For 30 years now, The Simpsons have entertained countless television viewers of multiple generations from a plethora of countries. The central family of Homer, Marge, Bart, Lisa and Maggie are one of the most iconic television families of all-time, but in the series itself they are simply the five leads, backed by an enormous cast of supporting characters. Countless supporting characters have been featured in the series over its run of 650+ episodes, many of whom have taken centre-stage in multiple episodes. However, in a cast of hundreds there are going to be some that stand out from the crowd, whether because of their personalities, their significance to the titular family or the focus that they have had over the years. So, to mark 30 years of The Simpsons, here are the 30 best supporting characters.
30. Troy McClure
Professional actor Troy McClure popped up regularly from Seasons 2-10, voiced by regular guest star Phil Hartman. A washed-up B-Movie star, Troy primarily appeared as the host of educational films and television game shows, the scripts often being a great send-up of those dreadful educational films that you are forced to watch as a young school pupil, and to these Hartman brought a really cheesy charm to his voice performance. If only he had voiced the real things. The character was retired following Hartman’s murder in 1998, but his legacy endures – over 20 years after his final appearance, countless fans continue to think back warmly to those iconic introductions of “Hi! I’m Troy McClure! You may remember me from such films as…”
29. Hans Moleman
Some of the most iconic cartoon characters in history are ones who survive against impossible odds – just look at Wile E. Coyote. While Hans Moleman is by no means one of the more iconic Simpsons characters, he has been at the centre of a running gag (especially in the earlier seasons) which saw the small old man return from deadly experiences, just like that Coyote. These include vehicle explosions, being set on fire, getting crushed, being run over, a trip to the electric chair and being drilled in the brain by a delirious Mr. Burns.
Moleman has experienced bad luck to the extreme and, while his appearances are not that frequent, they have been the source of great slapstick and some quite surreal moments, making him a memorable addition to the series. And let’s not forget his daft, yet hilarious, short film – Man Getting Hit by Football.
28. Snake Jailbird
Snake is Springfield’s career petty criminal, his usual crimes involving theft (for which he is often armed), and yet he never seems to stay in jail for very long. Heck, the number of times that he has been in and out of jail, you have to wonder whether Springfield’s prisons have revolving doors. Ultimately, Snake (nicknamed after the large serpent tattoo on his arm) simply hates society and speaks his mind unashamedly over it.
With a tough guy image and a surfer dude accent, which makes the delivery of his more sincere lines all the more amusing, Snake may not be a successful criminal, but he is nevertheless a loveable character who oozes cool, while his confrontations with characters such as Homer and Chief Wiggum have been the source of some terrific slapstick gags. He is one premium dude indeed.
27. Kearney Zzyzwicz
Kearney is rarely seen without his best friends Dolph and Jimbo, and Bart describes them in Season 1 as “the toughest kids in school”, which they have proven time and again by beating up other kids, showing no regard for authority and regularly shoplifting. Kearney certainly fits the tough-guy type with his shaven head, stocky build and angry expression, which make his desire to learn history in Season 4 and his place on the church council in Season 13 all the more amusing.
Kearney has been fleshed out far more than Dolph or Jimbo though, with his obscure age being a running gag in the series, as he remembers Watergate, has been to prison, had an affair with Jimbo’s mother and goes to the same school as his son from a previous marriage. The answer ultimately is that he has been held back a year by the school so often that he is now almost 30 and fed up with an educational establishment that does not know how to teach him. If that does not testify to the quality (or lack thereof) of Springfield Elementary, then what does?
26. Fat Tony
Serving as the Springfield Mafia’s boss from Seasons 3-22, Fat Tony’s appearances were very few in number compared to many other characters on this list, but they were very memorable. Voiced with sinister charm by regular guest star Joe Mantegna, Fat Tony was a terrific send-up of the classic cinema mobster – he was an intimidating figure whom you cannot help but root for, conducting his underground crime at the Legitimate Businessman’s Social Club, and regularly using bribery to get out of trouble.
