Top 10 The Simpsons Villains

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 he’s generally in and out of prison, though given the ineptitude of Springfield’s “finest” that’s 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 isn’t rock and roll, Snake is one premium villain, dude.

An unlucky, hardworking co-worker of Homer’s 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 Homer’s enemy, Grimes attempts to sabotage Homer, eventually leading the entitled man to become unhinged and to imitate Homer’s idiocy by touching electrical wires, which kill him. Grimes’ son even appears to carry on his father’s grudge against the dopey Simpson patriarch.

As Springfield Elementary School’s foremost bully, 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 they’re 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 he’s 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. There’s just one problem – he’s 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 he’s nicer to his employees than most legitimate bosses. Though he only appears prominently in one episode, every scene he’s in is incredibly entertaining. And, he’s got a catchy theme song too!

The reverend’s daughter, while Jessica Lovejoy shows a goodie two shoes attitude to adults, she’s 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 she’s 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, they’re 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, they’re 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, they’re 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 he’s 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.

Springfield’s resident mob boss, “Fat Tony” D’Amico 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.

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 he’s 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, he’s an excellent villain and nearly the best one on the show.



Before we get to our top pick, here are a few honorable mentions:



Lucille Botzcowski





Molloy



Artie Ziff

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 Wil 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: he’s a great villain, period.