The 25 Most Underrated "Simpsons" Characters
The best of Springfield's forgotten citizens.
Image via Complex Original
By now, anyone with a functioning pair of eyes has seen an episode of The Simpsons. Since the show's Fox debut in 1989, Homer, Bart, Marge, Lisa and Maggie have become more than pop culture icons, and fully entered the fabric of American life. This has been possible because the writers and producers have gone to great lengths to turn Springfield into a living, breathing town that exists beyond the main cast of characters.
Over the years, side characters like Burns, Ned Flanders, Smithers, Principle Skinner, Apu, and Moe have become cult favorites among fans across the globe. But longtime Simpsons aficionados know that there's a whole world of hilarity outside of even those regulars. That’s exactly why we’re taking a look at the characters from The Simpsons who tend to get overlooked in favor of their more popular contemporaries. From brilliant one-shots to semi-regulars who just haven’t gotten their due, we give you The 25 Most Underrated Simpsons Characters.
25. Dr. Colossus
First appearance: “Who Shot Mr. Burns? (Part 2)” (Season 7, Episode 1)
Voiced by: Hank Azaria
Dr. Colossus only has one conversation throughout the 24 years that The Simpsons has been on the air, but it’s so absurd and hilarious that there's no way he you could make this list without including him. In “Who Shot Mr. Burns? (Part 2),” Colossus appears briefly in a prison cell at the Springfield Police Station, where he mocks Mr. Burns’ plan to block out the sun. With the operatic boasting of a comic book villain, he screams from his cell, “Bah! He is a rank amateur compared to Dr. Colossus!”
He then hits the secret button on his extending “Colosso-Boots,” which causes him to slam his head on the ceiling of his prison cell. It’s a short and brilliant scene, but it instantly makes us wish for a spin-off featuring Colossus fumbling around his devious hideout at Death Mountain.
24. Don Brodka
First appearance: “Marge Be Not Proud” (Season 7, Episode 11)
Voiced by: Lawrence Tierney
His stint may be short, but Don Brodka—“That’s right, Don Brodka”—still ranks as one of the show’s best one-off characters. Voiced by the brilliant, but notoriously difficult to work with Lawrence Tierney, Brodka is the security guard at the local Try-N-Save department store who catches Bart stealing a copy of the video game, Bonestorm.
Tierney provides the gravely voice and salty personality necessary for a former Marine, but it’s his delivery of some of the episode's more subtle jokes, such as the bizarre conversation with the Simpson's answering machine, that elevates Brodka to cult classic status.
23. The Very Tall Man
First appearance: “22 Short Films About Springfield” (Season 7, Episode 21)
Voiced by: Hank Azaria
It's amazing that The Simpsons can create a character for the sole purpose of a single joke and have him become the standout part of one of the show’s best episodes. The Very Tall Man's introduced in “22 Short Films About Springfield” where he humiliates local bully Nelson Muntz, who previously “haw-hawed” about the Tall Man's immense size as he drove by in his shoebox car. His lumbering frame and baritone voice are perfect for this bit part, and though he's only appeared a handful of times since, he’ll always be remembered as a stellar addition to the show’s expansive background of characters.
22. Arthur Crandall & Gabbo
First appearance: “Krusty Gets Kancelled” (Season 4, Episode 22)
Voiced by: Hank Azaria (Crandall) and Dan Castellaneta (Gabbo)
For years, Krusty the Clown was the only act in town. Despite being a vulgar, illiterate alcoholic, he had a legion of fans across Springfield and was filthy rich because of it. But as his act started to wear thin, he was challenged by a rival kid’s TV show host who won the hearts of Springfield's citizens everywhere: Arthur Crandall and his puppet Gabbo.
Armed with a catchy theme song and a hackneyed catchphrase (“I’m a bad little boy”), Gabbo was soon the flavor of the month and he put Krusty out of business in the process. But Crandall’s time quickly ran out when Gabbo called all the kids of Springfield “Little S.O.B’s” live on the air. This is one of the great episodes in the show’s history, and much of that has to do with the spectacular flame-out of Crandall and his foul-mouthed puppet.