While he may have been quite sinister, that made his softer and more human side all the more amusing – he doted on his son Michael and liked Garfield because the fictional cat hates Mondays. Fat Tony died from a heart attack in Season 22, and his cousin Fit Tony (also voiced by Mantegna) replaced him as the town’s Mafia boss. Fit Tony, however, subsequently gained a lot of weight and changed his name accordingly, emphasising that it is impossible to imagine anyone other than Fat Tony running Springfield’s underground crime scene.
25. Agnes Skinner
Permanently frowning and forever short-tempered, Agnes is Principal Skinner’s mother. A crotchety old lady, Agnes is a very well-written embodiment of those old ladies who have reached a point in life where they will uncaringly say whatever they like – they are rude, they are sharp-tongued, but you cannot help but respect and appreciate them for being so forthright and unconcerned with the opinion of others.
Agnes’s scenes with Principal Skinner are her best though – barking “Seymour”, she never fails to put him in his place and leave him terrified (an ability that she once utilised to also put Edna Krabappel, Jasper and the entire Simpson family in their place at once), and is more than happy to embarrass him in front of his students. She represents what nobody really wants their mother to become in her elder years, but does so in such a hilarious manner that you can imagine yourself being okay with having such a mother.
24. Martin Prince
It would be fair to say that we all knew a Martin Prince when we were in school, or maybe even displayed similar traits to Martin as 10-year-olds. Martin is the teacher’s pet in Bart’s class, a highly academic A-grade student whose social skills are somewhat lacking – he seems oblivious to the fact that what he considers cool or interesting are not considered so by any of his classmates. Heck, for Bart’s birthday in Season 3, he gave Bart a blazer and flat cap matching his own so that they could “be twins”.
Because of this, he is a frequent target for the school bullies and manages to frustrate his teachers. Nevertheless, Martin is a good-natured and well-meaning person who makes the dynamic amongst Springfield Elementary’s fourth graders an interesting one – he is overly friendly to all of them, none of whom really want to hang out with him, but they remain polite enough to attend his birthday party in Season 8, and even school bully Nelson has stood up for him on occasion.
22/23. Lenny and Carl
Having been friends with Homer since their youth, Lenny Leonard and Carl Carlson are now his fellow Sector 7G workers at the Nuclear Power Plant and barflies at Moe’s Tavern. A long-serving double-act, who regularly serve as voices of reason and comedic foils to Homer, the two are very rarely seen apart. While intelligent (they each hold a Master’s degree in Nuclear Physics), they are at times juvenile – best exemplified when they called themselves “Poo” and “Ass” during a bowling game in Season 11 – but are kind-hearted and love Homer, although not quite as much as they love each other, with a running gag being hints that they may be more than just friends. As such, Lenny and Carl are dependable characters who have become staples of the Power Plant and Moe’s Tavern scenes, a big part of the lives of the Simpson family and two of Mr. Burns’s more favoured employees.
21. Dr. Nick
Although his full title may be Dr. Nick Riviera, his surname tends to be forgotten, as most scenes that he appears in start with him jovially going “Hi, everybody!”, followed by a warm response of “Hi, Dr. Nick!”. A highly inept member of the medical profession who tries to increase his number of patients by advertising himself to be “just as good as Dr. Hibbert”, Dr. Nick is of Hispanic origin, the language-barrier which that causes having been the subject of several gags.
His ineptitude has been the source of some of the series’ more absurd moments, such as when he performs heart surgery on Homer while singing to himself “The knee bone’s connected to the something…”, and a visually absurd moment where he was confronted by a patient who now had an arm where a leg should be and a leg where an arm should be. You definitely would not want this man tending to your medical needs, but Dr. Nick brings an irresistible energy to every scene that he is in, and as such has become quite an endearing character.
