surrounding her are always hilarious. — Warren Evans

58 Drederick Tatum

If you ever saw Springfield’s top athlete Drederick Tatum on-screen, you knew some shit was about to go down. A parody of America’s obsession with boxers and combat celebrities that defined the latter half of the 20th century, Tatum was an Olympic gold medalist said to have won his first world championship at a pay-per-view titled “The Bout to Knock the Other Guy Out!” With a voice and violent past that birthed all 1990s Mike Tyson parodies, Drederick’s continued presence in Springfield has allowed him to blossom into his own character. — Chaz Kangas

57 Jasper Beardsley

This old man is a meme machine. Jasper, the long-bearded resident of Springfield Retirement Castle, has enjoyed more than his fair share of memorable moments on The Simpsons, like when he got stuck in Apu’s freezer and his haunting rendition of “Theme from a Summer Place.” He’s usually mild-mannered but has a hidden harsher side as well, like, if he catches you talking out of turn, well, that’s a paddlin’. — Brian VanHooker

56 Snake Jailbird

Springfield’s most wanted man is constantly preying on Springfield’s greedy and/or stupid. Snake is continuously in and out of incarceration for his many, many crimes in town, though he was never properly punished for his worst transgression of all: subjecting the fans to a clip show. — Brian VanHooker

55 Officers Lou and Eddie

Another combo entry on this list, Officers Lou and Eddie (they don’t have last names), are hardly model police officers, but they somehow manage to be just a bit smarter and better at their jobs than their boss, Chief Wiggum. Their preeminent appearance is likely in “Separate Vocations,” where they take Bart on a ride-along and give him insight into Springfield’s criminal underbelly. — Neil Arsenty

54 Lurleen Lumpkin

Some of the show’s highlight-reel episodes are the ones in which Homer and Marge’s marriage is genuinely tested. In Season Three’s “Colonel Homer,” temptation comes in the form of Lurleen Lumpkin, a sexy, honey-voiced country singer that Homer takes under his wing. On paper, this sounds like a pretty goofy plotline, but in execution, we get a story that mixes heart-rending relationship drama with jokes about Hee Haw. 

Imbuing Lurleen with soul and talent was the voice of the great Beverly D’Angelo, who previously showed off her country music chops playing Patsy Cline in Coal Miner’s Daughter. It’s no wonder Lurleen was brought back for a follow-up episode in Season 19 after years of minor cameo appearances. — JM McNab

53 Mindy Simmons

Homer’s greatest temptation, who could ever forget the most palpable animated sexual tension to hit television screens? — Chaz Kangas

52 Jacques

Guest star Albert Brooks’ second-best character on The Simpsons, Jacques was initially intended to be Swedish (and named Bjorn), but Brooks suggested making him French. As with his other appearances, Brooks was allowed to improvise much of his dialogue, many moments of which made it to the final cut (“Four onion rings!”). This is also the only character that Brooks has reprised on the show: Once briefly in Season 16’s “The Heartbroke Kid” and just recently in Season 34’s “Pin Gal.” — Neil Arsenty

51 Gil Gunderson

Gil is somehow so sad and pathetic that his chronic bad luck has made him downright endearing. In the criminally-underrated Christmas episode “Kill Gil, Volumes I & II,” Gil loses his job because he sells a toy to Lisa that was being held for the boss’ daughter and is forced to live with the Simpsons for a while. Classic Gil. — Warren Evans

50 Lyle Lanley

One of three characters on this list voiced by the late, great Phil Hartman, the melodic, monorail-hocking huckster is front and center in one of the most beloved episodes in the show’s history: the Conan O’Brien-penned “Marge vs. the Monorail,” which mirrored The Music Man. While Hartman’s other characters, Lionel Hutz and Troy McClure, have cumulative greatness, Lyle Lanley only ever needed a single episode to make him memorable. — Brian VanHooker

49 Hugo Simpson

Some of you probably don’t think Hugo deserves to be here because he isn’t “canon,” but few concepts presented by “Treehouse of Horror” episodes stick with people quite as much as Bart’s formerly-conjoined twin Hugo, who has spent his existence in the Simpsons attic eating fish heads. The reveal that he’s actually the “good” twin is especially hilarious, even more so after the release of Jordan Peele’s Us. — Warren Evans