21. Wiseguy
First appearance: “The Way We Was” (Season 2, Episode 12)
Notable appearance: “Duffless” (Season 4, Episode 16)
Voiced by: Hank Azaria
The Simpsons is notorious for featuring similar-looking background characters in multiple jobs and roles during its 20+ year run, and the most memorable of all of these is what fans have dubbed the Wiseguy. He appears in dozens of episodes, yet all we get from him is a sarcastic remark or two delivered with impeccable comic time. It’s not until you've been watching the series for years that you notice that this odd character is a constant presence in the Simpson's lives, most notably as the limo driver at Homer’s prom in “The Way We Was,” the exterminator who fumigates the Van Houten house in “Bart Sells His Soul,” and as the pet store clerk who sells Lisa a hamster in “Duffless.”
He may be lowly and unimportant in the grand scheme of the show, but his nasty disposition and penchant for mockery typifies what the show is all about. And with Hank Azaria doing his best Charles Bronson impression for the voice, the Wiseguy should take his rightful place among the more memorable characters in Springfield.
20. Colonel Leslie “Hap” Hapablap
First appearance: “Sideshow Bob’s Last Gleaming” (Season 7, Episode 9)
Voiced by: R. Lee Ermey
When the writers of The Simpsons needed to fill the role of Colonel Leslie “Hap” Hapablap for “Sideshow Bob’s Last Gleaming,” the producers did the natural thing and secured R. Lee Ermey. Modeled after Ermey’s character in Full Metal Jacket, Hapablat is a fast-talking, crass military man who spews out priceless quotes faster than viewers can process them. Ermey brings the same electric qualities he featured in Kubrick’s masterpiece, expect this time his dialogue is much more Simpsonian.
Rants like “Sweet Enola Gay, son! I'm going to come in there and corpse you up—corpse you up and mail you to mama!” and “We've searched this airbase from top to bottom, and all we've found is porno, porno, porno," make him stand out from the countless other guest stars that have appeared on the show.
19. John
First appearance: “Homer’s Phobia” (Season 8, Episode 15)
Voiced by: John Waters
Leave it to The Simpsons to be one of the first American TV shows to tackle the topic of homosexuality head-on by introducing the character of John, aptly voiced by John Waters, in the episode “Homer’s Phobia.” Much of the characters strength comes from Waters, who obviously had a vested interest in turning John into one of the great Simpsons one-off characters ever.
Waters manages to bring his singular personality to the voice acting in this role; the animators and writers simply had to keep up with his performance and ad-libs. Best of all, Waters and the show’s crew managed to make John fit seamlessly into the Springfield universe without his character ever getting too preachy about the serious, real world themes.
18. Todd Flanders
First appearance: “Simpsons Roasting on an Open Fire” (Season 1, Episode 1)
Notable appearance: “Dead Putting Society” (Season 2, Episode 6)
Voiced by: Nancy Cartwright
One of the great dynamics in The Simpsons is the fact that this heathen family lives directly next door to the Flanders family, Springfield’s resident Bible thumpers. And while the clash between Homer and Ned is a given highlight of the series, the relationship between their sons has provided us with just as many classic moments. And between the two Flanders kids, Todd outshines his older brother Rod.
Todd's so saccharine that you can’t help but want to simultaneously punch and box him up like a Christmas present. Some of great Simpsons moments include his participation in a mini-golf tournament against Bart, and when he got swept away by a raging river while playing baby Moses in Ned’s directorial debut. But unlike the other members of his family, Todd is very impressionable and often gets corrupted by the outside world. Even then, he’s still the most relentlessly naïve and innocent character that the town has to offer. Jokes ensue.
