The Simpsons has been entertaining audiences around the globe since 1989, beginning as a fractured look at modern suburban America through the lens of one peculiar family. Over time, it became a cultural landmark that set trends and even predicted the future at times.
The Simpson family's adventures have involved fights against social inequalities, cultural differences, school bullies, and good old-fashioned out-and-out villains. From Mr. Burns to Sideshow Bob, they've gone up against Springfield's best and funniest enemies on many occasions.
Many characters in The Simpsons skirt the line between good and evil. Here's our look at the best villainous and antagonistic characters in the iconic animated series' multi-decade run.
7. Patty & Selma
Not so much dastardly villains as they are major nuisances to both Homer and audiences, Patty and Selma have done some horrible things to Homer (and he's gotten back at them on many occasions, too).
In "Homer vs. Patty and Selma," Homer loses a lot of money on a foolish pumpkin investment and turns to Patty and Selma for aid, which they give. But they start treating Homer as their slave, demanding that he perform all manner of terrible things for them—like rubbing their gross feet.
The enduring war between Homer and Marge's sisters doesn't ever extend to the rest of the family to any notable degree, except for when they have Homer's tombstone made when they believe he's died (which Marge chastizes them for, calling them "ghouls").
6. Nelson Muntz
As The Simpsons went on, Nelson's role as the neighborhood bully remained steadfast, although not as potent as it once was. Still, looking back at the first seasons of the show, Nelson is a threat to Bart and his schoolmates as he terrorizes them on a daily basis.
During the season one episode "Bart the General," Nelson beats up Bart after school because Bart defends Lisa from one of Nelson's cronies. Though Bart attempts to fight back in various ways, it's futile—so he forms an army of other children to deal with Nelson's menace.
The plan works, with Nelson attacked by seemingly dozens of school students who tie him up, with Bart parading him down the street. While Nelson remains a lesser bully now, it's good to remember that he was once a tyrannical monster that had to be stopped.
5. Hank Scorpio
Hank Scorpio is a real villain, even if he's not one whom the Simpson family is directly opposed to at any point.
Hank Scorpio runs the Globex Corporation, which enlists Homer to work in their nuclear division, with Homer blissfully unaware of what he's getting into with Scorpio. Homer and Hank form a close bond, with Scorpio using his charm to motivate Homer into doing a good job.
However, when Scorpio threatens the United Nations and murders Mr. Bont (a James Bond parody), the government attacks—after which Scorpio seizes the East Coast.
Despite his villainy, Scorpio cared for Homer. He even bought him the Denver Broncos when Homer decided to move back to Springfield.
4. Ms. Botz
The Babysitter Bandit herself is drafted by Homer and Marge to watch Bart, Lisa, and Maggie for the night as the couple take a much-needed romantic night for themselves.
Of course, Homer and Marge have no idea that Ms. Botz is Lucille Botzcowski using "a clever alias" to disguise her name. When the bandit reveals herself to Bart and Lisa, she meets with resistance but is able to tie up the children.
However, she forgets about Maggie, who frees Lisa and Bart. The trio then lure the bandit into one of their rooms—and when the evil Ms. Botz walks in, Bart cracks her over the head with a baseball bat.
Though Homer lets her go by accident and then tries to lie about it on national TV, the villain is a brilliant character who only appeared once.
3. Russ Cargill
When the long-awaited Simpsons movie became a reality, it needed a big villain to oppose the family—a tyrant who would pose a threat that required the family to work together to defeat him. Enter, Russ Cargill.
The (psychotic) head of the Environmental Protection Agency, Russ Cargill traps the town of Springfield under a giant dome after Homer pollutes the lake over the tipping point for a free donut.
The family escapes the dome when the town realizes that Homer is the person responsible, but eventually return to defeat Cargill when they realize he plans to destroy Springfield.
Cargill became a wonderful cinematic enemy for the family to face. And Albert Brooks—who also voiced Hank Scorpio—lends his voice to the character hilariously.
2. Sideshow Bob
Perhaps the best animated psychopath in history, Kelsey Grammer's Sideshow Bob tried to frame Krusty the Clown for armed robbery, only to find himself foiled by Bart and Lisa (and Bart exposed him on TV).
Following the events of "Krusty Gets Busted" in season one, Bob has focused all his efforts on mercilessly killing Bart, with his best attempt on Bart's life coming in "Cape Feare."
During the hilarious Cape Fear parody, he ties up Homer, Marge, Lisa, and Maggie, cornering Bart on the boat that the family has procured via the Witness Relocation Program.
Bart, of course, appeals to Bob's vanity, who sings the entirety of the HMS Pinafore opera before the boat drifts into Springfield and by Chief Wiggum's bust of a local brothel.
1. Mr. Burns
Charles Montgomery Burns is the Darth Sidious, the evil overlord, the brutal kingpin of Springfield, the show's greatest adversary. His exploits have seen him attempt to kill people, kidnap the missing Brazilian soccer team, and block out Springfield's sun for personal wealth.
The whole town has had a turn with Mr. Burns at one point or another, with the businessman and power plant owner never satisfied with his enormous fortune and always seeking more.
As with every great villain, Mr. Burns isn't beyond understanding. Indeed, his life is brilliantly parodied against Charles Foster Kane's own story from Citizen Kane via the episode "Rosebud."
Furthermore, Mr. Burns is the only Springfield villain who appears capable of success in his plans, with his faithful servant Smithers at his side.