48 John

In the Season Eight episode “Homer’s Phobia,” Homer distances himself from John, a gay character played by John Waters, due to fears of his impact on Bart. However, John’s story represents a genuine shift in Homer, as he eventually learns to accept John and becomes more accepting of Bart. While a valuable commentary on homophobia, the John character is also used to perfection in pointing out the many silly reasons that some people are homophobic. — Warren Evans

47 Professor Frink

A Jerry Lewis parody who’s essentially become several generations of viewers’ introduction to Jerry Lewis-esqe humor, Professor Frink is another fabled Springfield denizen intended for a one-off joke who’s become a very welcome running character. A mid-level mad scientist with seemingly good intentions that overcomplicate into disaster, there’s a special love for Springfield’s off-brand nutty professor among gamers as he’s a major part of The Simpsons Hit & Run, which is universally considered the greatest Simpsons video game ever made. His nasal voice is cited by Hank Azaria as his favorite to perform and one he’ll start doing on his own, even when not recording, to pick himself out of a bad mood. “GLAYVIN!” — Chaz Kangas

46 Duffman

Duffman, or Barry, as some of us know him, has only continued to develop as the show continues. Once just a symbol for 1990s beer commercials, Duffman has gone on to show actual depth within The Simpsons universe. In the Season 34 episode “From Beer to Paternity,” we learn that he has a teenage daughter, seeing an entirely new side of him. He also makes for a killer Halloween costume, with his catchphrase “Oh yeah!” making him all the more memorable. — Warren Evans

45 Reverend Lovejoy

Reverend Lovejoy was a one-time Christian idealist who eventually gave up caring after years of being pestered by the overly virtuous Flanders. The Simpsons could have been a lot harsher in its depiction of organized religion, but Springfield’s Presbylutheranism minister is still a fairly sly condemnation of the church — tedious, judgemental, opposed to “rock and/or roll.” Reverend Lovejoy is a good person, but he’s also the perfect buzzkill (with the exception of that one time when he fought off a horde of bloodthirsty baboons). — JM McNab

44 Dr. Nick

If a conman is transparent about being a conman, does that make him honest? So exists the paradox of the patron saint of second opinions, Dr. Nick Riviera. A send-up of charismatic-but-dubious media darling doctors that’s only become more biting with time, Dr. Nick is a graduate of “Hollywood Upstairs Medical College” with degrees from “Mayo Clinic Correspondence School,” “Club Med School” and “Female Body Inspector.” While seemingly killed in The Simpsons Movie, he continues to appear on the show, further proving you can’t keep a bad doctor down. — Chaz Kangas

43 Martin Prince

Martin was a pretty unlikeable nerd when debuting in “Bart the Genius.” Still, he’s managed to get a little more interesting as the show has gone on, especially as his wussiness has become more laughable. His disdain for his parents at “image enhancement camp” and his summer popularity bump from having a superior pool are just two of many highlights. When Martin’s longtime voice performer Russi Taylor died in 2019, the producers made the rare decision to continue with the character, now played by veteran voice artist Grey DeLisle. Thankfully, she hasn’t missed a beat and has even helped deliver a new facet to the character. — Neil Arsenty

42 Kent Brockman

The longtime anchor of Eye on Springfield, Kent Brockman provides the perfect amalgamation of every local news trope. Kent covers all bases, from the vocal timbre that can go from deathly serious to pure whimsy in a split-second, to the hard-hitting blunt interview style for local topics that may not warrant it, to jumping to rash conclusions in a professional voice for that perfect level of attention-grabbing shock. There’s a good reason that he’s any loyal Simpsons viewer’s choice to be the one to welcome “our new insect overlords.” — Chaz Kangas

41 Bleeding Gums Murphy

“You ever been to the dentist? Not me. I suppose I should go to one, but I got enough pain in my life as it is.” So begins the first of many unforgettable tidbits about one of television’s favorite fictional jazzmen, Bleeding Gums Murphy. Arguably the standout non-family character of the show’s first season, his subsequent appearances would function as a great send-up of burnt-out musicians (blowing his fortune on Fabergé eggs) and artistic indulgence (his 26-minute long rendition of the national anthem). Still, his mentorship of Lisa helped her grow as a character exponentially. The show’s first major death, his presence is still seen and felt in the series. — Chaz Kangas

40 Otto Mann

You could argue that Otto is the best glimpse into Bart’s future, but he’s much more than that. Otto might smoke a lot of weed, shred guitar solos and hate false advertising, but he drives that school bus as if it were his lifelong dream. — Warren Evans

