Antagonists are a vital chemical to any successful TV show, as they help develop interesting storylines and character interactions. The Simpsons have their prolific 'bad guys' to keep things moving and to keep Homer using his brains. Sure, their intentions might be off-center, but they also help create some of the best episodes.
Sideshow Bob was honored recently as a Disney Villain, with Disney+'s drop of the newest The Simpsons short, The Most Wonderful Time of the Year. In the three-minute piece, the former Krusty the Clown star teamed up with other famous Disney villains for Halloween. It's a musical masterpiece performed by no other than the great Kelsey Grammer, reprising Sideshow Bob's iconic voice.
In addition to Sideshow Bob, let's take a look at some of the other villains who are just a "evil," but are so good at being "evil."
These 6 The Simpsons villains are iconic
Mr. Charles Montgomery Burns
Mr. Burns is Springfield's most powerful man, for he owns nearly every business and influences the town's spending (when he can). As owner and CEO of the nuclear power plant, he has little heart for his employees and keeping it up to code, as he's cheap, despite being a billionaire.
Then, there's his classic saying, "Release the hounds," when the invited and uninvited steps foot on his property before they're running for their lives from a pack of Dobermans,
While Burns makes life miserable for others, especially Homer, he does have some humane qualities. One example is when he adopted Smithers as an infant following his father's death, and another is when he changes his mind about making a coat out of greyhound fur.
I don't know why Burns would conceive such an idea, as greyhounds shed and its inhumane.
Hank Scorpio
Hank Scorpio is a one-shot character who appears only in the season 8 episode "You Only Move Twice." While Scorpio treats his Globex Corp. employees far better than Burns, he's an evil genius in disguise and a terrorist. He has a hatred for the United States government and France, but he's deliciously likable because he's complex and has all the qualities of a perfect villain.
Fat Tony
Known as Springfield's equation to a gangster crime boss, Fat Tony and his gang have cooked up every racketeering business and scandal. He does make a great frenemy of Homer and his family, but for a crime boss, he hasn't committed any murders (that I know of).
Snake Jailbird
Known for his Southern Californian accent and the phrases "dude" and "bye," Snake Jailbird is always robbing the Kwik-E-Mart and getting arrested, although he's not imprisoned long. He has a spot for puppies and kids, leading us to believe that maybe he isn't such a bad guy—just a guy who makes bad choices.
Patty and Selma Bouvier
Marge's older twin sisters, Patti and Selma, are loving aunts and have a respectable employment at the Springfield DMV. Yet, they both antagonize their brother-in-law, Homer, viewing him as incompetent, lazy, and fat. However, both sisters secretly like Home, for he accepted Patty' lesbeinism and supported Selma's desire to adopt a baby girl from China.
Sideshow Bob
Perhaps known as the infamous villain in The Simpsons legacy and canon, Sideshow Bob has proven himself multiple times to earn his newly reigned title of Disney Villain. Why? He's always after Bart for foiling his framing of Krusty, his candidacy for Springfield mayor, and his attempt to murder Selma on their honeymoon.
But there were a few occasions in which Bob helped Bart and Lisa, such as escaping from a collapsing dam and helping solve the case of the missing Christmas gifts. However, he swiftly reverts to his old criminal ways.