20. Groundskeeper Willie
Ah, The Simpsons, a series in which immigrant characters are almost always stereotypes, and Groundskeeper Willie is no exception. He has a thick Scottish accent, a red beard, a short temper, an argumentative nature, takes regular swigs from a hip flask of whisky, and goes commando whenever he wears a kilt, all of which have been the source of hilarious gags over the years. Willie takes great pride in the school site which he maintains and has an interesting dynamic with the students (many of them love trying to play pranks on him, but they all ultimately fear him), while he is unafraid to speak his mind, the one character who can put him in his place being Skinner, with whom he has a real love-hate relationship.
Willie’s uncaring attitude to what he says, however, has been best displayed in some terrific insults, which include “bloated gasbag”, “croquet-playin’ mint-muncher”, “blouse-wearing poodle-walker” and the time that he referred to the entire French nation as “cheese-eating surrender monkeys.”
19. Dr. Hibbert
Springfield’s most prominent and competent doctor, Julius Hibbert is among the more dependable supporting characters of the series’ run. While he is not a character who takes centre-stage, Hibbert’s scenes usually boast good comedy value thanks to their sharp wit and the character’s force of personality, which has elements of Dr. Cliff Huxtable from The Cosby Show. Hibbert is a very warm and jovial man, who has an iconic and surprisingly infectious laugh that he implements a lot, even at quite inappropriate moments, bringing a degree of humour to some of the more serious moments in which he delivers bad news.
His sense of warmth comes through most when he is treating the Simpsons kids (during a flashback in the Season 4 episode Lisa’s First Word, he doted on the infant Lisa and happily gave her a “wowwipop”), although that did not stop him from taking a defibrillator to Bart’s coccyx once in Season 11 as it was “good for the batteries”. As such, Dr. Hibbert is a very endearing character, boasting great qualities to look for in a member of the medical practice.
18. Krusty the Clown
Krusty the Clown is (at a surface-level) an understandable character to younger viewers, most of whom would no doubt have experienced those incredibly energetic children’s entertainers at some point, but (on a deeper level) is understandable to adult viewers as he is a human character who endures real struggles. Scenes where Krusty is at work boast real energy and some terrific slapstick gags, but that is a totally different Krusty to the one who is not working.
While his cynical comments are often quite amusing, Krusty’s humanity is seen in his battles with addiction and depression, the cause for which ultimately stem from the more devastating moments of his youth. As such, Krusty is a multi-layered and quite complex character, whom many viewers will either sympathise or empathise with, while his struggles with addiction and depression feel especially relevant today, in an era where people are all too aware that being a successful celebrity (and a comedic one at that) does not make you immune to mental health struggles.
17. Mayor Quimby
Nicknamed “Diamond Joe”, Mayor Quimby is a stereotypical member of the Democratic Party and a parody of the various Kennedy family members who entered into the world of politics. The latter is found in clever little details, such as his various middle names including Fitzgerald and Fitzpatrick, his serial womanising and a voice reminiscent of the late President Kennedy’s. As a politician, Quimby is highly self-serving and very corrupt, often taking bribes, bribing Chief Wiggum (with whom he regularly engages in very amusing power struggles) and even embezzling tax money, with a hilarious detail in his office being the town seal on the wall – motto, “Corruptus in Extremis.”
Quimby regularly tries to get himself out of hot water with insincere public apologies, but he is at his most amusing when he is confronted by the citizens of Springfield and tries with absurd brilliance to blag his way out of the situation, which has regularly served as the catalyst for a single episode’s self-contained storyline.
16. Chief Wiggum
The obese and dim-witted head of the Springfield Police Department, Chief Wiggum is an extreme stereotype of a lazy cop. Wiggum’s attitude to law enforcement is generally naive and laid back, and hilariously so, with the Chief often found sat at his desk, munching his way through a box of doughnuts, dismissing the concerns of the townsfolk and leaving it to Officers Eddie and Lou to do the hard work. Furthermore, Wiggum is corrupt, often taking bribes from Mayor Quimby, with whom he engages in bitter and highly entertaining power struggles.
