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50 Best Simpsons Characters Of All Time Ranked

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"The Simpsons" is one of the most enduring shows on television, a staple of broadcast television for well over 30 years. The animated series following a middle-class yellow family in Springfield, USA has over 700 episodes, and at this point the nuclear family has done just about everything and been everywhere you could possibly imagine. It has made a name for itself by packing in more references than you can imagine into every episode, balancing humor and heart better than the competition — all these decades later, still a strong suit.

But tales about the 5 Simpsons would have gotten old quick, so it's no secret that the show has endured for so long because of its head-spinning array of endearing, memorable Springfield residents. It's difficult to think of a show that has 50 characters, nevermind far more — and believe it or not, comprising a list of the 50 best "Simpsons" creations actually leaves out many more good ones. 

It's a tough job, but somebody's got to do it. Below, a ranked list of the 50 Best "Simpsons" characters of all time.

50. Lindsey Naegle

One of the hardest working ladies on "The Simpsons," Lindsey Naegle (Tress MacNeille) is always hustling for a paycheck. 

In her every appearance, Naegel appears with a brand career focus. Who could forget her vital work with SSCCATAGAPP, the anti-youth group better known as Singles, Seniors, Childless Couples and Teens and Gays against Parasitic Parents? Perhaps Naegle's business ventures haven't always been always huge successes, but every time she appears in "The Simpsons," she seems determined to assert herself in a new realm. 

Voiced by the great Tress MacNeille, Lindsay feels like she's 99 percent can-do spirit, one percent actual forethought. As her business card explains: "Lindsey Naegle: Does Everything."

49. Sherri and Terri

Which one is Sherri? Which one is Terri? Nobody has any idea, but quite frankly, it doesn't matter. Among the rare "Simpsons" characters who have been there since the very beginning (first appearing in 1989's "Simpsons Roasting on an Open Fire"), they may have started with brown hair that has become consistently more purple with each passing year but, like Bart, they've been stuck in the 4th grade for over thirty years. Just be thankful they aren't grey.

These little hellraisers (both voiced by Russi Taylor) probably wouldn't be very interesting as an individual student — but as a duo, they serve their purpose of always being up in Bart's business. It seems possible that one (or both) has a childhood crush on Bart, but if he likes one more than the other, he certainly isn't letting on.

48. Mrs. Hoover

Is any character in "The Simpsons" cast more relatable than Mrs. Hoover (Maggie Roswell)? This second grade teacher at Springfield Elementary is overworked and thoroughly exhausted, her once-eager optimism towards teaching replaced by the defense mechanism of a jaded worldview. teachers just don't get enough respect, whether they're working in the real world, or for Seymour Skinner.

The efforts of Mrs. Hoover seem to increasingly be to work less and get away from the students as quickly as possible (the sound of her car driving away while students remain in class is familiar for Simpsons fans). Other hobbies include smoking under the school's "No Smoking" sign, letting Ralph Wiggum teach, sleeping during class, and contracting Lyme disease.

If you want to best sum up Mrs. Hoover's mentality, think back to the time Lisa objected to so many films being shown during class. "Mrs. Hoover?" she asked. "Movies are a nice break, but couldn't we be doing something a little more challenging?"

"Probably," her indifferent teacher shot back.

47. Cletus Spuckler

"Some folk'll never eat a skunk, but then again some folk'll," the old song goes. "Like Cletus, the slack-jawed yokel!'

It's not every "Simpsons" character who gets their own theme (courtesy of "22 Short Films About Springfield," Season 7, Episode 21), but unapologetic hillbilly Cletus Spuckler (the first of many, many Hank Azaria characters on this list) is the anchor to some of the show's most amusing running gags, as Cletus and his wife Brandine (Tress MacNeille) engage in endless ways to remind us that they have no money, many kids, and questionable heritage.

"You are the most wonderful husband, and son, I ever had," Brandine once said to Cletus. We'll just leave that there.

Over the years, Cletus has evolved into more of a character and less of a redneck. Which is important, because he has to be a good role model for little Tiffany, Kendall, Kyra, Ian, Dubya, Melvis, Mary Not-Quite-Right, Embry Joe, Gitmo, Hunter, Rubella Scabies, Scout, Rumer, Dermott, Q-Bert, Gummy Sue and the rest.   

Most folk'll never lose a toe but then again some folk'll ... like Cletus, our beloved slack-jawed yokel.

46. Otto Mann

The coolest dude in Springfield, Otto Mann (the first of many, many Harry Shearer characters on this list) drives the school bus — just not very well.

A  gleeful sendup of the guys whose dreams of becoming a big-time rock star never quite worked out, Otto instead has become something of a burnout, hoping to get through the day without removing his beloved earphones and hopefully not running over any kids. Otto is extremely laid back, often to a fault, often content to sit back and listen to his favorite cassette tape: "Songs to Enrage Bus Drivers." Note, technology has moved past the cassette tape approximately 18 times since "The Simpsons" debuted in 1989; Otto has not.

Otto isn't a total failure, however; he conceals a genuine talent when it comes to playing the guitar. In one memorable moment, Bart gave Otto a guitar while insisting it was broken — but Otto played it brilliantly, reminding viewers that he's got a lot depth than merely being a stoner.