17. Jasper Beardley
First appearance: “Homer’s Odyssey” (Season 1, Episode 3)
Notable appearance: “The PTA Disbands” (Season 6, Episode 21)
Voiced by: Harry Shearer
Jasper Beardly has one of the more peculiar existences on The Simpsons. He says little and never does anything terribly important, but he’s been a part of some of the best gags ever featured on the show. In “Lisa the Simpson,” Jasper is involved in a completely out-of-left-field subplot where he locks himself inside the freezer of the Kwik-E-Mart so he can be thawed out in the future. Once frozen, Apu slaps a Viking helmet on his head, dubs him Frostillicus, and charges people to see him.
However, his most famous moment comes in “The PTA Disbands,” when he's among the adults from town that the school gets to replace its striking faculty. Instead of teaching the children, Jasper stands at the front of the class, paddle in hand, telling the students which misdeeds will earn them a paddling. We can’t do it justice in words, so check it out here.
16. Lyle Lanley
First appearance: “Marge vs. the Monorail” (Season 4, Episode 12)
Voiced by: Phil Hartman
Conan O’Brien made a name for himself in Hollywood as a writer on The Simpsons in the early ‘90s. His credits include “New Kid on the Block” and “Homer Goes to College” (one of our favorites), but he's best known for “Marge vs. the Monorail.” In this gem, a nod to The Music Man, Springfield is swindled out of $3 million by a shifty businessman named Lyle Lanley, who builds a shoddy monorail for the town that Homer is hired to conduct.
Voiced by the legendary Phil Hartman, Lanley is nothing more than a lowly carnival barker in a candy cane striped suit with the uncanny ability to break into spontaneous song and dance. The combination of Hartman’s voice and Conan’s writing is the perfect blend of absurdity and cynicism, and it helped turn Lanley into one of our favorite, if not overlooked, characters.
15. Sideshow Mel
First appearance: “Itchy & Scratchy & Marge” (Season 2, Episode 9)
Notable appearance: “Bart Gets Famous” (Season 5, Episode 12)
Voiced by: Dan Castellaneta
Though he's constantly overshadowed by his murderous predecessor, Sideshow Mel has his fair share of bright spots. With his Shakespearean accent and trademark bone (which got stuck after trying to get gum out of his hair), Mel has solidified himself as a constant source of classic quotes and ridicule over the years. He's a constant target for Krusty the Clown’s violent temper, having been humiliated and abused both behind the scenes and in front of a national audience.
We love a good punching bag, and Mel is one of the best. When he’s not the butt of Krusty’s jokes, he can be seen around Springfield getting involved in many civic duties, such as town hall meetings and clearing Waylon Smithers’ name after he was accused of shooting Mr. Burns.
14. Dr. Nick Riviera
First appearance: “Bart Gets Hit By a Car” (Season 2, Episode 10)
Notable appearance: “Homer’s Triple Bypass” (Season 4, Episode 11)
Voiced by: Hank Azaria
With his famous “Hi everybody!” and dangerous lack of medical knowledge, Dr. Nick Riviera was, at one point, a premier supporting character on The Simpsons. With time, we've seen less and less of Dr. Nick, to the point that we now cherish what little screentime we actually get of him. When he was appearing regularly, his highpoint came during “Homer’s Triple Bypass,” where he attempted to save Homer’s life with a triple bypass surgery, only to need guidance during the operation from Lisa.
We miss his incompetency and his immoral corpse stealing, but most of all we miss his cheap infomercials advertising cheap surgeries (remember, his phone number is 1-600-DOCTORB—the extra “B” is for bargain!).
13. Üter Zörker
First appearance: “Treehouse of Horror IV” (Season 5, Episode 5)
Notable appearance: “Lisa on Ice” (Season 6, Episode 8)
Voiced by: Russi Taylor
Of all the notable school chums of the Simpson kids at Springfield Elementary, few come close to matching the brilliance of the rotund German exchange student Üter Zörker. Heavily inspired by Augustus Gloop, of Willy Wonka fame, Üter is a chocolate-filled butterball who's been a part of numerous classic moments since his debut in “Treehouse of Horror IV.”