Despite this, Wiggum is not all that bad and quite a well-rounded character. He loves his job and, when he briefly loses it in the Season 8 episode Homer vs. the Eighteenth Amendment, he feels lost and directionless. Furthermore, Wiggum adores his 8-year-old son Ralph, whom he would do literally anything for – heck, how many other fathers would eat a crayon sandwich to avoid hurting their child’s feelings?
15. Sideshow Bob
Sideshow Bob’s appearances in the series are comparatively few next to most of the characters on this list. However, when his appearances do come, they are always amongst the highlights of the season, and the character has gone on to become a fan-favourite. With the focus of the character being his desire to kill Bart, following the boy’s frequent foiling of his illegal schemes, Sideshow Bob has become a great source of drama, as viewers are often left wondering what he is plotting and how he will execute his scheme, and also a great source of physical comedy.
His appearance itself is highly comical (springy hair and oversized feet, which themselves have provided great slapstick), but one of the most memorable slapstick sequences of the entire show is a hilariously absurd scene that sees a dishevelled Bob trying unsuccessfully to navigate a field of rakes. However, the most memorable aspect of the character is Kelsey Grammer’s outstanding voice performance, the Cheers and Frasier star bringing a terrific sense of theatricality and a sinister edge to the character with his distinctive smooth, baritone voice.
14. Comic Book Guy
Proprietor of The Android’s Dungeon and Baseball Card Shop, Jeff Albertson will forever be better known as Comic Book Guy, his real name never revealed until Season 16. Comic Book Guy really could be a character from The Big Bang Theory – he is very intelligent, with an IQ of 170, but has no social skills, instead being a “45-year-old virgin who still lives with his parents”, and one who is obsessed with all things science-fiction and fantasy, boasting an enormous collection of merchandise and an in-depth knowledge of all things Star Wars, Star Trek and superheroes.
His lack of social skills is seen in his surly and sarcastic attitude, which has been the source of some terrific gags over the years as he speaks his mind in a highly amusing fashion, happily putting the kids of Springfield that frequent his premises in their place, and even casually breaking the fourth wall in the Season 11 episode Saddlesore Galactica. However, Comic Book Guy is best known for his catchphrase “Worst [insert noun] ever”, often saying exactly what the audience is thinking.
13. Apu Nahasapeemapetilon
As manager of the Springfield Kwik-E-Mart, Apu was introduced in Season 1, serving as a terrific satirisation of the changing face of American convenience stores, and also one of the series’ most prominent stereotypes. An Indian immigrant who keeps a small statue of Vishnu on display, Apu is incredibly hardworking and very friendly, always saying to customers “Thank you, come again!” even when they have angered him. He is also highly intelligent and a very talented singer.
However, he regularly makes veiled insults about America, cons his customers with inflated prices, and sells food that is nothing short of a health hazard, which was the catalyst for the brilliant Season 5 episode Homer and Apu. While latter seasons saw him become more bitter and cynical after he and his wife, Manjula, have octuplets in Season 11, and the character has gone on to become quite a controversial figure, in the first decade of the series’ run he became one of the most memorable supporting characters, bringing real energy to every scene he was in, and could always be depended upon as a great source of humour.
12. Nelson Muntz
While Kearney, Dolph and Jimbo are Springfield Elementary’s longest-serving bullies, Nelson’s the one who gets the most focus (and regularly joins the older three in their antics). A long-serving frenemy of Bart’s, Nelson is a fellow fourth grader who has beaten up just about every kid in school on multiple occasions, especially Martin Prince and Milhouse Van Houten, and has teased just about everyone as well, with his signature “ha ha!”. He is dim-witted though, as shown when Lisa shot down one of his insults with a logical argument, causing an uneasy Nelson to jump off the school bus.