45. Rod and Todd Flanders

Okay, they're a little easier to differentiate than Sherri and Terri, but not that much. Ned Flanders' boys have seemingly interchangeable personalities, are both really hung up on issues of religion, avoiding sin and denying themselves of things, and they both seem to think next-door neighbor Bart is the devil. Which sort of makes sense — after all, Bart's dad killed their mom

While Rod (Pamela Hayden) and Todd Flanders (Nancy Cartwright) are two distinct characters, it feels impossible to choose one over the other, so the brothers occupy this spot on the list together. The pair play amazing games like sitting still, where they ... well, you get the idea. The boys are two of the most well-behaved kids in the universe, but they occasionally transgress, largely because of Bart. One of their funniest moments involves them being exposed to sugar for the first time, causing them to immediately shed their good boy personas. They have to tread a fine line though, because if they misbehave, they might lose out on their bible stories.

44. Kang and Kodos

If nothing else, these two occasionally-glimpsed aliens provided "The Simpsons" with one of their greatest lines, one that still lives on in bumper stickers and t-shirts every election cycle: "Don't blame me, I voted for Kodos."

The lovable duo of Kang (Shearer) and Kodos (our first of many Dan Castellaneta characters) are from Rigel 7, representing a menacing presence on the show. As such, they have become a staple of the beloved "Treehouse of Horror" Halloween specials. What you might not realize is they are sisters with the last name "Johnson" — what you almost certainly realize is that the "How To Cook For Forty Humans" gag (from the "Hungry are the Damned" segment of the original "Treehouse of Horror," Season 2, Episode 3) is one of the all-time funniest in "Simpsons" history.

Forever scheming to take over the Earth, the closest they've ever come is the "Citizen Kang" segment of "Treehouse of Horror VII"( which gave us the immortal "Don't blame me" line) — but since every "Treehouse" has its own one-off continuity, these Quantum Presbyterians (although, to be fair, Kodos later claimed to be Jewish) seem destined to reset their efforts every time. 

43. Fat Tony

Crime boss Fat Tony ("Criminal Minds" star Joe Mantegna) is the king of playing innocent. When questioned by Police Chief Wiggum, he glibly responds "What's murder?" 

Fat Tony is a great character because we all know what he really does, but he so rarely admits to it. This is perhaps most memorably demonstrated in  "The Mook, the Chef, the Wife and Her Homer" (Season 18, Episode 1), when the Simpsons befriend his son Michael, leading to Tony participating in their carpool — and employing Milhouse's Garfield binder to kill a bunch of guys from the Calabrese family, "My arch-enemies in waste-management."

Of course, Tony has orchestrated many memorable schemes operating outside the long-arm of the law, including his infamous "Legitimate Businessman's Social Club" plan to make money off the schools by replacing their beverages with rat's milk. Love him or hate him, you'd better listen to Fat Tony, or else you might end up like his wife who was "whacked by natural causes."

42. Superintendent Chalmers

Perhaps best known by Ralph Wiggum's name for him — Super Nintendo Chalmers — this endlessly agitated, hopelessly naive school official serves as the principal antagonist for principal Skinner. And if nothing else, he's remembered for the iconic, endlessly-memeable "Steamed Hams" segment (also from "22 Short Films"). 

Few characters in television are so fondly recalled by a single word, but shouts of "SkinNER!" and all its variations (SkimMER!) never fail to amuse. Chalmers is the sort of person who shouldn't have power, but he does, and he takes great pleasure in finding fault with Seymour, who he for some reason nonetheless continues to employ. 

He's also got some amazing dance moves — particularly when "Footloose" is playing.

41. Frank Grimes

The focal point of one of the greatest "Simpsons" episodes of all time ("Homer's Enemy," Season 8, Episode 23), tenacious, hard-working Frank "Grimey" Grimes never had it easy. And when he met Homer Simpson, things only got more difficult.

Voiced by Hank Azaria, Grimes was born from "Simpsons" writer John Swartzwelder imaging how difficult it would be to work alongside Homer, whose every act of ineptitude seems to only reward him. When a reporter later called the grim ending of the episode (where Homer falls asleep during Grimey's eulogy) heartless, Swartzwelder defended the classic script.

"Grimey was asking for it the whole episode," he said. "He didn't approve of our Homer. He was asking for it, and he got it. Now what was this you were saying about heart?"

Hired after Mr. Burns sees a news story on Grimey's difficult life challenges, insisting he wants a "self-made man," Grimes begins work at the nuclear power plant hoping to put his hard-earned degree in nuclear physics to good use. Immediately stunned by Homer's incompetence — and his blessings of a good home, a loving family and food on the table — Grimey comes to symbolize the disillusionment of the American Dream, ultimately realizing that hard work offers no guarantees of satisfaction in life. 

This makes him one of the most tragic characters to ever appear on the show, punctuated when he electrocutes himself in an attempt to show what it would be like if everyone behaved like Homer — dying in a state of madness and disbelief. In 2021, we picked "Homer's Enemy" as the best Simpsons episode ever, and still find it difficult to argue the point.

40. Bleeding Gums Murphy

Another character with limited appearances in "The Simpsons" (and none, really, since his death in Season 6), legendary saxophonist Bleeding Gums Murphy (Ron Taylor) nevertheless has made his impact known, particularly as an ongoing inspiration for Lisa, his prized protege. 

In "Moaning Lisa" (Season 1, Episode 6), Murphy helped impart the magical power of music on a depressed Lisa, who channeled her emotions into playing the blues. Lisa later encountered Murphy in the hospital in "'Round Springfield" (Season 6, Episode 22), where Murphy imparted some valuable wisdom to the youngster. Later appearing in the clouds, he jammed with Lisa one last time.