How can you stay quiet at the sight of a bosomy Üter getting chased through a locker room by a towel-snapping Homer? Or the time he was killed by Lunch Lady Dorris and Principal Skinner and turned into Üterbraten? Every line out of his mouth is a gem, and though we understand the fascination everyone has with Milhouse and Ralph, it’s about time Üter gets the respect he deserves.
12. Duffman
First appearance: “The City of New York vs. Homer Simpson” (Season 9, Episode 1)
Notable appearance: “Hungry, Hungry Homer” (Season 12, Episode 15)
Voiced by: Hank Azaria
With his pelvic thrusts and constant shouts of “Oh yeah!” Duffman earn's his role as the icon of Duff beer drinkers across Springfield. Modeled after Budweiser’s former corporate mascot, Bud Man, Duffman’s sole responsibility is acting as a pawn for the Duff Corporation. Armed with a bright red cap and a utility belt stocked with frosty cans of beer, he travels from bar to bar shoving golden pilsners down the throats of barflies across town.
In typical Simpsons fashion, there's an aura of mystery about Duffman, too. The first Duffman’s real name was Barry Duffman, but since then he's been replaced by other Duffmen, who have all been equally blonde and enthusiastic. As Duffman once famously said, "Duffman can never die! Only the actors who play him!” Even more disturbing, he's under the assumption that he has children, appropriately named Dufflad and Duffgirl, only to find out that they were simply characters from a Super Bowl commercial he starred in years ago. There is something tragic behind those stylish sunglasses that just brings us joy.
11. Agnes Skinner
First appearance: “The Crepes of Wrath” (Season 1, Episode 11)
Notable appearance: “The Twisted World of Marge Simpson” (Season 8, Episode 11)
Voiced by: Tress MacNeille
In nearly every episode Agnes Skinner appears in, she delivers the quote of the night. And yet viewers fail to recognize her brilliance. She’s a crass and overbearing mother, whose mission in life is to emasculate her son, Principal Skinner, whenever she gets the chance. His unsettling, Norman Bates-esque relationship with her is still one of the best things on the show.
Whether she's berating Seymour for his dead-end job, mocking him for not having a computer full of pornography, or arguing with him over the use of their infamous bath pillow, Agnes is a tactless old bat with absolutely no redeeming qualities. And that's why we love her.
10. Superintendent Chalmers
First appearance: “Whacking Day” (Season 4, Episode 12)
Notable appearance: “22 Short Films About Springfield” (Season 7, Episode 21)
Voiced by: Hank Azaria
There's no man more frustrated with his job in Springfield than Superintendent Chalmers, or Super Nintendo Chalmers, as Ralph likes to put it. His frequent run-ins with Principal Skinner, Edna Krabappel, and Bart have solidified his legacy as one of the show’s great supporting characters. His charm ultimately lies in his being one of the few normal characters on the show. He’s just an ordinary man out to do his job, yet he’s constantly beaten down by the incompetence of the people surrounding him.
Chalmers is the ultimate straight man of this duo, and his exasperation with the over-extended Principal Skinner almost always boil over until Chalmer is screaming “Skinerrrr!” We have to hand it to Hank Azaria on this one for being able to make such real frustration a joy to listen to.
9. Captain Horatio McCallister (a.k.a. The Sea Captain)
First appearance: “New Kid on the Block” (Season 4, Episode 8)
Notable appearance: “The Mansion Family” (Season 11, Episode 12)
Voiced by: Hank Azaria
We have absolutely no idea where Springfield is located. Sometimes it’s next to a desert, sometimes it’s near a snow-capped mountain range, and sometimes it’s a coastal town by the ocean. It's that last location that leads to the Sea Captain. Unlike other characters on the show, the Sea Captain hasn’t had his personality fleshed out over the years with entire episodes dedicated to him. Still, we love watching him wreck ocean liners full of hot pants, or try to sell a 90-track CD he recorded of famous sea shanties on public-access television.
