The 20 best ‘Simpsons’ characters
Animated comedies are ten a penny nowadays, but throughout the 1990s and early 2000s, there was only one real champion, and that was undoubtedly The Simpsons. The show first aired in 1989 and quickly established itself as a work of true genius, originating from the brilliant mind of Matt Groening.
Through Groening’s show, we were introduced to some of the most iconic animated characters of all time, including the actual Simpson family, comprised of Homer, Marge, Bart, Lisa and Maggie, and a swathe of supporting stars. Springfield was so populated with true-to-life characters that it often felt like a genuine place.
The true genius of The Simpsons is that it appeals to both young and old. Many of us watched the show after school merely because of the baseline humour and jokes. However, there is a richness to the show that can only be appreciated from an adult perspective, whether it be the risqué moments or the popular culture references.
So from a terrible lawyer to a grumpy bartender via school teachers and children’s entertainers, we’re going to name the ten greatest characters that have ever cropped up in that funny little town of Springfield. Without further ado, let’s get started.
The 20 best characters in The Simpsons:
20. Eleanor Abernathy (Crazy Cat Lady)
What’s an episode of The Simpsons without a feral feline being hurled at the screen? Of course, the woman behind those ferocious balls of fur and claws was none other than Eleanor Abernathy, AKA Crazy Cat Lady.
Having been a lawyer and doctor, Abernathy’s role in The Simpsons has been a routine of appearing in a scene, throwing some cats, causing some chaos, and leaving in a mumbled rage. It is a role she performs with aplomb, providing a moment of comic relief in some of the most serious scenes.
19. Comic Book Guy
One of the most adored comic book shop owners in history, Jeffrey Albertson, better known as Comic Book Guy, is one of the best-loved characters on the show. With his infamous catchphrase “worst (insert noun) ever” etched into the collective consciousness, Comic Book Guy is a Springfield institution.
Having first appeared on the show in ‘Three Men and Comic Book’ and despite having come face to face with his hero Stan Lee, the shop owner long ago left the shackles of the store to enjoy life in outer Springfield, enjoying relationships with both Edn Krabappel and Agnes Skinner.
18. Groundskeeper Willie
The greens of Springfield Elementary would look a lot different without the careful curation of Groundskeeper Willie. A Scottish native, the gruff and red-haired groundskeeper is both warm and frightening at every turn. Delivering rage-filled diatribes that usually revolve around hatred for the other members of the United Kingdom, Willie has proved to be both saviour and sacrificer of the school on numerous occasions, but he is always an admirable foe for Principal Skinner.
While his temper is unmatched on the show, Willie’s ability to lose his cool is also what makes him a hilarious component of most storylines. Famously gliding through a ventilation system like no other (“Grease me up, woman!) Willie is an unsung hero of the show.
17. Jeremy Freedman (Squeaky Voiced Teen)
When men hit puberty, there is nothing their friends enjoy more than when their pre-pubescent voice and their adult voice mix and fight it out mid-sentence. For most, this will happen on only a few occasions in one’s lifetime; however, for Jeremy Freedman, more usually known as the Squeaky Voiced Teen, it is a constant struggle.
This simple yet effective joke is the substance of every Freedman appearance across his many, many job roles, yet, somehow, it rarely gets dull. His duelling vocals only exacerbate his naivety and inexperience, and when put into uncomfortable situations, the joy for the audience is only heightened.
16. Maggie Simpson
While it is easy for us to avoid the majority of The Simpsons’ major players in our list owing to the strength of the shows supporting cast, it is hard to ignore the powerhouse of Maggie Simpson. Silent yet deadly, as Mr Burns and a host of others have found out to their detriment, Maggie is able to convey a range of emotions with her pacifier alone.
As well as developing a healthy rivalry with a mono-browed baby, Maggie has also saved the life of her father, who was also her first word, on numerous occasions and, when the time calls for it, has a habit of developing superhuman strength.
15. Troy McClure
Troy McClure’s filmography sadly primarily consists of cheap infomercials and ridiculous educational films, having once been a Hollywood star of the 1970s before fading into obscurity. Still, we always love when McClure pops up in Springfield with his iconic line, “Hi, I’m Troy McClure. You may remember me from such films as [enter useless instructional DIY home video].”
Ultimately, McClure is a poor actor, which is why he is resigned to starring in such low-budget projects, but he has one of the most memorable voices in The Simpsons, forever burned into our ears, and for that, you can’t help but love him. There’s no role that McClure will turn down, however undignified, and we can’t thank him enough for that.