Upon his death, Bleeding Gums left Lisa his saxophone. These days, he is occasionally glimpsed via a photo in Lisa's room or some such reference — and he seems to have a heavenly relationship with Billie Holiday. 

39. Agnes Skinner

The first time we saw Agnes (MacNeille), she seemed like a lovely lady, playfully calling her son Spanky and behaving like a sweet grandmotherly type. After a Bart Simpson prank had him putting a cherry bomb in her toilet, however, Agnes would never be the same.

Now a curmudgeon who tries to control her adult son's every breath, she's one tough cookie. Agnes is also no stranger to romance, having struck up passionate relationships with both Chalmers and Comic Book Guy (the two meet at a class called "How to Make Friends"). Always eager to knock her son down a peg, it's best to stay out of her way.

38. Mayor Quimby

No character knows scandal more intimately than beleaguered Mayor Joe Quimby (Castellaneta). Quimby seems completely incapable of refusing a bribe (perfectly willing to even accept those in bags with a giant dollar sign on them), though that's probably because he's far more interested in money than he is in fulfilling his duties as a public servant. 

Mayor Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell The Edge Quimby Jr.is also frequently caught in bed with just about everybody but his deeply frustrated wife, as nobody gets around town quite like Quimby. Ultimately, the Mayor will do whatever it takes to serve himself, including helping Marge get out of jail so women would continue to vote for him. He's a scathing parody of the corrupt politician, but it sure is fun to watch him bend the law. Vote Quimby!

37. Kent Brockman

America has always valued news anchors to deliver the stories they need to keep informed. In Springfield, that duty is held by Kent Brockman (Shearer), a proud Stonecutter and the first to welcome our new insect overlords.

As the anchor of Channel 6, Brockman is the reliable voice the citizens of Springfield depend on, and he provides fodder for many memorable "Simpsons" moments. He once realized he won the lottery on-air — quitting instantly. He used his bully pulpit to urge a ban on all music. But as he has dutifully reported, dozens of people are gunned down in Springfield each day — and Kent is there to cover it all. 

36. Gil Gunderson

Originally based on Jack Lemmon's sad-sack salesman in "Glengarry Glen Ross," ol' Gil Gunderson (Castellaneta) has been trying since "Reality Bites" (Season 9, Episode 9) to hold down a steady job. That episode came out in 1997, which tells you how unlucky the guy is. 

Gil is always reaching for the stars, but can never quite grab one. His wife cheats on him (he offers words of support), he was forced out of the Springfield Men's Mission once because he'd overstayed their six month occupancy limit, and his father killed himself by jumping out a first-story window. But despite life repeatedly kicking Gil in the teeth, there is something inspiring about the way he never gives up.

35. Dr. Nick Riviera

"Hi everybody!," announces Dr. Nick Riviera (Castellaneta) whenever he enters a scene. And once, in "The Simpsons" movie, he famously gave a cheery "Bye everybody!" right before dropping dead. But don't worry, somehow he survived — undoubtedly, someone else must have performed the surgery.

Forever in the Springfield shadow of the superior Dr. Hibbert, Dr. Nick is a dubious doctor with a highly questionable medical degree, but he distinguishes himself from the competition by being cheaper. He advertises on TV in ridiculous infomercials, flaunting his medical degree from the Hollywood Upstairs Medical College — but if you choose to be a patient, don't be surprised to wake up and discover he has accidentally swapped your arm with a leg. 

Dr. Nick's unfailingly cheery disposition as he peddles miracle cures and watches videos on how to do open-heart surgery is funny to us, if not always to his patients. If you're feeling brave, step on up and call his clinic in the Springfield Mall at 1-600-DOCTORB. And don't forget: the B is for bargain.

34. Comic Book Guy

If Comic Book Guy (Azaria) saw that he only ranked at #34, he'd undoubtedly say "Worst list ever!" A constant complainer and super-nerd, Comic Book Guy owns The Android's Dungeon, a comic book and card shop that Bart and his friends frequent. 

Loosely based on Ain't it Cool News online movie news pioneer Harry Knowles, the character is a loving commentary on obsessive fan culture. Did you know that his real name is Jeffrey Albertson? That he has a degree in folklore and mythology? Or that he was Moe Szyslak's first kiss?

Comic Book Guy is a riddle wrapped inside and enigma, gaining even more complexity in Season 25 when he married Kumiko (MacNeille). Even he would have to admit, it was the best wedding ever.

33. Sideshow Mel

Springfield's resident thespian, Sideshow Mel (Castellaneta) is a professional clown, working as Krusty the Clown's sidekick on his television show. He considers himself a great actor, but let's be real: he's just the guy who took over for Sideshow Bob. 

When the cameras are off, Mel is a completely different person, speaking in a dignified British accent, and would strongly prefer delivering resplendent Shakespearian monologues rather than taking a pie to the face. Mel is a great character because, despite the green hair and bone, he's very grounded. Who else could deliver a line like "Look! It's internet buffoon Angry Dad!" with such grace and credibility?

Like many Springfield residents, Sideshow Mel has greater ambitions than the role he finds himself in. And he's determined to make something of himself, even if he has to use every last bone in his body.