While a dim-witted bully on the outside, however, there is more to him than meets the eye, as he loves fresh huckleberries, taking joy in telling others about them, and is a huge Andy Williams fan. However, Nelson is also the most well-rounded of all the bullies in Springfield Elementary as he comes from a broken home, his father having abandoned him, while his neglectful mother is an alcoholic prostitute. As such, Nelson’s penchant for bullying and lashing out is a manifestation of his deep-rooted insecurities, while the tough guy image that he so values hides a sensitive soul with a heartbreaking past.
11. Selma Bouvier
Along with her twin Patty (who she is very rarely seen without), Selma is one of Homer’s cynical, chain-smoking sisters-in-law and long-term enemies, having always disliked him and thought him unworthy of Marge’s love. Despite being the series’ longest-serving double-act, Selma is the Bouvier sister who makes it on to this list as she has had far more character development and focus than Patty.
Unlike Patty, it is strongly implied that Selma has an underlying (and very begrudging) respect for Homer, notably in Season 4 when she expressed admiration for his ability to cope with three children and envy that he has a family. And that is what makes Selma the well-rounded Bouvier twin – her vulnerability. Her various marriages have provided us with some great episodes, but they ultimately reflect that she feels an overwhelming need to be loved, as well as a heartfelt yearning to start a family herself. The real testimony to how well this has been realised and developed over the years came when she adopted baby Ling in Season 16, in heartwarming scenes which left the viewer feeling a sense of joy for Selma.
10. Principal Skinner
Having been Principal of Springfield Elementary for many years, Seymour Skinner has been a prominent supporting character since Season 1. While he is proud to have a child as gifted as Lisa at his school (though he continues to underestimate her due to his somewhat short sighted and naive nature), he is regularly found at loggerheads with Bart, and is often the victim of the young troublemaker’s pranks. A veteran of the Vietnam War, Skinner regularly tries to no avail to implement his military training in both his home and work lives, which makes it all the more hilarious when he is left terrified by his boss Superintendent Chalmers and his mother Agnes.
Skinner’s dynamic with Bart was cemented as one of the best in the series in the 100th episode (Sweet Seymour Skinner’s Baadasssss Song), when the two had a short-lived friendship which established that they value each other as enemies, and they have resultantly been frenemies ever since. Add into the mix Skinner’s on-off romance with Edna Krabappel from Seasons 8-15, and you have a very well-rounded and important supporting character that countless fans were invested in by Season 9, hence why even Matt Groening does not like to be reminded of the Season 9 episode The Principal and the Pauper. That episode saw Skinner revealed to be an impostor named ‘Armin Tamzarian’, a revelation which the town brushed under the carpet under the threat of penalty of torture, reflecting that nobody could imagine a different Principal Skinner.
9. Moe Szyslak
Owner of Moe’s Tavern, the curmudgeonly bartender has served as the enabler for Homer, Barney, Lenny and Carl’s heavy drinking since the first episode, and is the victim of Bart’s hilarious prank calls. Despite his curmudgeonly attitude and near-permanent frown, there is far more to Moe than meets the eye. He dearly loves and values Homer, Barney and the others as friends rather than just customers (that being said, he would still love Barney to pay off his bar tab at some point), as established in the first episode when he tries to cheer up a forlorn Homer in a moment of sincere compassion. T
his love for his friends and willingness to help people in need is what makes Moe so endearing, despite his regular angry outbursts. As the series has progressed, he has become a more rounded character. On a surface-level, Moe’s flirtatious behaviour towards Marge can be seen as a send-up of those who develop romantic feelings for their best friend’s spouse, but ultimately it reflect his deep-rooted desperation for love and companionship. Moe also struggles with depression and has attempted suicide a number of times, but the fact that Homer and the others have stopped him from doing so testifies to the fact that he is a much-loved and dependable character, and that the series cannot be imagined without him.