39 Herb Powell

In the days before The Simpsons was a revolving door for big-name guest stars, the one-and-only Danny DeVito guest starred in Season Two as Homer’s long-lost brother, Herb Powell. At times, Herb is a typically grouchy DeVito-type character but is also shown to have a soft side for Homer’s family. That is until Homer ruined his life by inventing the worst car Herb’s auto manufacturer ever made. To date, he’s only made two appearances (and one brief cameo) on The Simpsons and is exactly the kind of classic character we need more of. — Brian VanHooker

38 Rainier Wolfcastle

The 1990s had no shortage of Arnold Schwarzenegger parodies, but none have had the lasting power of Rainier Wolfcastle and his signature role of “McBain.” A send-up of Reagan-era muscle-bound action stars, Wolfcastle never met an on-screen explosion or revenge mission he didn’t like. Even his forays into other genres, most notably the massive meme-spawning McBain: Let’s Get Silly, echoed Arnold and others’ real-life attempts at crossing over. Wolfcastle also amassed political influence in Springfield, something the “Governator” managed to do as well. — Chaz Kangas

37 Mayor Quimby

“Diamond” Joe Quimby may not have been American television’s first scathing portrayal of a modern self-serving politician, but he’s probably the funniest. The Kennedy-esque voice makes him both believably inspirational as well as understandably slick with his law-making lothario ways. As corrupt as they come, it’s shocking yet understandable that he continues to get re-elected. A media darling when he wants to be, Quimby was said to have immediately won the public back after confessing to using tax dollars to fund the murder of his enemy by utilizing his campaign slogan “I’m a bad wittle boy.” — Chaz Kangas

36 Radioactive Man

Radioactive Man is not only Bart’s favorite comic book character, but he also acts as a vehicle to look beyond Springfield. There is something fans love about content-within-the-content, and this is why Radioactive Man was turned into a real-life comic book when Bongo Comics started back in 1993. The issue numbers would always jump around, allowing you to see the many different eras of the character. Honestly, this comic book series pushes Radioactive Man higher on the list than he would be if just counting his sometimes-underwhelming presence on the show itself. — Warren Evans

35 Kang and Kodos

A staple of basically every “Treehouse of Horror” for the last 32 years, Kang and Kodos have become a symbol of Halloween for all of us. Their debut appearance, when Lisa and the audience are led to believe they want to eat the Simpsons clan, is one of the funniest Treehouse segments and ranks among the strongest jokes the show would ever make. You could argue that they would deserve to be on this list even if that was the first and last time we saw them, but thankfully, they’ve been around ever since. Bless Rigel 7 for their existence. — Warren Evans

34 Mona Simpson

Homer’s estranged mother, Mona (voiced by Glenn Close), packed an emotional wallop when she first appeared back in Season Seven. Seriously, has the show given us a more touching image than that of Homer contemplating life while gazing up at the heavens at the end of “Mother Simpson”? 

The revelation that Homer’s mom was a leftist political activist also deepened Lisa’s connection to her family. Her free-thinking progressivism isn’t an anomaly; she just takes after her grandmother. Even following the character’s death, the show was somehow able to mine Mona Simpson for one last tear-jerking episode: the Inception parody “How I Wet Your Mother.” — JM McNab

33 Kirk Van Houten

Kirk Van Houten began his tenure as merely Milhouse’s nameless dad, but the Van Houtens’ separation in “A Milhouse Divided” cemented Kirk’s place in the pantheon of Simpsons icons. From Kirk’s failed attempt to sketch “Dignity” to his bachelor pad’s race-car bed to his painful efforts to launch a singing career with his “Can I Borrow a Feeling?” demo tape, Kirk exuded divorced dad energy more piteously than any other character in television history. — JM McNab

32 Nelson Muntz

When he originally debuted in Season One’s “Bart the General,” Nelson was just a generic school bully. Since that time, however, we’ve become familiar with his endearing sensitive side. He still wants to nuke the whales (“gotta nuke somethin’”), but he’s also a massive fan of crooner Andy Williams. Similarly, he still bullies his classmates, but he is a connoisseur of fresh fruit. (Nancy Cartwright has stated her favorite Nelson quote is, “The thing about huckleberries is, once you’ve had fresh, you’ll never go back to canned.”) Even Lisa saw his sensitivity and dated him briefly, sharing her first kiss with him. — Neil Arsenty