32. Nelson Muntz

A school bully with a surprising heart of gold, Nelson Muntz has a simple catchphrase we can all use in our daily lives — shouting "Ha ha!" whenever somebody else has something go wrong. 

Of course, Ian (the extremely tall man) once made Nelson pay for his laughs, but he clearly didn't learn his lesson.

Once a fairly one-dimensional villain, over the years "The Simpsons" have developed Nelson as a surprisingly sensitive soul. This was used particularly well in "Lisa's Date with Destiny" (Season 8, Episode 7), where Nelson began dating Lisa. It revealed a surprising depth to the bully — at his core, he's just looking to be loved and accepted, and uses bullying as a defense mechanism.

31. Helen Lovejoy

Are you thinking of the children? If the reverend's wife, Helen Lovejoy (Maggie Roswell) is around, you'd better be! The ultimate town gossip, Helen is always looking to stir up some drama amongst the citizens of Springfield, and is perennially available in town hall meetings to shout "Won't somebody think of the children!?!

Despite this insistence that she always cares for the kids, she doesn't seem to pay much attention to her own, as her own daughter Jessica (Meryl Streep) is quite the troublemaker. Sure, Helen is one of the more conniving and downright nasty characters in "The Simpsons," but it sure is fun when she pops up with her signature line.

30. Luann Van Houten

Luann Van Houten (Maggie Roswell) seemed like a stuck-up housewife upon first impressions, and she has always been highly protective of her son Milhouse (Pamela Hayden). Who can forget the time she dragged Bart out of their house by his ear after he swore in "Marge Be Not Proud?" 

But in "A Milhouse Divided" (Season 8, Episode 6), Luann stepped out from the shadows and divorced her husband Kirk (Azaria) after a disastrous game of Pictionary. While Kirk really struggled with the dissolution of his marriage, Luann took to single life like a moth to a flame, providing inspiration for all those looking to break out and try something new.

29. Carl Carlson

To work somewhere like a nuclear power plant, it seems you'd have to be pretty calm, cool, and collected — which is exactly why Carl Carlson (Hank Azaria until 2020, now Alex Désert) is so good at his job. 

With so much chaotic, unpredictable energy among the residents of Springfield, Carl is a true breath of fresh air (even if many fans can't tell you which one is Carl and which one is Lenny, his ever-present BFF). Carl might be a quiet guy, but watch out when he gets rolling; in "Pygmoelian" (Season 11, Episode 16), he makes everyone at Moe's cry with his cutting observations. For the most part, though, Carl is an effortlessly charming guy, and even got his own episode with "The Saga of Carl" (Season 24, Episode 21), which explored his Icelandic heritage.

28. Lenny Leonard

Okay, Lenny and Carl are side-by-side on this list. But it's not because they're essentially the same character, no, it's ... that we thought it would it be appropriate to put the two best friends on the show next to each other. Yeah, that's it.

Carl and Homer's dear friend Lenny Leonard (Shearer) works alongside his pals at the Springfield Nuclear Power Plant. Unlike Carl, Lenny isn't quite as chill as his best friend, but that's probably because one of the show's funniest running gags involves various things getting stuck in his eye — even though he's not supposed to get things in his eyes! 

The injury-prone Lenny has a mysterious relationship with Carl that may or may not be more than just friends, as distinct homoeroticism runs throughout their dynamic, though it's never confirmed whether or not the two are romantically entwined. In "Half-Decent Proposal" (Season 13, Episode 10), Lenny points out Mount Carlmore, an enormous mountain with Carl's likeness carved into it that Lenny himself made "one wonderful summer." Because sure, friends do that.

27. Dr. Hibbert

Want to feel old? In the character's early days, Dr. Hibbert was portrayed as a friendly jab at Bill Cosby — who was the ratings king on TV at the time via "The Cosby Show," and had a similar affection for overly-busy sweaters. At the time, FOX had moved "The Simpsons" to Thursdays, opposite arguably the most popular show of the '80s, and the media was making a big deal of the "Bill vs. Bart" rivalry. Decades later, the Cosby story has taken a decidedly different turn — but Dr. Hibbert is still here. 

Dr. Julius Hibbert (Harry Shearer until 2021, now Kevin Michael Richardson) is the most reliable doctor in Springfield. That's probably not a great sign for the people of Springfield, as Hibbert isn't exactly perfect; in "HOMR" (Season 12, Episode 9), Hibbert admitted he had never noticed that Homer had a crayon lodged in his brain, because he would always cover that part of the x-ray with his thumb. 

Still, he's a lot more reliable than Dr. Nick. Hibbert is best loved for his charming nature and relaxed candor, which occasionally jumps into super-serious mode — he is a doctor, after all. But if you're going to get bad news from a doctor, it makes things better if he chuckles afterwards, right?

26. Chief Wiggum

Now this list is getting to the point where it's tempting to not talk about characters, so much as just post a bunch of classic quotes from them.

"The ring came off my pudding can!"

"Uh, you've got the wrong number. This is 9-1 ... 2."

"You know you're not suppose to go in there. What is your fascination with my forbidden closet of mystery?"

"Mrs. Simpson, I have some bad news; your husband was found DOA ... Oh, wait, I mean DWI. I always get those two mixed up."

"If Ralph is stuck in something, press one. If something is stuck in Ralph, press two."

