11 Iconic ‘Simpsons’ Villains Who Wreaked Havoc in Springfield
Murder, mayhem, and general mischief regularly disrupt the lives of the Simpsons and the citizens of Springfield, thanks to a colorful cast of nogoodniks who bring chaos wherever they go. Ranging from petty crooks to would-be world dominators, these villains each add their own unique brand of trouble to the town that has seen its fair share of bedlam.
While some of these miscreants return time and again to seek revenge against Fox’s first family of animation, others appeared in just a single, memorable episode of The Simpsons, yet left a strong enough impression to create a lasting mark on pop culture.
Here is a look at the various villains to ever darken the doorstep of the Simpson family doorstep.
Kang and Kodos
Full Name: Kang and Kodos Johnson
Voiced By: Harry Shearer and Dan Castellaneta
Kang and Kodos appear almost exclusively in the “Treehouse of Horror” episodes, where they routinely wreak havoc on the citizens of Springfield and the planet Earth. They have rigged U.S. presidential elections, forced Marge (Julie Kavner) into alien breeding schemes, attempted multiple invasions, and tried to enslave humanity with varying degrees of success.
The Devil Flanders
Full name: Nedward “Ned” Flanders Jr.
Voiced by: Harry Shearer
“Flanders! You’re the devil?” “It’s always the one you least suspect.” Devil Flanders has some of the most memorable kills in the series, thanks to his full arsenal of satanic powers. He first appears in “Treehouse of Horror IV,” when Homer trades his soul for a donut and the Devil, disguised as Ned Flanders, shows up to seal the deal. While he occasionally appears as Chernabog from Fantasia, it’s the Flanders version that’s most iconic, retaining Ned’s trademark cheerfulness while carrying out the duties of Hell. He’s made multiple cameos across the “Treehouse of Horror” series and appeared in the installment “Heck House,” where he asks the Lord for permission to teach Springfield’s kids a lesson by “psychologically torturing them into loving you.”
Lyle Lanley
Full name: Lyle Lanley
Voiced by: Phil Hartman
In “Marge vs. the Monorail,” Lyle Lanley sells the town on a monorail with a nifty little song and dance about the future of travel. However, Lyle sells Springfield a shoddy, dangerous monorail, cutting corners at every turn and pocketing the money. While escaping with his cash, his plane lands in North Haverbrook, one of his last marks, where the townspeople are waiting for him with pitchforks and torches.
Frank Grimes Jr.
Full name: Frank ‘Grimey’ Grimes Jr.
Voiced by: Hank Azaria
Introduced in “The Great Louse Detective,” Frank Grimes Jr. is the illegitimate son of the late Frank Grimes and an unnamed sex worker. Determined to avenge his father’s death, he makes several attempts on Homer’s life, including cutting the brakes on his car, trying to trap him in a gym steam room, and finally confronting him at the Springfield Costume Ball. In an unexpected twist, Sideshow Bob (Kelsey Grammer) teams up with the police to track down Frank Jr. and ultimately foils the attack, saving Homer in the process.
Frank Grimes
Full name: Frank “Grimey” Grimes
Voiced by: Hank Azaria
Frank Grimes has a rough life. Abandoned as a child, he starts working while other kids are playing in sandboxes. He survives a silo explosion that leaves him scarred, grows up in poverty, and earns a nuclear science degree through correspondence courses. From the moment he meets Homer, he despises him, viewing him as an incompetent buffoon who somehow has everything Grimes ever wanted: a dream house, a loving family, and a Grammy. After a failed attempt to expose Homer as a dunce, Grimes suffers a breakdown and dies while recklessly mimicking Homer’s behavior, electrocuting himself on high-voltage wires. He later reappears in “Treehouse of Horror XXVII” as a vengeful spirit who teams up with either Kodos or Kang and Sideshow Bob, only to have their plan foiled by a knife-wielding Maggie.
Hank Scorpio
Full name: Hank Scorpio
Voiced by: Albert Brooks
The nicest supervillain you’ll ever meet. Though he only appears in a single episode (“You Only Move Twice”), Hank Scorpio is one of the best bosses Homer ever has, despite being a megalomaniacal evildoer hellbent on world domination. From his base in the idyllic town of Cypress Creek, Scorpio runs Globex Corporation, treating his employees with respect and kindness while casually unleashing global mayhem and doomsday weapons. When Homer leaves his job, Scorpio thanks him for his service with a surprising parting gift: ownership of the Denver Broncos.
Fat Tony
Full name: Anthony “Fat Tony” D’Amico
Voiced by: Joe Mantegna
The leader of Springfield’s local crime syndicate, Fat Tony has his hands in racketeering, bootlegging, extortion, illegal gambling, and the occasional insurance scam. He meets his end in Season 22 (“Donnie Fatso”) after suffering a fatal heart attack while in police custody upon discovering that his close friend Homer is an FBI informant. His cousin, Fit Tony from San Diego (also Mantegna), takes over the operation and eventually adopts the name Fat Tony himself after the stresses of mob life lead to stress eating.
Snake Jailbird
Full name: Chester Turley, Albert Knickerbocker Aloysius Snake
Voiced by: Hank Azaria
More of a career criminal than a supervillain or a threat to the larger community, he is best known for robbing the Kwik-E-Mart, Moe’s Tavern, and the vending machines at Springfield Elementary. He has also carjacked Marge’s pretzel wagon, stolen the Simpson family’s grocery-getter, and once broke into a beauty pageant to steal the crown. He’s also something of a firebug, often using fire either as a means of escape or as part of a larger scheme.
Sideshow Bob
Full name: Robert Underdunk Terwilliger
Voiced by: Kelsey Grammer
During his long life of crime, Sideshow Bob has framed Krusty the Clown (Dan Castellaneta) for armed robbery, attempted to murder Bart (Nancy Cartwright) on multiple occasions, tried to kill Aunt Selma (Julie Kavner) for her inheritance, hypnotized Bart into attempting to assassinate Krusty during a school broadcast, rigged an election to torment the Simpsons, and even stolen a nuclear bomb to hold Springfield hostage in a plot to force residents to change their television habits. A criminal mastermind, his repeated failed attempts to murder a 10-year-old has made him one of the show’s most iconic and theatrical antagonists.
Mr. Burns
Full name: Charles Montgomery Burns
Voiced by: Harry Shearer
A top-tier villain among Springfield’s evildoers, Mr. Burns is arguably the worst scoundrel to ever set foot in the fictional town. Universally despised for his endless misdeeds, he has blocked out the sun to boost reliance on his nuclear plant, failed a safety inspection with 342 violations, attempted to replace workers with greyhounds, and even tried to make a tuxedo out of puppies. He once goes so far as to steal candy from a baby, a moment that leads to his infamous shooting. Beyond targeting the Simpson family, he has repeatedly tried to destroy Springfield itself for his own personal gain. He’s also a terrible, terrible boss.
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