31 Lenny and Carl

Perhaps it’s unfair to group together two distinct characters who have been with the show since the first season, but Lenny Leonard and Carl Carlson are inarguably a duo (and perhaps, as some fans have noticed, more than just a duo). While the two nuclear-plant employees have mainly been relegated to background roles (so much so that Homer keeps crib notes on his hand reminding him who’s who), just think of how many classic episodes they’ve enriched, be it introducing Homer to the Stonecutters, or playing on the plant’s softball team. Lenny seems to have gotten more standout solo moments (such as his extreme plastic surgery or the moment in which it’s revealed that he lives in utter squalor), but these two clearly belong together. — JM McNab

30 Fat Tony

Originally conceived as a one-off character to be played by late character actor Sheldon Leonard, Springfield mob boss Fat Tony has popped up countless times since his initial appearance in Season Three’s “Bart the Murderer.” In all but one episode, Fat Tony has been voiced to perfection by Joe Mantegna, often “playing dumb” when authorities question him but also “playing menacing” when “dumb” fails. 

Those who haven’t watched the series in the last 13 years may not realize the character in recent episodes is not the same Fat Tony, but in fact, his cousin, formerly known as Fit Tony, but as the series treats the characters the same, so do we. “Who knew that Fat Tony was gonna resonate in the hearts and minds of the Simpsonites out there?” Mantegna opined to The A.V. Club years ago. — Neil Arsenty

29 Chief Wiggum

It’s remarkable that such a distilled representation of police corruption and mismanagement on television can be such an enjoyable pleasure to watch, but here we are. Chief Clancy Wiggum, like his son Ralph, took a few episodes to come into his own as the character he is today: the force of inept authority and gullibility, who can’t even pronounce the word “motive” much less figure it out in a case. But his delivery (expertly done by Hank Azaria) and his rotund gesticulation always brings a smile to our faces. — Neil Arsenty

28 Itchy & Scratchy

Name anything quite as synonymous with the show as this ultra-violent Tom and Jerry parody. While their psychotic cartoons would be hilarious enough, Itchy & Scratchy have also become Springfield’s version of The Simpsons — essentially the mouthpiece for the writers to comment on The Simpsons beyond just the show itself. — Warren Evans

27 Patty and Selma

When it comes to Marge’s chain-smoking twin sisters, Patty and Selma Bouvier, one is not complete without the other. Despite being total opposites when it comes to sexual orientation — with Selma a man-hungry multiple-marriage divorcee and Patty a closeted lesbian until Season 16 — their hatred of their brother-in-law Homer and love of MacGyver has provided fans with enjoyable running gags throughout the series. — Neil Arsenty

26 Barney Gumble

The Moe’s Tavern regular — not to mention the award-winning filmmaker of Pukahontas — Barney Gumble has had an eventful run on the show, becoming sober for several seasons before relapsing off-screen at some point. (An extra-tragic development considering that Barney was once a promising young college student before being corrupted by Homer’s beer-soaked influence). While “sober Barney” never truly clicked, he’s always been more than just a stock drunk character. Barney is a loyal friend to Homer, albeit with a competitive streak that gave us classic storylines like the Plow King/Mr. Plow conflict, and Homer’s NASA training camp showdown. — JM McNab

25 Superintendent Chalmers

As Simpsons writer Bill Oakley describes him, Superintendent Chalmers is the only sane man in Springfield, and that’s what makes him so funny. He manages to survive in this town because he knows how crazy everybody else is, and, as a result, he’s developed the perfect coping mechanism: indifference. The perfect foil for the habitually-lying Seymour Skinner, Super Nintendo Chalmers is the funniest straight man on the show. — Brian VanHooker

24 Comic Book Guy

Comic Book Guy is now such a fixture of The Simpsons that it’s become a joke in and of itself that everyone in Springfield just accepts that his name is “Comic Book Guy.” The proprietor of The Android’s Dungeon may have started as an unceremonious takedown of nerd stereotypes, but he’s since faced life-threatening health scares and enjoyed multiple romances. And as pop culture has evolved, so has society’s perception of Comic Book Guy. “Worst episode ever” used to be a joke at the expense of overzealous internet fans, but now it’s the meme through which people genuinely express their displeasure with art. — JM McNab

23 Groundskeeper Willie

The ultra-ripped groundskeeper of Springfield Elementary is always good for a laugh and had one of the best “Treehouse of Horror” segments ever when he became a Freddy Krueger parody. The proud Scotsman is a kilt-wearin’ maniac, that’s for sure, and he’s dancin’ like he’s never danced before. — Brian VanHooker