Coming across as some sort of hybrid between all-time-great character actors Charles Durning and Edward G. Robinson, Chief Clancy Wiggum (Azaria) is the overweight, disbelieving, donut-savvy Springfield crime-stopper. Listing just one-tenth of Wiggum's mistakes would take ages, but he's particularly prone to letting crimes take place directly behind him, or even right in front of him. he is frequently caught with his pants down.

If it wasn't for the vastly more competent police officer Lou (Désert) — who acts as the Penny to his Inspector Gadget —  the cops in Springfield would likely never arrest anyone. While he may be a bumbling fool, he's incredibly funny, and the way he still dotes over his lost-cause son Ralph is very sweet — as is his love for Bob Marley.

25. Patty Bouvier

The chain-smoking Patty Bouvier (Julie Kavner) is typically seen alongside her best friend and twin sister Selma (also Kavner), but the two are distinct characters in their own right. The ladies are known for their snideness and generally pessimistic worldview, delighting in their sadistic duties at the DMV, but Patty is definitely the more jaded of the two. 

In "There's Something About Marrying" (season 16, Episode 10) Patty reveals to Homer and Marge that she's a lesbian. Though she's best known for being negative and coming up with creative insults for Homer, Patty was finally given some genuine depth with the revelation, and became all the more fascinating for it.

24. Selma Bouvier

The eldest of the three Bouvier sisters, Selma takes great pleasure in barely caring about her job at the DMV and insulting Homer at every opportunity. 

Selma has had a number of romantic trysts with various men in Springfield, and she's been through a remarkable six marriages to Sideshow Bob (Kelsey Grammar), Troy McClure (Phil Hartman), Disco Stu (Hank Azaria), Lionel Hutz (Phil Hartman) and more. Each marriage seemed worst than the last (though none worse than Sideshow Bob, who did try to murder her), and so the Selma character has become increasingly empathetic as a woman who just wanted some love in her life. Thankfully, she has found great joy in her adopted daughter Ling (Nancy Cartwright), who she traveled to China to adopt in "Goo Goo Gai Pan" (Season 16, Episode 12).

23. Martin Prince

Like the male version of Lisa Simpson, Martin Prince (the phenomenal Russi Taylor) is Bart's schoolmate and a bona fide teacher's pet, always prepared with the correct answer. As a result of this, he's often a target for Nelson's bullying. 

Despite his joyful, flamboyant attitude, Martin has always struggled to make friends, an issue that was explored in "Grade School Confidential" (Season 8, Episode 19). It opens with Martin holding an extravagant birthday party for his friends, including a giant ice sculpture shaped like himself and a mathemagician, but things go awry when food poisoning sends most of the kids to the hospital.

22. Barney Gumble

Alcoholics are rarely funny, but Barney Gumble (Castellaneta) is so far gone at this point that all you can do is remind yourself he's just a cartoon character and enjoy the laughs.

Boasting a burp heard 'round the world, Barney was once a promising student on the path to Harvard before Homer introduced him to beer while studying for the S.A.T.'s, which led to a lifelong struggle. He also has the unexpected gift of an angelic voice, best heard while he fishes for spare change around the toilets of Moe's Tavern. Prone to starting fights with professional athletes including baseball Hall-of-Famers and heavyweight boxing champions, Barney has even been known to do battle with his best friend – all in the name of a little healthy competition.

Barney can also be sensitive and introspective, as seen in "A Star Is Burns" (Season 6, Episode 18), when he makes an emotional black-and-white film about his alcoholism. He's a deep, sensitive soul — and he's also the world's worst designated driver.

21. Groundskeeper Willie

It's time to get greased up, because Groundskeeper Willie (Castellaneta) is next on the list. Springfield Elementary's janitor and groundskeeper, Willie is distinctly Scottish and stands out with his very thick accent and red hair. 

Willie is devoted to Scottish culture and mannerisms, made abundantly clear when he attempted stand-up comedy wearing a kilt and bagpipes while talking about the difference between golfers in north and south Edinburgh. Willie lives in a shed on the school grounds, battles his arch-enemy Sheamus, and selling haggis as a side hustle. Willie's hobbies include nips and naps, romancing Inga, and channeling Sharon Stone.

Although there have been countless brilliant Groundskeeper Willie moments, he's rarely been as brilliant as in "Lard of the Dance" (Season 10, Episode 1), where plenty of grease-related incidents (including the imperilment of his "retirement grease") made for some big laughs.

20. Troy McClure

"You may remember me from..." are the signature words that would often introduce actor Troy McClure (Phil Hartman) at every opportunity. If McClure had an IMDb page, it would be one of the most prolific lists of performances around. Among his memorable film titles:

"The Boatjacking of Supership '79"

"The Contrabulous Fabtraption of Professor Horatio Hufnagel"

"Dial M for Murderousness"

"Give My Remains to Broadway"

"Hydro, the Man With the Hydraulic Arms"

"The Muppets Go Medieval"

His finest moment, however, was undoubtedly his performance as Dr. Zaius in the musical "Stop the Planet of the Apes, I want to Get Off!"

Although McClure seemed to be in everything from television and movies to infomercials and documentaries, he really became a part of the Simpsons' lives in one of the show's best episodes "A Fish Called Selma" (Season 7, Episode 19), where McClure revealed that he had a "romantic abnormality" that results in a romantic love of fish, providing a very funny parody of absurd celebrity tabloids.

