Top 20 Greatest Villains In Simpsons History

Hes one of the pettier villains, to be sure - but a corrupt politician is still a corrupt politician. Joe Quimby is the mayor of Springfield, a politician so corrupt his seal is literally Corruptus in Extremis. Apart from his numerous illegitimate children and his easy acceptance of bribes, Quimby also shows contempt for his constituents. He cant even hold his own in a debate against the likes of Sideshow Bob. But in the end, even when the citizens finally take over, he is still a fixture of Springfield. And to think, he is a parody of Ted Kennedy and the Kennedy family in general. Ouch.

Sometimes villains are so vivid and full of life, they are memorable even if they only appear in an episode or two. When Bart gets unhealthily fat and gets a heart attack, his family sends him to Serenity Ranch fat camp. Its head counselor, Tab Spangler, is determined to get the campers to lose weight with tough luck. Spangler is a jerk with a short temper and openly bigoted toward plus-size people. He is also hypocritical, willing to break his no-fast-food diet for a bite of Homers cheeseburger. What an entertaining scoundrel.

Criminal or not, this villain is an artist. Crowley was sent to prison for shooting Apu, but his down-to-earth politesse and his phenomenal painting skills gave him a second chance at redemption. Advocated by a sympathetic Marge, he is released. When Principal Skinner hired him to do a mural, however, Crowleys artistic vision and Skinners did not align at all. Enraged at the poor reception of his mural and being given the blame for it, Crowley burns it all down. He also burns down Skinners car for good measure. So much for redemption, but hes a villain you dont forget easily.

Bart discovers a world of pure imagination when he meets this Willy Wonka send-up. After Barts T-shirt business is shut down, Goose Gladwell offers to sell the shirts at his shop. But Gladwells dark side rears its ugly head when he sells the rights to Barts shirts to the biggest baddy of them all: Disney. And of course, Bart doesnt get a penny from the sales. It was Homer, of all people, who managed to talk some sense into this quirky trickster. Gladwell was a Green Beret in Vietnam, which does explain everything.

Marges marriage to Homer isa mixed bag, to say the least. But she could have done way worse. Artie Ziff was Marges prom date; they were even crowned prom king and queen. But Artie has a dark side, as shown when he rips Marges dress in his boundary-traversing lust. Years later, Artie is now the fifth-richest man. He is still very much obsessed with Marge, even offering her a million dollars to spend a weekend with her. His forceful ways rear their ugly heads once more, though, and Marge refuses him again. As a seeming apology, he gives Homer a device to fix his snoringwhich doubles as a secret camera, spying on Marge and giving her subliminal messages. What a delightfully-written creep.

Villainy sometimes runs in the family. Thats the case at least with Sideshow Bobs whole family, including his cute son. But his brother is a good competitor for Bobs villainy. After his release from prison, Sideshow Bob rooms with his brother, Cecil, also effete, eloquent, and with a tendency towards homicide. In fact, Cecil plans to frame Bob for the embezzlement of funds from Springfields dam project, intentionally constructed with poor materials. It turns out Cecil resents Bob for upstaging him at auditions as Krusty the Clowns sidekick. When Cecil is arrested, so is Sideshow Bob. Cain has nothing on this brother.

There should be more love towards the classic Simpsons episodes. The shows greatness was apparent even in this season one finale, where Bart and Lisa get a babysitter from hell. The surly Ms. Botz turns out to be a wanted burglar, the Babysitter Bandit, in fact. Botz ties them up, but luckily Maggie saves her siblings. Bart knocks her out with a baseball bat, but Ms. Botz escapes when Homer and Marge arrive home, mistakenly believing her to be a victim. Its a shame she only appears in this one episode; her villainy game was strong.

Who can forget this adolescent trio? While they dont get as much development or plot lines as main tormentor Nelson, these three get plenty of hilariously villainous moments. Most of their crimes involve juvenile delinquency, such as convincing Bart to cut off the head of Jebediah Springfields statue in Season One. The years, though, have shown a softer side to these three. Dolph is an accomplished polyglot, Jimbo is the mastermind with a bad home life, and Kearney is an ex-convict and the father of a teenager. And of course, their parents are of the same bad strain.

This cat is one hell of a burglar. He is introduced in this Season 5 episode, stealing Lisas saxophone, Barts stamp collection, and Marges necklace in one fell swoop. He even stole Flanders Shroud of Turin beach towels. When Molloy finally gets arrested after stealing the worlds biggest zirconia, he sends the townspeople on a wild goose chase towards a hidden treasure. The treasure was just a piece of paper, explaining the plot so that Molloy could escape jail unseen. Molloy is definitely one of the most clever of the shows minor villains.

Did you know that the Simpsons writers had considered making Hank Scorpio the villain for the 2007 movie? Great as Scorpio is, were glad this brand-new villain was created. When Springfield is faced with a pollution crisis, Cargill comes in as head of the EPAto make it worse. One option he presents to President Arnold Schwarzenegger is to seal the city in a glass dome. Furious at the residents attempts to destroy the dome, Cargill tricks the president to order the towns destruction. And as a linchpin to his villainy, Cargill also tries to kill Homer and Bart. Now this is a villain indeed.