8. Waylon Smithers
As personal assistant to Mr. Burns (who is utterly dependent on him) and part of the Springfield Nuclear Power Plant’s executive board, Smithers was initially depicted as a supporting antagonist, often acting as Burns’s henchman and partner-in-crime (sometimes against his better judgement), and unafraid to lord his power over the Plant’s blue-collar workers. Smithers has been depicted as the consummate professional – meticulous in both his appearance and his approach to all 2,800 duties of his job. However, Smithers has also been the subject of one of the series’ longest-running gags – his closeted homosexuality.
Starting with the Season 1 episode The Telltale Head, and ending when he came out in the Season 27 episode The Burns Cage, the references to this were initially subtle hints that he was smitten with Burns, but becoming more overt hints that he is a closeted homosexual as the series progressed. The latter included his obsession with Malibu Stacy dolls, his interest in the song ‘It’s Raining Men’, his vacationing on an all-male island resort and his insistence that he only visited the Springfield Burlesque House because his parents forced him to. While these moments boast clever screenwriting and some hilarious gags, they ultimately reflect the fact that there is more to Smithers than meets the eye, that ultimately he struggles with insecurity and yearns for companionship, which make him a much more rounded and much more relatable character.
7. Barney Gumble
Homer’s lifelong best friend, and Moe’s best customer, Barney Gumble is a slovenly alcoholic who can almost always be found sat at the bar in a state of inebriation. Similarly to Homer, Barney’s drunkenness has been a great source of humour, particularly in the earlier seasons, with great verbal gags stemming from his interactions with other characters, perspective of the world around him and casual attitude towards his unkempt appearance, and also some terrific slapstick as he takes some tumbles and gets into bar brawls. Barney is more than just a joke character, however, rather he is very well-rounded – good-natured, fiercely loyal to his friends and actually quite a tragic figure.
His backstory reveals that he was once a studious high-schooler with academic ambitions but, after Homer gave him his first beer, he became hooked on alcohol, which led to him never pursuing his abilities. When Barney went sober for the first time in Season 5 he almost became an astronaut, and when he went sober in Season 11 he learnt how to fly a helicopter. Furthermore, Barney is a wonderful singer, who could easily have tried for a solo career after barbershop quartet The Be-Sharps disbanded, but (most heartbreaking of all) he is all too aware of the effects of his alcoholism and made a poignant short film about it in the Season 6 episode A Star is Burns. Altogether, he is one of the most well-rounded and interesting characters in the series, and his prominence in the first 10 seasons has made him one of the most instantly recognisable as well.
6. Edna Krabappel
A prominent supporting character voiced brilliantly by the late Marcia Wallace from Seasons 1-25, Mrs. Krabappel – or Edna, as she became more commonly known – was Bart’s fourth grade teacher at Springfield Elementary, and with him she shared one of the series’ best dynamics. While Bart’s behaviour regularly infuriated Edna, she genuinely cared for him and took pity on him when he felt down. In turn, Bart was (secretly) very fond of Edna, showing compassion when a man broke her heart, and respected her for persisting in teaching him for so long. This dynamic contrasted brilliantly with Edna’s more prominent characteristics.
An extreme stereotype of the jaded teacher who is sick of the educational system, Edna was typically cynical, sarcastic and fed up with her job, which caused her to smoke and drink heavily, but on occasion she showed real warmth to her class. A running gag during Seasons 1-8 was her promiscuous behaviour outside of school, which led to some amusing duologues with the men of Springfield, but ultimately reflected that Edna was desperate for true love after her husband left her prior to Season 1. Her on-off romance with Principal Skinner from Seasons 8-15 added a fun new dynamic to the series and got fans even more invested in Edna. She ultimately found her true happiness when she married Ned Flanders in Season 23, and flourished as both Ned’s wife and the stepmother of Rod and Todd. Following Marcia Wallace’s death in 2013, Edna died off-screen and has been regularly referred to since. Gone but never forgotten, Edna was a fantastic addition to the series, which has not been the same without her.