19. Reverend Lovejoy

The Reverend at the First Church of Springfield, Timothy Lovejoy (Shearer) came to Springfield excited and eager to preach the word of God to his constituents. Then came Ned Flanders, whose constant (and we do mean constant) calls and questions wore Lovejoy down a great deal, even causing him to curse. 

While he remains a devoted servant of the lord, it's apparent that he'd rather be playing with his remote control trains. Lovejoy is always grappling with trying to get the people of Springfield interested in the church, as folks like Homer often sleep through his sermons and would rather be anywhere but church. Lovejoy's steadfast determination in the face of adversity has always impressed those around him, and the oft-exasperated reverend is one of "The Simpsons" great characters.

18. Lionel Hutz

A lawyer who seemed to have no comprehension as to what a lawyer actually did, Lionel Hutz (Phil Hartman) was one of the most effortlessly hilarious characters on "The Simpsons." 

"Mr. Simpson," he once insisted, "this is the most blatant case of fraudulent advertising since my suit against the movie, 'The Neverending Story'!"

"Can you imagine a world without lawyers?" once asked Hutz, who then imagined people all over the world holding hands in harmony, which caused him to shudder in horror. He may not have been able to spell guilty, and he may not have always worn pants, and he may not even have known what a recess was, but Hutz never stopped hustling to try and get the job done, even if he'd likely never succeed. Like McClure, when Hartman was murdered in 1998, "The Simpsons" officially retired the character in his memory. The passing of the versatile comedy legend was a shame for so many reasons, one being that the Hutz character would have inarguably yielded so many more classic lines and moments for viewers in the ensuing decades.  

17. Maggie Simpson

The youngest member of the Simpson family, Maggie has only spoken a few rare times over her time over 700-plus episodes, but she still manages to be an integral character on the show. Maggie has a surprising propensity for aggression, likely thanks to the influence of violent television, and has tried to kill Homer on multiple occasions, using a mallet and pencil to terrifyingly funny effect. Then, of course, there's her arch-enemy the unibrow baby

Though Homer occasionally forgets who Maggie is, or locks her in a newspaper box, her physical comedy is some of the finest the show has to offer. Never underestimate this sweet-faced, pacifier-sucking baby, as she just might be the most lethal character on the show. 

16. Waylon Smithers

A lackey desperately in love, Waylon Smithers (Shearer) is the personal assistant to Montgomery Burns (also Shearer) at the nuclear power plant. His love for Mr. Burns has occasionally reached uncomfortable levels, and at least once nearly resulted in him dying, but he's always there to help his employer.

After years of games between the "Simpsons" writers and audience, Smithers finally came out as gay in "The Burns Cage" (Season 27, Episode 17). Thankfully, the long-suffering character was freed from hopelessly pining over his boss, as one of the best recent episodes, "Portrait of a Lackey on Fire" (Season 33, Episode 8) found Smithers finding love with his new boyfriend Michael de Graaf (Victor Garber).

15. Ralph Wiggum

If charm was all it took, Ralph Wiggum would probably be at the very top of this list. The adorable student in Lisa's second-grade class has aspirations of being "a principal or caterpillar," and when he finds out he's failing English, he memorably responds: "Me fail English? That's unpossible!" 

Ralph has been a standout character ever since the early days of "The Simpsons." In "I Love Lisa" (Season 4, Episode 15) he declares his unyielding adoration for Lisa, who does not reciprocate and ends up devastating Ralph on live TV. Don't feel too bad for Ralph, though, as despite his learning difficulties he managed a pretty successful presidential campaign in "E Pluribus Wiggum" (Season 19, Episode 10). 

14. Edna Krabappel

It takes a pretty fantastic character to be instantly recognizable from a single syllable, but the cutting "Ha!" of Edna Krabappel (the late Marcia Wallace) became the stuff of legend. 

Krabappel was the fourth-grade teacher at Springfield Elementary, and as Bart was in her class, the two regularly clashed. While it seemed that Edna had no real interest in teaching and was rather heartless, her sensitive core got exposed in the beautiful "Bart the Lover" (Season 3, Episode 15), expanding the Krabappel character an exposing her as a lonely but caring woman who dreams of a passionate love that eludes her. 

Ultimately, Edna had a number of romantic rendezvous with Principal Skinner before eventually marrying Ned Flanders, which lasted until her unfortunate death.

13. Abraham Simpson

The undisputed leader of telling you how things were back in his day, Grandpa Abraham Simpson (Castellaneta) loves nothing more than to tell a long-winded story about his past — and perhaps, getting angry at clouds.

Through flashbacks, we've learned that Abe was very different when he was younger, and was also very difficult on his son Homer growing up. Abe has a lot of backstory, much of it courtesy of his experience in the war. Abe's attempts at love have sometimes been heartbreaking, never really panning out; the closest he got to true love was with Marge's mother Jacqueline Bouvier (Julie Kavner) in the great "Lady Bouvier's Lover" (Season 5, Episode 21). To paraphrase Grandpa: He used to be with it, but then they changed what it was.

12. Sideshow Bob

When it comes down to it, Sideshow Bob really only wants one thing: to kill Bart Simpson. He even has a tattoo that reads "Die, Bart, Die" on his chest — though according to Bob, it's merely German for "The, Bart, The." 

Focal point for one of the greatest jokes in "Simpsons" history, Bob (Kelsey Grammer) appears every few seasons to wreak havoc on the Simpsons in his attempts to take out Bart once and for all. Underneath his sinister exterior lies a consummate professional who loves to perform, which Bart takes advantage of in the tremendous "Cape Feare" (Season 5, Episode 2). Will Bob ever kill Bart? There are obvious reasons why "Simpsons" fans hope not, but a secondary one might be that we wouldn't have Bob pursuing his mission any longer.