22 Maggie Simpson

Without ever speaking, Maggie has delivered some of the show’s most exhilarating sequences, such as the Great Escape-like jailbreak from the Ayn Rand School for Tots, and some of the most emotional moments. (Maggie’s first word and Homer’s “Do It For Her” sign still hit as hard today as they did way back when.) More recently, Disney has tapped Maggie to star in their series of streaming comedy shorts, usually crossing over with other Disney-owned intellectual properties. And let’s not forget that Maggie was the only one in Springfield brave enough to gun down Mr. Burns. — JM McNab

21 Mrs. Krabappel

While Bart’s teacher easily could have been crafted as a perfunctory antagonist for our bad boy hero, Edna Krabappel (played by the late, inimitable Marcia Wallace) was thankfully afforded a degree of depth, even sharing a certain soulful kinship with her most troublesome student. And while her divorcee status was occasionally played for laughs in early episodes, she ended up having some of the most meaningful romantic relationships in the series — falling in love with Woodrow/Gordie Howe, “making babies” in the janitor’s closet with Principal Skinner and eventually marrying Ned Flanders. — JM McNab

20 Santa’s Little Helper

Santa’s Little Helper is beyond important to the show. Going all the way back to the first episode, “Simpsons Roasting on an Open Fire,” his origin remains a key point of most people’s first experience with The Simpsons. Not only that, but his relationship with the entire family is an ongoing experience. Sometimes it’s a struggle, sometimes it’s happy and sometimes it’s just sad. If you need help being convinced of Santa’s Little Helper’s significance, watch “The Way of The Dog,” which puts you into his head like never before. Beyond that, his love for Bart could break anyone down. Good boy. — Warren Evans

19 Frank Grimes

Inspired by Michael Douglas’ character in Falling Down, Frank Grimes — or “Grimey,” as he liked to be called — was meant to represent what it would be like if an average person became associated with someone like Homer. Although most of his co-workers and friends are used to it, Grimes is dumbfounded by Homer’s achievements, despite his stupidity. His eventual meltdown from witnessing this ends up killing him, but Grimes was so popular with fans that the writers brought back his son to get revenge on Homer in a Season 14 episode, and we see Grimes’ ghost in Season 28. — Neil Arsenty

18 Milhouse Van Houten

Milhouse “THRILLHO” Van Houten’s beginnings were anything but auspicious. The unnamed, blue-haired best friend to Bart Simpson made his debut in a Butterfinger commercial and was initially designed for a Saturday morning cartoon project Matt Groening couldn’t get off the ground. Even when Milhouse finally became a full-fledged series character, he was still named after both Richard Nixon and a member of the Manson Family.

But since then, everything’s been coming up Milhouse! Most importantly, Milhouse’s best stories touch on relatable childhood emotions, from his parents’ separation to his first girlfriend to the time he moved to another city. Milhouse is irreplaceable — even with Mickey Rooney. — JM McNab

17 Grampa Simpson

Abraham “Grampa” Simpson (immortalized in meme form as the old man who yells at a cloud) is hands-down one of TV’s funniest characters. The now frequently-confused, elderly, Matlock-loving Abe is really nothing like Homer. We see in flashbacks that Grampa was a conservative hard-ass who drove his wife away and never fully understood his son — presumably all while wearing an onion on his belt, which was the style at the time. And while Grampa is always good for the occasional laugh, he also got to be a total badass in the “Flying Hellfish” episode because Grampa, like an onion, contains layers. — JM McNab

16 Ralph Wiggum

Love him or hate him, Ralph Wiggum is the most popular non-Simpson child on The Simpsons. It took him a few episodes to become the darling lack-wit we know today, and the best representation of his character remains his first major episode — Season Four’s “I Love Lisa.” He also might be the most quotable character on the show, so much so that the Bloodhound Gang wrote an entire song comprised of Ralph’s best lines. Nancy Cartwright, who voices him, feels he’s a fan favorite because “he can say anything and get a laugh. He’s a walking non sequitur.” — Neil Arsenty

15 Lionel Hutz

A true snake in the grass, always cutting corners and looking for the next big payday, Phil Hartman’s Lionel Hutz simply couldn’t get out of his own way. When thinking of the shady attorney, you undoubtedly have as many favorite lines from him as you do some of the highest-ranked characters featured here. And as far as episodes go, it doesn’t get much better than “Bart Gets Hit by a Car” or “Realty Bites,” where this ambulance-chaser really got to shine. — Warren Evans