5. Milhouse Van Houten
As Bart Simpson’s long-suffering best friend, Milhouse is one of the most prominent child characters in the series, and also one of the most bullied. Milhouse is very naive, which Bart often takes advantage of, and is also regarded as a ‘poindexter’, making him a frequent target for school bullies Nelson, Kearney, Dolph and Jimbo. However, Kearney and Nelson showed him real compassion when his parents (Kirk and Luann) split up, as they too came from broken homes. Kirk and Luann’s divorce was the catalyst for many Milhouse-focused moments of character drama, as it hit him hard in a way that no punch from Nelson ever could, ultimately making him a more rounded character.
Despite being at the centre of some serious self-contained storylines and ongoing subplots, Milhouse has been very prominent in some hilarious scenes over the years. He and Bart deeply care for each other, despite clashing at times, and get up to all sorts of mischief, which has been the source of some terrific slapstick gags and a highly entertaining dynamic. Furthermore, Milhouse’s unrequited crush on Lisa has been the source of some very amusing moments, such as when Lisa let him down gently once by saying that she thought of him more as “a big sister”. As such, Milhouse has become a staple of the school scenes, and also frequently appears outside of school, making him one of the most dependable, recognisable characters of the series, whose fans are delighted whenever “Everything’s coming up Milhouse!”
4. Ralph Wiggum
Son of Chief Wiggum, Ralph is one of Lisa’s fellow second-graders at Springfield Elementary, and has been one of the most prominent supporting characters since the Season 4 episode I Love Lisa, which established Ralph as one of the most complex and multi-layered characters in the series. He is the class oddball, an imaginative, quirky, yet highly unintelligent child, who is mocked by his classmates and belittled by Miss Hoover. Yet he is shown to have hidden depths, being a real gentleman and a phenomenal actor, whose performance as George Washington in the school play was enough to convince school bullies Kearney, Dolph, and Jimbo to read up on their history.
What makes Ralph such a wonderful character is the fact that he is such a genuine person, who is consistently kind-hearted, sincere, and innocent, characteristics that most other Simpsons characters lack. His innocence and ignorance have also made him one of the most memorable characters of the series, as they are the root of his being one of the most hilarious and quotable characters of the series. Ralph’s terrific quotes are too numerous to count, but they include “Me fail English? That’s unpossible”, “My cat’s breath smells like cat food”, “My imaginary friend thinks you’re stupid”, and “Principal Skinner is an old man who lives at the school”.
3. Grampa Simpson
Homer’s father and a World War II veteran, Grampa Simpson is the ultimate satirisation of the older generation within the series – he lives in an old folks’ home, and is very grouchy, highly opinionated, rather out of touch with the world around him and definitely starting to go senile. However, Grampa is easily one of the most hilarious supporting characters. Despite his physical frailty, Grampa is quite energetic, is never afraid to put people in their place with an insult (“What’re you cackling at, fatty? Too much pie, that’s your problem!”), and he is also as sharp as they come. This was best exemplified in the Season 2 episode The War of the Simpsons, when he pretends to cry, which guilt-trips Bart and Lisa into cleaning the house from top to bottom.
Grampa’s early stages of senility are depicted hilariously in his terrific tall-tales – he once claimed to have invented the “turlet”, a story which “begins in 19-dickety-two. We had to say ‘dickety’ cause that Kaiser had stolen our word ‘twenty’. I chased that rascal to get it back, but gave up after dickety-six miles.” Despite his faults, Grampa is a great character who adores his family (even if he tries to avoid showing such feelings to Homer) and his scenes are often full of real warmth, making him a beloved and well-rounded supporting character whom it is hard to imagine the series without.
2. Mr. Burns
Owner of the Springfield Nuclear Power Plant and various other business assets, 104-year-old billionaire Monty Burns has served as the series’ primary antagonist since Season 1, and serves as a parody of various American business tycoons, including the Rockefellers and Fox founder Barry Diller. The former is best seen in the fact that Burns is (in Matt Groening’s words) “the embodiment of corporate greed”, the latter in Burns’s large nose and bald head.