Ironically enough, the Sea Captain’s only notable contribution to the town can be found on land in his very own restaurant, The Frying Dutchman. The Captain’s most famous appearance on the show comes in “New Kid on the Block,” where he offers his customers an all-you-can-eat seafood deal that Homer attempts to take advantage of before being thrown out for eating the Captain into the red. This leads the Captain to respond, “Tis no man. 'Tis a remorseless eatin' machine.”
8. Reverend Lovejoy
First appearance: “The Telltale Head” (Season 1, Episode 8)
Notable Appearance: “In Marge We Trust” (Season 8, Episode 22)
Voiced by: Harry Shearer
It’s no secret that the people of Springfield are almost all dangerously unqualified for their jobs, and in no character is this more evident than Reverend Timothy Lovejoy, the local minister at The First Church of Springfield. Problem is, he openly disdains all things Christian. As his character has progressed, Lovejoy has been a conduit for the writers of the show to channel their frustrations with organized religion.
This is a man of the cloth who has called the Bibe “a 2,000 page sleeping pill” and claims that all religions are pretty much the same. In the episode “In Marge We Trust,” we learn that Lovejoy’s formerly idealistic views of the world had grown jaded because of his constant run-ins with Ned Flanders, whose devotion to religion had sapped Lovejoy of his passion for it. But, of course, instead of trying to find inspiration for his problems in the Bible, Lovejoy simply takes out his frustrations by letting his dog do his sinful business on Ned’s lawn.
7. Shary Bobbins
First appearance: “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious” (Season 8, Episode 13)
Voiced by: Maggie Roswell
Despite only appearing in one episode, Shary Bobbins has become one of the more notable obscure characters among hardcore fans. She debuts as a thinly-veiled parody of Mary Poppins after becoming a nanny to Bart, Lisa, and Maggie when the stresses of being a housewife leave Marge with PTSD. With a tune in her heart and a saccharine outlook on life, Bobbins attempts to bring peace and harmony into the Simpson household.
Unfortunately for her, she's never met the likes of this dysfunctional family before, and soon turns to alcohol as a way to cope with the misery of the household. In the end, Bobbins is left broken, the kids don’t learn a single lesson, and Marge resigns herself to a life of stress and anxiety. It’s an ending that typifies the nihilistic existence of The Simpsons, and is capped by the terrific sight gag of Bobbins being sucked into a jet engine as she slowly drifts away in her flying umbrella.
6. Hans Moleman
First appearance: “Principal Charming” (Season 2, Episode 14)
Notable appearance: “A Star Is Burns” (Season 6, Episode 18)
Voiced by: Dan Castellaneta
It’s not easy being Hans Moleman. Over the the course of the series, he's been killed multiple times (only to return in a later episode), pelted in the groin with a football all for the sake of cinema, and kissed repeatedly by Homer, who claims he tastes like a peanut. He may have started out as a forgettable background character, but we've grown to love watching his misfortunes unfold in front of us like a grisly car wreck. Though he has the body of an 80 year old, Hans is actually 31, but a lifetime of severe alcoholism has transformed him into a shriveled mess of sadness.
5. Gil Gunderson
First appearance: “Realty Bites” (Season 9, Episode 9)
Notable appearance: “Natural Born Kissers” (Season 9, Episode 12)
Voiced by: Dan Castellaneta
In a town full of drunks, losers, criminals and deadbeats, Gil Gunderson outshines them all as the lowliest citizen Springfield has to offer. First appearing as a co-worker at the real estate agency where Marge worked at in “Realty Bites,” Gil now slinks from job to job across various episodes, including a used car dealer, mall Santa, and farmer.
Frequently referring to himself in the third person as "Ol’ Gil," Gil is usually shown right before some unspeakable horror is about to befall him. We's seen him shot, forced to dance for nickels, and seemingly killed in a car accident. However, fate has a way of sparing his life just so he can live to see the humiliation of another day.