11. Charles Montgomery Burns

Every great story needs a villain, and none are more delightfully evil than Charles Montgomery Burns, Springfield's literal and figurative cartoonish big bad. 

Burns (Shearer) is extraordinarily wealthy and old (one joke revealed his social security number to be 000 00 0002), and he runs the Springfield Nuclear Power Plant. When not curling his fingers together and sinisterly muttering "excellent," he's releasing the hounds on anyone who dares ask for assistance of any kind. He's also callously cruel to his long-suffering assistant Smithers, and is always scheming to add more to his endless piles of wealth. One of the character's best "Simpsons" episodes, "Rosebud" (Season 5 Episode 4) used a "Citizen Kane"-narrative framework (and gimmick) to explore Burns' childhood, and is well worth a revisit.

10. Krusty the Clown

"Hey hey, kids!" It's Krusty the Clown, making his way to a top 10 spot on our greatest Simpsons characters list. There are few things "The Simpsons" do better than deconstructing types, and the show has had a fantastic time exploring the backstory of this clown and children's TV entertainer. 

Krusty (Castellaneta) is beloved by pretty much every child in Springfield, none more so than Bart, who idolizes him despite his plethora of trust, substance abuse, honesty, morality and credibility issues. Krusty has a lot of untapped childhood trauma from his difficult upbringing, with a deeply religious Rabbi for a father (the superb Jackie Mason), who deeply disapproved of Krusty going into comedy. Despite his endless shortcomings, Krusty is still a funny, charming, and passionate presence that "The Simpsons" is all the better for having.

9. Apu Nahasapeemapetilon

The proprietor of Springfield's finest convenience store, the Kiwk-E-Mart, Apu Nahasapeemapetilon (formerly Hank Azaria, who has yet to be replaced) always welcomes customers with a cheerful smile. 

Apu found love with his arranged wife Manjula, who ended up giving birth to octuplets, keeping Apu tremendously busy. He's also a gifted musical talent, as showcased in the catchy song "Who Needs the Kwik-E-Mart?" Though the character has recently come under a great deal of criticism for his perceived portrayal as a stereotype, Apu still remains one of the most heartfelt, hilarious characters to ever be in "The Simpsons."

8. Moe Syszlak

The world's loneliest bartender, nobody does it quite like Moe Syszlak (Azaria). Whether he's unknowingly threatening the life of Bart over his relentless prank calls to Moe's Tavern, inventing Flaming Moe's, bowling with the Pin Pals, or having hot oil poured onto his head while attempting to operate a family restaurant, Moe is one of the most consistently funny characters in a show filled with them. 

Moe has a lot of heart too; he not-so-secretly yearns to be with Midge (um, Marge), looks to the Sears catalog for companionship, and is seen on multiple occasions tearing up while reading classic literature. Hanging out with Moe ("or as the ladies like to call me ... hey you behind the bushes!") could get you shot, raided, screamed at, part of an angry mob — or with a bar tab that needs to be calculated by NASA. Just, whatever you do, make sure you don't eat anything from his pickled egg jar

7. Bart Simpson

The ultimate prankster extraordinaire and the bane of Principal Skinner's existence, 10-year-old Bart Simpson (Nancy Cartwright) is the eldest child of the Simpson clan. He's a nightmare for authority figures, he's an underachiever (and proud of it), and his rebellions have put him, his best friend Milhouse, and his family into worlds of trouble — like the time he managed to infuriate the entire country of Australia. But at least he's an equal opportunity offender: He's mooned the American flag, albeit accidentally. Hey, the kid has been a prankster since he was ten minutes old. 

But the mischievous Bart has a soft side too, and world-class episodes like "Bart Sells His Soul" (Season 4, Episode 7) and "Marge Be Not Proud" (Season 7, Episode 11) showcase Bart's sensitive side, reminding us that over 700 episodes he has become a well-rounded, surprisingly sensitive character. Bart has countless moments with all of his family members, but the most memorable tend to come from his relationship with Homer. 

Some of the funniest moments of the show come from Bart pranking homer, and Homer strangling Bart as a result. Ultimately, Bart taught a generation of kids to stand up to authority with a passionate rallying cry of "Eat my shorts!" So thanks, Bart, for inspiring the rebel within us all.

6. Seymour Skinner

The beleaguered head of Springfield Elementary School, Principal Seymour Skinner (Shearer) hasn't had it easy. He suffers under the severe budgetary restrictions of public education, his relationship with his mother seems to be one step away from Norman Bates territory, his automobile situation is pathetic, and he is prone to the occasional flashback to Vietnam ... particularly when it involves memories of Johnny ... JOHNNY!

These days, Seymour spends his days battling a far younger, but no less ruthless adversary: Bart Simpson, the terror of Springfield Elementary. "If life has taught me one less repeatedly," he has said, "it's to know when I'm beaten." Oh Seymour, cheer up: you can always cook up some Steamed Hams and go for a ride in your Camry.