14 Hank Scorpio

Guest star Albert Brooks has played a total of six characters in The Simpsons universe. For each, the producers gave Brooks complete freedom to improvise. They all have their moments, but the super-rich criminal mastermind (but super-nice boss) Hank Scorpio tops the list. Appearing in just one episode, “You Only Move Twice,” Scorpio was so popular that he almost returned as the main antagonist in The Simpsons Movie before being replaced by a new character, Russ Cargill, also played by Brooks. Scorpio has managed to unleash multiple meme-able moments, favorite quotes and three action figures, all from his lone appearance. — Neil Arsenty

13 Apu Nahasapeemapetilon

It’s hard to know where exactly to place Apu, considering that he’s the only main character to have been dropped from the show due to evolving cultural standards. As comedian Hari Kondabolu illustrated in his 2017 documentary The Problem with Apu, the character was basically the cartoon equivalent of a modern-day minstrel show. This wasn’t wholly without intent, either. Hank Azaria once admitted in an interview that he created the “annoying” Apu voice as an act of revenge after an Indian 7-Eleven clerk once yelled at him. 

The show’s half-assed, heel-dragging attempts to address Apu’s problematic nature prior to finally writing him out of the series also further soured the character’s legacy. But it would be disingenuous to pretend that Apu wasn’t a hugely important character to The Simpsons for the majority of its run, not just as the purveyor of the Kwik-E-Mart, but as a friend to the Simpsons and, eventually, a family man. Unfortunately, Apu’s prominence also perpetuated harmful stereotypes and fueled real-life schoolyard bullies. It’s unequivocally for the best that he got Poochied back to his home planet. — JM McNab

12 Waylon Smithers

Smithers is the best example of how The Simpsons has adapted to changing times. While the show is rarely ahead of the game — see the Apu entry above — it generally does the right thing eventually regarding representation and not reinforcing stereotypes. 

Originally, the joke about Smithers was that he was gay, and that’s pretty much it. While the early object of his affection being Mr. Burns made for some funny moments, the predictably stereotypical depiction of Smithers’ closeted sexuality is one of the things that dates the show’s early seasons. Fortunately, The Simpsons would eventually portray him as a proud gay man, offering him much more depth. — Brian VanHooker

11 Sideshow Bob

Bart’s greatest mortal enemy (in addition to Dr. Demento) is also among the show’s most enduring non-Simpson characters: Sideshow Bob Terwilliger, the homicidal snob voiced by Kelsey Grammer. Who doesn’t love Sideshow Bob? For the rake gag alone, the character is an all-timer. But Sideshow Bob also has one of the most colorful biographies of anyone on the show — multiple arrests, a reconciliation with his estranged brother Cecil (voiced, in a meta twist, by Frasier’s David Hyde Pierce), and then there was that time he briefly started a new life with an Italian wife and son. Currently, he’s living in an abandoned lighthouse, as is his wont. — JM McNab

10 Troy McClure

The perpetually washed-up actor Troy McClure initially seemed to be created just to spout hilarious titles of educational and self-help videos like Smoke Yourself Thin and Get Confident, Stupid!, but thankfully, the Simpsons writers loved Phil Hartman enough to give us an entire episode centered around the character (“A Fish Called Selma”). — Neil Arsenty

9 Moe Szyslak

Moe started off as a grumpy bartender — getting prank-called, watering down beer, charging for fumes — but he’s played an enormous role in many Springfieldians’ lives — especially Homer’s, Barney’s, Bart’s, Marge’s, Lenny’s and Carl’s. He steals recipes, gets a facelift, bans Homer from the bar, saves Homer from being beaten to death — the list could go on for the length of this article. — Warren Evans

8 Principal Seymour Skinner

The lonely, Steamed Hams-loving authoritarian spends his personal time making to-do lists and watching washing machines spin. While at work, he’s regularly getting duped by the kids and lying to his boss about how things are going. He also lives with his mother, who he’s still repaying for the food he ate as a child. Poor, poor Seymour. — Brian VanHooker

