A recent episode of The Simpsons parodied Stephen King’s It with Krusty the Clown taking the place of Pennywise. Krusty isn’t typically portrayed as a villain – he’s more of a satire of the vanity of celebrities and the audacity of joke-stealing comedians – but plenty of fellow Springfieldians are depicted as diabolical baddies.
From Mr. Burns to Sideshow Bob to Hank Scorpio, The Simpsons is full of iconic villains. But some of them, like Fat Tony and Snake Jailbird, are more lovable than others, like the creepy Artie Ziff or the inhuman Kang and Kodos.
10 Artie Ziff
Marge’s only love interest before Homer was Artie Ziff, her creepy prom date who bragged about his “busy hands.” Artie ended up becoming rich and successful, but all that material success is meaningless in a world without Marge, so he’s dedicated his life to stalking her.
He tries to plant a video camera in Homer and Marge’s bedroom so he can watch Marge sleep. Voice actor Jon Lovitz hilariously leans into Artie’s most hateable qualities.
9 Kang & Kodos
Although The Simpsons began its life way back in 1989 as a relatively grounded show about relatable family situations affecting an upper-lower-middle-class couple with three kids, the writers quickly left behind any semblance of realism so they could explore more absurdist concepts.
Kang and Kodos are a pair of evil aliens determined to invade Earth. They sit in their ship above the Earth’s atmosphere, waiting for the right time to pounce and enslave humanity.
8 Lyle Lanley
Often named as the greatest episode of the entire series, “Marge vs. the Monorail” revolves around Springfield coming into some money and investing it in a dodgy monorail system. The monorail is pitched by Lyle Lanley, who’s already pulled the same scam on the nearby towns of Brockway, Ogdenville, and North Haverbrook.
By the time the town realizes the monorail is unsafe, Lanley has already skipped town. Lanley is a hysterical caricature of the “snake oil salesman” archetype.
7 Russ Cargill
Not every iconic Simpsons villain is confined to the series; the antagonist of The Simpsons Movie is also one of the show’s most memorable bad guys. Russ Cargill isn’t a megalomaniac in the mold of Hank Scorpio; he’s a wealthy environmentalist put in charge of the Environmental Protection Agency.
In a bid to prevent the spread of Springfield’s pollution, Cargill encases the town in a giant glass dome, trapping the citizens inside “like carrots.” Cargill is an unscrupulous, power-crazed villain, but Albert Brooks gets some dry laughs with his typically brilliant performance.
6 Snake Jailbird
Springfield’s resident petty crook, Snake Jailbird, has robbed just about every one of the town’s businesses, from the Kwik-E-Mart to Barney’s Bowlarama. Hank Azaria plays the character with a hysterical “Valley Boy” accent.
The love-hate relationship shared by Snake and Chief Wiggum makes them one of the funniest double acts in The Simpsons’ sprawling ensemble.
5 Molloy
Played by guest star Sam Neill, Molloy is the notorious “Springfield Cat Burglar” that Homer assembles a neighborhood watch to catch in “Homer the Vigilante.” As unlikely that it is for Homer to foil the elusive crook, he ends up putting Molloy behind bars with the help of his dad.
Molloy is a suave, smooth-talking charmer who steals from Springfieldians more for the thrill of the crime than the material gains of the heist. He also greatly enjoys his cat-and-mouse chase with Homer.
4 Fat Tony
The local mob in Springfield is run by powerful mafioso Anthony “Fat Tony” D’Amico. He’s a spot-on spoof of every gangster character from cinema history. Despite being a murderous mobster, Tony never fails to get a laugh whenever he’s on-screen.
Tony has plenty of hilarious moments in The Simpsons. Given the choice between binders based on Garfield and Love Is... to take out his enemy’s tires, Fat Tony says, “I prefer the cat. He hates Mondays. We can all relate.”
3 Sideshow Bob
Krusty’s diabolical former sidekick, Sideshow Bob, is unusually charming for a convict who’s dedicated his life to murdering a 10-year-old boy. After he framed Krusty for a crime he didn’t commit and Bart foiled the scheme, Bob became committed to exacting revenge.
Sideshow Bob isn’t always portrayed as a villain. When his brother Cecil came to town, Bob put a stop to his evil plan and saved Bart’s life in the process.
2 Mr. Burns
The most evil man in Springfield is impossible to hate. Mr. Burns might be stingier than Scrooge, colder than Mr. Freeze, and more cartoonishly unscrupulous than Blofeld, but he’s still one of The Simpsons’ most lovable characters.
Everything about Mr. Burns is exaggerated for comedic effect, from his age to his wealth to his archness. Plenty of episodes have made Mr. Burns a slightly sympathetic figure, like the one where he joins Homer’s bowling team or the one where he falls in love.
1 Hank Scorpio
In the fan-favorite episode “You Only Move Twice,” the Simpsons leave Springfield behind when Homer is offered a job working for a James Bondian supervillain named Hank Scorpio (also played by regular guest star Albert Brooks). Scorpio is surprisingly upbeat for a guy holding the United Nations to ransom.
He might blow up monuments and kill gentleman spies, but Scorpio is an encouraging, supportive employer who has more of a claim to the title of “world’s best boss” than Michael Scott.
Source:gamerant.com