4. Kirk Van Houten
First appearance: “Bart’s Friend Falls in Love” (Season 3, Episode 23)
Notable appearance: “A Milhouse Divided” (Season 8, Episode 6)
Voiced by: Hank Azaria
The life of Kirk Van Houten could easily be called an American tragedy: He’s a balding, middle-aged man who gets divorced, fired, and has his musical dreams crushed all within the span of a 30 minute episode, the formidable “A Milhouse Divided.” Yet in the twisted world of The Simpsons, Kirk's failings are designed specifically for our amusement, and witnessing his misery has become one of the show’s greatest pleasures over the years.
Kirk is best known as the father of Milhouse Van Houten, Bart’s best friend. Milhouse is anything but underrated, but for our money Kirk is the real standout of the family. He's a former major player down at Southern Cracker, until his life falls apart and he's forced to sleep in a race-car bed in a derelict bachelor pad with the rest of the town’s sad-sack single men. Since then, Kirk has evolved into the show’s resident punching bag.
3. Hank Scorpio
First appearance: “You Only Move Twice” (Season 8, Episode 2)
Voiced by: Albert Brooks
If you ever wondered what would happen if Bill Gates suddenly turned into a maniacal Bond villain, look no further than Hank Scorpio. As the owner of the Globex Corporation, Scorpio is both a savvy businessman and a twisted megalomaniac armed with a laser satellite system capable of turning any major city to dust. Of course, he also happens to be Homer’s boss for an episode. Voiced by the brilliant Albert Brooks, Scorpio possesses a collection of memorable quotes, a handsome beard, and a sociopathic personality.
For some reason this supremely brilliant and wealthy mad man takes a shine to Homer, who's completely oblivious to his new boss’ murderous streak, despite having ringside seats to Scorpio’s final throwdown with the U.N. From hammocks to homicide, Scorpio is the perfect blend of sharp writing and pitch-perfect voice acting by Brooks, who manages to make a mass murderer sound like the world's best boss.
2. Kent Brockman
First appearance: “The Telltale Head” (Season 1, Episode 8)
Notable appearance: “Deep Space Homer” (Season 5, Episode 15)
Voiced by: Harry Shearer
It makes sense that the ludicrous residents of Springfield would have an equally dim-witted news anchor to report on their absurd exploits every week. As the main media personality on Channel 6, Kent Brockman is the perfect talking head to simultaneously sensationalize and trivialize all of the events of Springfield. Over the years his memorable moments include winning the lottery live on the air, being nearly fired for on-air profanity (“That ought to hold those little S.O.B’s”) and refusing to read the news one evening after Bart stole his danish.
None of those incidents, however, compare to Brockman’s most iconic moment among Simpsons fans, when he erroneously welcomes a horde of what he thinks are an invading army of mutant space ants to Earth in “Deep Space Homer.” With the line “And I, for one, welcome our new insect overlords,” Brockman propels himself from flat background character into one of the show’s more notable residents.
1. Frank Grimes
First appearance: “Homer’s Enemy” (Season 8, Episode 23)
Voiced by: Hank Azaria
Frank Grimes may only show up in one Simpsons episode, but it's one of the best the series has to offer. The episode in question? “Homer’s Enemy,” which revolves around what happens when Grimes, an average hardworking Joe from the real world, gets dropped into Springfield and has to be co-workers with Homer at the nuclear plant. Grimes’ good-natured, industrious personality is quickly put to the test as he has numerous run-ins with Homer, his polar opposite.
Within the span of this dark and twisted story, Homer breaks Grimes down to the point of insanity, and we as an audience are left to wonder why it is that we actually love this dangerous oaf so much in the first place.
In the end, Frank Grimes was just an ordinary man who wound up letting the absurd nature of Springfield lead him to an early grave. Grimes’ life can be viewed as a tragedy, but as the show has taught us over the years, the line between the tragic and the comic is as thin as the hairs on Homer’s head.