Springfield has many colorful criminals, but one of its most recurring lawbreakers is Snake, whose last name is variously stated to be Turley or Jailbird. The latter is quite apt, as hes generally in and out of prison, though given the ineptitude of Springfields finest thats hardly surprising. An interesting twist on the career criminal archetype, Snake brings a lot of hilarity to otherwise tense situations, given his changeable attitude and surfer dude accent. Fond of fast cars and notoriously intolerant of singing and music that isnt rock and roll, Snake is one premium villain, dude.

An unlucky, hardworking co-worker of Homers at the nuclear plant, Frank Grimes only appears in one episode, but he makes a big, and dark, impression. Grimes gets to know Homer and is continually astonished that such a lazy, fat moron is able to get so far in life by accident when all his efforts have seemingly been for naught. Declaring himself Homers enemy, Grimes attempts to sabotage Homer, eventually leading the entitled man to become unhinged and to imitate Homers idiocy by touching electrical wires, which kill him. Grimes son even appears to carry on his fathers grudge against the dopey Simpson patriarch.

As Springfield Elementary Schools foremost meanie, Nelson Muntz is the quintessential childhood tormentor. Frequently beating up his classmates, including Bart, Milhouse, Martin, and even Lisa on occasion, Nelson never fails to mock someone when theyre down; usually with his signature laugh. Though generally dimwitted and brutish, Nelson is driven to lash out at others by his own insecurities and is sometimes shown to have a sensitive side. While hes threatening to other kids, adults can often knock him down to size and put him in his place.

The personable CEO of Globex Corporation, Hank Scorpio hires Homer to work for him in an idyllic planned community. Fast-talking and given to tangents, Scorpio is an ideal boss who motivates Homer to actually be good at his job. Theres just one problem hes a supervillain. Bent on conquering the world with doomsday devices and facing off against Bond style secret agents, Scorpio is completely evil to the outside world, even if hes nicer to his employees than most legitimate bosses. Though he only appears prominently in one episode, every scene hes in is incredibly entertaining. And, hes got a catchy theme song too!

The reverends daughter, while Jessica Lovejoy shows a goodie two shoes attitude to adults, shes actually a huge troublemaker, which is what attracts Bart to her and she to him. However, Bart eventually realizes that she has a lust for crime and danger that outstrips even his own. Her willingness to get him into trouble when he tries to distance himself from her leads her to become a formidable young femme fatale for him and Lisa. Her duplicitous nature and excellent acting skills should be no surprise either, given that shes voiced by regular Oscar winner, Meryl Streep.

A staple of The Simpsons Treehouse of Horror episodes, Kang and Kodos are a duo of terrifying tentacled, cycloptic aliens that may or may not be siblings. Most of the time, theyre shown to have malevolent intentions for the Simpson family and other Earthlings; often taking over Earth, either by hook or by crook. Like the anthology episodes they appear in though, theyre not always portrayed consistently, with their first appearance actually revealing them to be benevolent. Even so, their drooling, manic grins and booming voices make some of the lines they deliver quite frightening and funny.

When the town holds a meeting to decide what to do with money they won from a fine, theyre approached by Lyle Lanley, who quickly sells them on building a monorail with the aid of an incredibly catchy song. However, Marge and Lisa suspect that Lanley may be pulling one over on Springfield, and an investigation into his previous monorail endeavors reveals that hes a con artist in the vein of the musical The Music Man. Played to exuberant perfection by the late, great Phil Hartman, Lyle Lanley is a slick and slimy villain we were all glad to see get his just desserts.

Springfields resident mob boss, Fat Tony DAmico is one of the biggest criminals in town, frequently performing scams, extortion, and whackings that almost always see him come out on top. Few targets are off-limits, and he even once extorted an elementary school. Given how ruthless and threatening he can be, the moments when Fat Tony does say funny things are just that much funnier, since they clash with his tough guy image. While glimpses of a softer nature are there, he still remains one of The Simpsons most intimidating villains.

Bart might suffer through Nelson, but his arch nemesis is undoubtedly Robert Terwilliger Jr., better known as Sideshow Bob. A self-proclaimed genius with a perpetual vendetta against the Simpson boy, Bob is legitimately menacing and acts like a cross between Hannibal Lecter and Wile E. Coyote; always brilliant, but never able, or sometimes even wanting, to achieve his goal to kill Bart. Played spectacularly by Kelsey Grammer, Bob is sometimes rivaled by his brother, Cecil, but Bob comes out on top for us. Overall, Sideshow Bob is not just a great Simpsons villain: hes a great villain, period.

Charles Montgomery Burns is the richest man in town and indisputably its most hated. He's also Homer's boss. Selfish, cruel, and moneygrubbing, Mr. Burns has little sympathy for anyone and frequently endangers his employees, strangers, and often the entire town with his hateful whims. Whether hes releasing his hounds on visitors to his home or declining to donate money to charity, Mr. Burns oozes hateful, capitalistic greed. Even so, his antiquated views, forgetfulness, and daffy attitude can make him somewhat endearing. All in all, hes an excellent villain and arguably the best one on the show.

Which other villain from The Simpsons was excellentor simply deserves more love? Let us know in the comments down below!