7 Mr. Burns

Perhaps the most despicable of all the characters on this list, Springfield Nuclear Power Plant owner Charles Montgomery Burns is responsible for the most heinous deeds in the Simpsons universe (including blocking out the sun for his own profit), but his lack of contemporary awareness continues to endear him to viewers. His original stacked company softball team involved old-timey players who had all died (“Alright, find me some good players! Living players!”), and he answers the phone like inventor Alexander Graham Bell (“Ahoy hoy!”). Even at his most evil, he makes us laugh as he makes Springfieldians cry. As a top character, we think he’s excellent. — Neil Arsenty

6 Marge Simpson

Marge deserves better than sixth place on this list, but we had to knock her down a few pegs because she was short-changed by the show itself for a good chunk of its history. When The Simpsons began, Marge was the typical TV wife/mother. She’s a sweet, doting, stay-at-home mom and the voice of reason for her idiot husband and hell-raising son. Because of this, she was easily the least funny member of the Simpson clan. 

This, though, has changed over time, with Marge being shown to be more than just a pun-loving nurturer. Her biggest, most interesting character flaw is her ignorance of the wider world and the fact that she can sometimes be behind the times. When her vulnerabilities have been explored to their fullest potential, Marge has shined, delivering a lot of fantastic episodes. That said, there’s still a part of the character trapped in June Cleaver mode. 

To change her now would be a betrayal of the character, and the Simpson family unit needs its voice of reason. The best The Simpsons writers can do to make Marge interesting is to challenge her — and themselves — which, thankfully, they’ve done with increasing frequency as The Simpsons has gone on. — Brian VanHooker

5 Krusty the Clown

The most merchandised of any non-Simpson in Springfield (both on the show and IRL), Krusty has remained a source of comedy gold. Whether gags about hometown celebrity status, aging bitter television stars, money-hungry shilling or the perils of working with children, Krusty covers all the bases. He may have bet against the Harlem Globetrotters (“I thought the generals were due!”) and let down his fans more times than they lead on, but he always finds a way to bounce back with his signature laugh in tow. — Chaz Kangas

4 Ned Flanders

Ned Flanders is undeniably a dork. He’s a bit uptight, a touch on the lucky side and constantly looks like he’s ready for church. So why do we love him? While there are so many things to dislike about his obsession with religion and his refusal to stand up for himself, there is also something overwhelmingly endearing about Flanders. He always wants to see the best in people — he can even find a positive side to mosquitos. 

We see Flanders constantly mistreated by Homer, but he continues to search for his neighbor’s better qualities. In reality, we’d all benefit from refusing to have our day ruined as Flanders does, and because of that, Flanders is pivotal to how we see the series. Plus, he has hands-down the best meltdown on the show. — Warren Evans

3 Bart Simpson

In the early 1990s, Bart straight-up was The Simpsons. His rebel posturing and obscene language (what kind of child says “hell” on TV?) led to a headline-grabbing, wildly controversial T-shirt fad, as well as countless licensed products, ranging from books to video games to juice boxes, all featuring the Bart Simpson brand. (A trend later parodied in “Bart Gets Famous.”)

In retrospect, what makes him a truly great character — and makes the moral blowback to his debut all the more ridiculous — is that Bart is a big old softie. Even in the episodes where Bart hatches nefarious schemes and wildly misbehaves, the stories frequently tend to wrap up with him learning a lesson and ultimately sharing a moment of tender reconciliation with a family member or friend. — JM McNab

2 Lisa Simpson

Most of you are probably surprised to see Lisa rank higher than her more popular, quoted and merchandised brother. Sure, she can be a little self-righteous, but when you really step back and look at the family, Lisa is the necessary counterbalance to Bart, Homer and Marge. She represents a level of maturity and awareness rarely seen in this universe and is the glue that makes the family dynamic work. Not only is she relatable, but she brings out the best in her bloodline. Stories featuring Lisa usually stick with us for a very long time, regardless of whether or not we quote them as often. — Warren Evans

1 Homer Simpson

There was never any question about whether or not the patriarch of the Simpson family would top this list. Homer J. Simpson — despite his basic stupidity — manages to be The Simpsons’ most complex character while also being the funniest, making him nearly every viewer’s favorite. 

Voice actor Dan Castellaneta said early in the show’s run that men would come up to him and say, “Aww, he’s my hero!” His response: “I think (that) is a pretty sad state of affairs for America.” Homer is a true paradox — simultaneously managing to be the best dad/son/husband/neighbor/friend and also the worst of all those things. But therein lies the rub, that paradox is pretty relatable. Basically, his faults are our faults. Which: D’oh! — Neil Arsenty