14. Lionel Hutz
Lionel Hutz is Springfield’s local shyster lawyer, who, despite his unethical practices, somehow continues to find himself with work. His most frequent employers are the Simpson family themselves, often because he is the only lawyer they can afford.
Hutz’s legal office is located in Springfield shopping mall, brilliantly titled ‘I Can’t Believe It’s A Law Firm!’, which also just so happens to offer a shoe repair service. He’s a true “ambulance chasing” lawyer, who is the last person you’d want representing you in court, but we just can’t help but love his foolish and devious ways.
13. Grampa Simpson
There’s a running theme of tragedy running through the characters fortunate enough to find themselves on this list, and Grampa Abe Simpson suffers the true tragedy of old age. The father of Homer and the grandfather of Bart, Lisa and Maggie is known for his senile behaviour and rambling nonsensical stories.
Much of Abe’s biography is revealed through his own telling, although most of it is contradictory in nature, although his stories are always amusing. The brilliance of Grampa Simpson is that he is worthy of our pity, even if he rarely gets it from other characters, and is a stark reminder of what is around the corner for us all.
12. Barney Gumble
If tragedy is the name of the game in terms of the best Simpsons characters, then, in some ways, Barney Gumble subverts it whilst retaining our sympathy. Barney is the Springfield town drunk, although, in many ways, he seems the happiest of the bunch, accepting his lot in life.
However, Barney, once a promising young student, was set to study at MIT before Homer introduced him to beer. The situations that Barney gets himself into are rather unbelievable, but his constant drinking makes him impervious to shame, making him one of the most amusing characters in the show.
11. Ralph Wiggum
What he lacks in traditional intelligence, Ralph Wiggum makes up for in pure love. The son of the Police chief, Ralph is regularly the butt of the joke in the scenes that feature him, but such is his lack of studious skills that he is usually blissfully unaware. It provides the character with a sense of trance-like calm that few possess in Springfield.
First appearing in ‘Simpsons Roasting on an Open Fire’, Ralph has become a much-beloved figure over his years on the show. Having eaten everything from worms to crayons and the Easter Bunny, it is safe to say that few things trouble the genuinely joyful schoolkid, delivering some of his best lines with a serene blankness that Buddhist monks take decades to perfect.
10. Edna Krabappel
The first thing that comes to mind thinking of Edna Krabappel is a form of tragic desperation. Bart’s school teacher was once an optimistic young lady with a passion for helping others, but years in the education system, especially teaching students like Bart, wore her down, and she became largely miserable.
Many Simpsons episodes with Edna at their core, surrounding her ever-searching quest to find love, frequently ending in heartache. There’s a seasons’ long on-off relationship between Edna and her boss Seymour Skinner, but it never quite comes to fruition, and Edna resorts to smoking, drinking heavily and having a rather dour outlook on life.
9. Sideshow Bob
The hilariously named Robert Underdunk Terwilliger Jr. is better known by his stage name Sideshow Bob. He never quite lived up to his genius potential as a graduate of Yale University, where he developed his iconic transatlantic accent, and ended up as a comic assistant on Krusty the Clown’s comedy show.
Following Bart’s prevention of Sideshow Bob getting Krusty imprisoned (after suffering comic abuse on the show for far too long), he vows to take revenge by killing Bart, assuming the role of evil genius throughout the season. However, Sideshow Bob fails miserably, although his efforts provide some of the best moments in the show.
8. Jasper Beardsley
Pensioners have provided some of The Simpsons’ finest moments, and it is hard to deny the hilarious impact of Jasper Beardsley, friend and sometime foe of Abe Simpson. A force to be reckoned with at the Springfield Retirement Castle and known for his paddlin’ abilities, Jasper is rightly regarded as one of the show’s finest characters.
First appearing in ‘Homer’s Odyssey’, Jasper has routinely provided deadpan relief from the chaos of the show. Whether he attempts to avoid the WWII draft by pretending to be a woman or cryogenically freezing himself in the ice cream section of the Kwik-E-Mart, Jasper’s baritone voice is always a welcome moment.
7. Waylon Smithers
In many ways, Smithers is by far a more complex character than his boss and unrequited lover, Mr. Burns. Smithers’ undying devotion to Burns is surprising at times, especially when Burns’ inattention clearly cuts his assistant to the core, and Smithers’ affection for Burns clearly runs deeper than merely fulfilling his career duties.