With a near-permanent frown, a threatening voice and no qualms about using his money to his benefit and the detriment of others, he can easily leave even the seemingly braver members of his staff quivering in their boots. His antagonistic actions on a more general level have been best exemplified in his appalling lack of concern for his employees’ wellbeing and the damage that the Power Plant has caused to the town, his unleashing his hounds on visitors he dislikes, and his tight-fisted attitude towards money (although he does resort to bribery out of self-interest). However, Burns has personally inflicted misery upon many individuals, his antagonistic acts towards the Simpson family including sexually harassing Marge, trying to murder Bart and Grampa, exploiting Lisa for financial gain, publicly humiliating Homer, and stealing Santa’s Little Helper’s puppies.
Despite all of this, Burns is also quite a comical character. He has been shown to have quite a sharp sense of wit and has served as a satirisation of businessmen entering (quite corruptly) into the world of politics (he is one of a small number of wealthy Springfield residents to be part of the Republican Party, and ran for State Governor in Season 2). Furthermore, he has been the subject of ingenious references to other fictional business tycoons and/or antagonists such as Charles Foster Kane, Darth Vader, and Hannibal Lecter, while his absurd schemes to remain alive served as the catalyst for the terrific crossover episode with The X-Files – The Springfield Files.
Burns’s physical frailty has also been the source of a simple, yet highly amusing running gag for decades, while his outdated references (which have been increasingly frequent since Season 7) have served as quite a witty send-up of the older generation’s relationship with the world around them. Burns has also been shown to have a more human side as well, as he longs for companionship, feels a number of regrets over his past, and has begrudgingly accepted that money will never give him true fulfilment. Furthermore, his relationship with Waylon Smithers goes far beyond being dependent on him, as he has been shown on numerous occasions to care deeply for Smithers, deep down viewing his assistant as family. As such, Burns is not only the most well-rounded antagonist of the series, but he is one of the most well-rounded, significant and iconic supporting characters of the series.
1. Ned Flanders
Having first appeared in the pilot back in December 1989, Ned is the patriarch of the Flanders family, who live next door to the Simpsons, and has been one of the series’ most prominent supporting cast members since Season 1. Many of his earlier appearances focused on his dynamic with Homer, which Season 3 episode When Flanders Failed cemented as one in which Ned sincerely loves and values Homer, while Homer feels the same way about Ned (albeit much more begrudgingly and secretively), and that the two will always be there for each other when the need arises.
That episode also properly established Ned as a pillar of the community type figure, a role in which he has been overly sincere, generous and, frankly, a do-gooder. Since then, however, he has become more of a satirisation of religious zealots than of overly impressive white picket fence neighbours. However, he has still been fleshed out and focused on far more than most other Simpsons characters. The Season 8 episode Hurricane Neddy gave Ned a much-needed backstory, which establishes that the reason why he is such a sincere, overly cheerful do-gooder stems from his childhood, when his aggressive and volatile nature was spanked out of him (a little too effectively) by therapist Dr. Foster.
Ned has also occasionally been depicted as suffering from deep-rooted insecurity, which is best remembered as being the catalyst for the events of the Season 10 episode Viva Ned Flanders, in which he questioned whether he had really lived. Furthermore, Ned has been central to some of the series’ most tragic moments. He was left broken and grief-stricken when his wife Maude was killed in an accident in Season 11, an incident which impacted him for years to come, that impact serving as the catalyst for a number of future episodes and ultimately being why he became even more protective of his sons Rod and Todd.
While he would later find happiness again in Season 23 when he married Edna Krabappel, that would be short-lived as Edna died off-screen in Season 25. Nevertheless, Ned remains to this day an upbeat and dependable character, a voice of reason to Homer and many other Springfield residents. As such, Ned is the best of all of the supporting Simpsons characters because he has been at the centre of storylines both hilarious and tragic, and is a multi-layered character with a good backstory and well-realised dynamics with so, so many other characters from the course of the series’ run.
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