5. Milhouse Van Houten

On this list, everything really is coming up Milhouse! The only child of what's left of the Van Houtens (and he's got the scars to prove it), Bart's impressively-eyebrowed best friend is hopelessly in love with Lisa, allergic to almost everything, and really needs to be kept away from sugar

Milhouse (Hayden) may be desperate to please but is so rarely able to do so; nevertheless, he's Bart's ride-or-die for road trips, evading the feds, and pranks. The dynamic of their relationship shifted briefly when Milhouse got the upper-hand in "Bart Sells His Soul" (Season 7, Episode 4), possibly the greatest episode "The Simpsons" have ever produced on the topic of religion, and one that has inspired books as well as college professors

Through it all, Milhouse is an incredibly good sport when everything is crumbling around him. The ultimate tragicomic child, nobody does it quite like this little blue-haired rapscallion.

4. Ned Flanders

Hi-diddly-ho, neighborino! Everyone's favorite Christian father, Ned Flanders (Shearer) is the most surprisingly funny character on the show. 

His distinct way of speaking, adding lots of iddily, oodily and diddily's to words, have made him a legend, inspired at least one heavy metal band, and minted dozens of quotable "Simpsons" lines. But at his core, he's an exceptionally loving father and a devoted husband. 

Ned is one of the more unapologetically sexy characters on the show, as his washboard abs and tight buns (which caused Homer's famous "stupid, sexy Flanders!" line) are always an off-the-wall surprise. When faced with adversity, this mustachioed proprietor of the Leftorium (which is now, sadly, no-morium) is always trying to do his very best. 

Deep down, Flanders can be a tragic character, as both of his beloved wives, Maude Flanders (Maggie Roswell) and Edna Krabappel have passed away. In the face of tragedy, however, Flanders still manages to be a guiding beacon of light for his children and everyone around him – except, of course, Homer.

3. Lisa Simpson

The saxophone-playing wunderkind of the Simpson family, eight-year-old Lisa (Yeardley Smith) is their smartest child. Though living in the shadow of the hyperactive Bart would be difficult for any child, this middle child shines bright.

While Bart rebels through pranks, Lisa rebels against her family genes by working so hard at school. She's never afraid to voice her beliefs and fight for what's right, particularly in two of the best episodes focused on the character: In "Mr. Lisa Goes to Washington" (Season 3, Episode 2), she discovers the harsh truths of American politics; in "Lisa vs. Malibu Stacy" (Season 5, Episode 14), she designs a new doll to challenge the vapid Barbie-inspired Malibu Stacy. 

While those are two of the series' heavier episodes, Lisa is no stranger to laughter either. Her psychedelic freakout in "Selma's Choice" (Season 4, Episode 13) is a classic scene (NEVER drink the water at Duff gardens!), as was the time she broke Ralph Wiggum's heart. Ultimately, Lisa will never stop her crusade to try and save the world, become president, bond with her favorite substitute teacher, and call out bad actors. While that might rub some people the wrong way, it'll never stop her from trying.

2. Homer Simpson

Quite possibly more iconic than Mickey Mouse himself, Homer Simpson (Castellaneta) may just be the most famous character in the history of animation. The patriarch of the Simpson family, Homer is an incompetent buffoon — but hey, that's why we love him. He's terrible at his job as safety inspector for Mr. Burns' nuclear power plant, spends every free moment eating donuts, drinking at Moe's and making other questionable decisions (remember the sandwich? Or his pet lobster? Or tripping out at the chili cook-off?). Such memories might not make him seem like a particularly suitable dad (along with his fondness for strangling Bart), but there's just something about Homer that makes it work, and perhaps makes us all see a bit of ourselves in the big dummy.

What makes homer so incredibly lovable is his neverending efforts to make himself and his family better. Though he's quite terrible at it, he's always trying, and that has to count for something. In one of the show's most heartfelt episodes, "One Fish, Two Fish, Blowfish, Blue Fish" (season 2, Episode 11), Homer is preparing for death as he may have ingested a poisonous fish at a Japanese restaurant. It's a beautiful episode that showcases just how much Homer loves his family, and how much he wishes he could have connected better with all of them. 

The ultimate everyman, Homer is also arguably the most quotable characters in television history, here's a mere sampling of his classic lines: 

"I am so smart! I am so smart! S-M-R-T!"

"To alcohol! The cause of, and solution to, all of life's problems."

"If you don't like your job, you don't strike. You just go in every day and do it really half-assed. That's the American way."

"Operator! Give me the number for 911!"


1. Marge Simpson

The woman with hair by Frank Lloyd Wright (according to Apu), there's nobody quite like Marge Simpson (Julie Kavner). Wife to Homer and mother to Lisa, Bart, and Maggie, Marge is often thought of as a simple housewife, but as "The Simpsons" has proven time and again, Marge is more multi-dimensional than just about anyone else on the show. One of her best episodes, the underrated gem "Scenes From the Class Struggle in Springfield" (Season 7, Episode 14), shows Marge's desperation to fit in to elevate herself above her humdrum middle class life, before realizing that the real magic of her life lies in the love of her beautiful family.

Though sometimes the citizens of Springfield get frustrated with Marge — whenever she gets up to speak at town hall meetings, the groans are audible — she's almost always right, such as when she knew the monorail was no good in the phenomenal "Marge vs. The Monorail" (Season 4, Episode 12). While a lot of the humor comes from other characters (though Marge still has plenty of jokes for herself, and "I just think they're neat!" is an all-time quotable line), the heart of the show undeniably runs through the amazing blue-haired matriarch of the Simpsons family, making her the single greatest character in "The Simpsons."