The relationship between Burns and Smithers is a running joke throughout the series, and a memorable moment comes when Burns tells Smithers he had a dream about Marge flying in through his window, only for Smithers to imagine that very same dream but with Burns falling into his arms. Again, as with all the very best Simpsons characters, Smithers is the essence of genuine tragedy.
6. Hans Moleman
Few characters are as impactful as Hans Moleman. Rarely a scene featuring the poorly-sighted pensioner goes by without a tragically funny and unfortunate occurrence happening to him. Making his first appearance in ‘Scary Movie’ as a silent movie-goer in Tracy Ullman’s short, Moleman is now a clear fan-favourite.
Unlike most of the characters in The Simpsons, Moleman is often killed off in his appearances, and he experienced 42 on-screen deaths, including being eaten by both wolves and alligators, being hit by numerous cars, being trampled by a dinosaur and a whole host more. Each death proves to be funnier than the last.
5. Krusty the Clown
How could a Jewish, alcoholic, chain-smoking children’s entertainer not sneak his way into the top five best characters? Krusty epitomises the misery caused by years in show business but with no other avenue down which to turn. He’s cynical to the point of hilarity and utterly negligent as to whether children actually enjoy his entertainment or his branded wares are safe for use.
Underneath the makeup, Krusty looks startingly like Homer Simpson and uses his entertainer’s disguise to cover up his inner sadness. Despite his cynicism, Krusty never fails to put on a smile when it’s time to shine and perform his ridiculous laugh. And who could forget his heartbreaking rendition of ‘Send in the Clowns’?
4. Seymour Skinner
The victim of his overbearing mother and his cruel-hearted boss Superintendent Chalmers, Seymour Skinner is the principal of Springfield Elementary School. A complete lack of resources and several unruly students, including, of course, Bart Simpson, has most of Skinner’s episodes feature him in a constant state of stress.
Skinner once served in the Green Berets in the Vietnam War, explaining his military approach to discipline. He’s perceived as Bart’s antagonist, and vice versa, but the two actually develop a level of respect for one another. An on-off relationship with teacher Edna Skinner is also a great source of hilarity.
3. Milhouse Van Houten
Considered perhaps the ultimate sidekick to the naughty by-nature Bart Simpson, Milhouse arrived in Springfield in the episode ‘Simpsons Roasting on an Open Fire’ and has won our hearts ever since. A perennial sap, what Milhouse lacks in charisma, he makes up for with clownish one-liners. We’re not talking about Krusty here; more like the sad clowns you see in old black-and-white movies. The juxtaposition of this despair with his occasional wins makes Milhouse such an endearing force on the show.
The son of Kirk and Luanne Van Houten, Bart regularly takes advantage of Milhouse and is usually the butt of his jokes. While it can have a habit of forming a sense of sympathy for the beleaguered ten-year-old, the character has been a part of some of the show’s most iconic moments. Few can forget his near-perfect line, “Everything’s coming up, Milhouse!”
For this line alone, he deserves to be included on the list of our favourite characters from The Simpsons.
2. Homer Simpson
The temptation with this list was to leave the entire Simpson family out of it, a testament to the many excellent characters Matt Groening has devised. However, it’s just hard to look beyond Homer; he’s simultaneously lovable and reprehensible and is the primary catalyst behind much of the show’s best moments.
Homer is the living embodiment of the once-stereotypical working-class American. He’s lazy, overweight, daft, and loves beer and junk food, and yet he is rather brilliant. He’s provided truly memorable scenes throughout his onscreen life and is a true icon of animated comedy. Quite simply, Homer Simpson is The Simpsons.
1. Moe Syzslak
However, Homer is not our number one choice. Instead, we’ve given the top spot to a man on whom Homer relies oh so much, the owner of his favourite drinking hole Moe Syzlak. Moe is tragedy personified; he’s lonely and miserable and suffers some of the worst luck known to man. The result is a sometimes cruel man with little patience.
However, beneath that exterior lies a man who is tender and kind and who just wants to be loved. Moe believes he is ugly in appearance, but a brilliant episode in which he gets plastic surgery shows that beauty is indeed only skin deep and that the true value of someone lies further inside them.
Moe’s provided some of the funniest moments on The Simpsons, whether naively answering Bart’s prank calls or declaring his love for Marge. Moe is simply the best character in The Simpsons by some stretch, we’d say.
