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The worst things Mr. Burns has done on The Simpsons

There are few evil characters who delight in their villainy more than Springfield's very own perpetual antagonist, the excellent Charles Montgomery Burns. Voiced by the incomparable Harry Shearer, Mr. Burns has been a day one staple of The Simpsons since the show premiered in 1989. The old school tycoon is known for his immense wealth, ownership of the Springfield Nuclear Power Plant, and his old-timey schemes. His age is nebulous, but it's generally agreed upon that he's one old mogul who's at times both immensely frail and physically capable.

Largely considered to represent the worst of corporate America, Burns has developed over time into one of the more well-rounded characters on the show. However, unlike your typical Barney Gumble or Moe Syzlak, Burns' character development never sacrifices his general demeanor as a man who would've delighted in tying a woman to train tracks in a past life. But with a character so rooted in Simpsons history, it's hard to keep track of all the damnable deeds he's committed over the years without running the risk of being attacked by his loyal hounds. Still, to help curious fans, below is a rundown of some of the worst things that Mr. Burns has ever done on The Simpsons.

Mr. Burns blocked out the sun from Springfield

In one of his most diabolical and high-profile acts of Bond-level villainy, Mr. Burns once constructed a giant, movable disc designed to cast the entire town in shadow for 24 hours per day. In effect, the plan was to force Springfield to rely on his electricity rather than natural sunlight. 

The act proved to be the catalyst for the infamous "Who Shot Mr. Burns?" two-part mystery that saw the entire town outraged by Burns for one reason or another. The lack of sunlight was merely the straw that broke the camel's back, as earlier in the episode, the town turned on him after he tapped an oil well beneath Springfield Elementary, causing the school to lose funding and the town to be plagued by environmental disaster.

However, his sun-blocking plan was so bad that even Smithers broke rank and had to walk away from his life with Burns. And after announcing his nefarious plan to the entire town (who are now armed to the teeth), Burns might've thought he'd crossed the threshold from infamy to invincibility, but a swift shot from an unlikely townsperson put an end to that perception. Still, Burns blocking the sun remains among his most high-profile acts of villainy. It showed that he was okay with the entire town wanting him dead if it meant a few more bucks in his wallet.

He literally tried to take candy from a baby

In the "Who Shot Mr. Burns?" saga, it's eventually revealed that it wasn't Burns' grand villainous plan to block out Springfield's sun or even slant-tapping an oil reserve meant to benefit an elementary school that got him shot. Instead, it was an even more craven and petty act.

Mr. Burns straight-up tried to take candy from a baby.

The entire story sees Burns feeling more and more invincible and entitled to do whatever he pleased. And at one point, he notices little Maggie Simpson holding a delicious-looking lollipop. This is where Burns reaches the peak of his narcissism and simply decides to snatch the candy for himself, unaware that his pistol was precariously placed in its holster. In the old man's struggle with the baby, the gun falls and goes off into his chest, giving him some much-needed comeuppance for trying to do something so awful that it's used as a metaphor for doing something mean just because one can.  

In addition to humbling Burns, this moment also solidified Maggie as bit of a violent baby who would go on to shoot and/or maim many other characters as the show progressed. All the same, taking candy from a baby, for a time, marked the tipping point for how far Burns could go.

He gave a whole lot of money to an infamous dictator

In the episode "The Trouble with Trillions," it's revealed that after World War II, Harry Truman minted a one trillion-dollar bill in an effort to reconstruct post-war Europe. The U.S. government then tasked none other than a spry, young Mr. Burns with flying the money to Europe. However — surprise, surprise — it never arrived. (It's implied this is the reason Europeans are snooty to Americans.) Obviously, this alone has got to be one of Mr. Burns' worst acts, but wait, there's more.

It's revealed that Burns kept the money on his person for all these years. With that knowledge, the FBI bursts in to arrest him, but Burns manages escape by fleeing the country. With the help of Smithers, Burns decides to buy a tiny little island he found on a map. Unfortunately, that island happens to be Cuba, which some will note is kinda spoken for when it comes to land agreements. Armed with $1 trillion in cash, though, Burns is undeterred and presents the money to the country's dictator, Fidel Castro. Sadly, the world leader proves to be too cunning for Burns by asking to see the bill and then merely pretending it was never handed to him. 

With that, Burns ventures back to the states, defeated.

He's basically the Cruella de Vil of The Simpsons

Although this moment is responsible for one of the better toe-tappers in Simpsons history, it's also one of Burns' most evil acts to date — especially if you're an animal lover. 

When the Simpson family dog, Santa's Little Helper, gets frisky with a female racing dog, the family finds themselves the proud-yet-overwhelmed owners of 25 Greyhound puppies. Although they make a valiant effort to care for the dogs, they're forced to sell them. As they debate letting an oddly interested Burns take the whole litter, the devious tycoon steals them when their backs are turned.

Fortunately, Bart and Lisa track them down at Burns Manor and hear him sing his plans to make the dogs into a tuxedo. It turns out he's an avid fur collector, which again feels like enough of a villainous act to merit inclusion on this list. But in the now-legendary song "See My Vest," Burns lists off not only his plans to kill the 25 dogs, but he also admits to killing everything from a gorilla and an Irish Setter to poodles, robins, and an albino African endangered rhino.

He's serious about getting his new tuxedo, too. When Bart and Lisa intervene before he can slaughter the helpless puppies, Burns holds the fourth- and second-grader at gunpoint in order to stop them. Fortunately, Burns decides not to kill the dogs in the end and vows to never wear the fur of another animal ... that can do an amusing trick (sorry, gophers).

He harassed Marge

In the episode titled "Marge Gets a Job," Marge finds work at the nuclear power plant in order to supplement the family's income. Unfortunately, that's when her new boss, Mr. Burns, becomes completely enamored with her. He begins to court her in his own way around the office in an effort to seduce her into falling as in love with him. It's a great example of The Simpsons being ahead of its time and tackling something as complex as workplace power dynamics and sexual harassment. 

Things boil over when Burns essentially kidnaps Marge's favorite singer, Tom Jones, and invites her to a concert. Marge misconstrues the gift and notes that she's excited to take her husband. Realizing she's married, Burns fires Marge who, in turn, threatens to "sue the pants off" him. "You don't have to sue me to get my pants off," Burns retorts, along with a disgusting cat growl. The moment is especially gross in today's #MeToo world, but things eventually end on a high note, even for Burns.

After Homer confronts his boss to defend his wife's honor, the old-fashioned Burns realizes that at least the woman he loves has someone defending her with the same tenacity he would. In an act of contrition, he puts on a special Tom Jones concert for Homer and Marge. However, Burns never truly abandons his villainy, and it's worth noting that Jones performs against his will.

Mr. Burns is responsible for mass animal murder

This is a unique inclusion on the list because it marks a rare occasion in which Burns doesn't revel in his villainy. Instead, his bad behavior merely comes from a deeply misguided place. 

After a series of bad investments causes Burns to lose his vast fortune, the episode "The Old Man and the Lisa" sees him forced to live the life of an average Joe, even shacking up with Smithers for a brief period. However, his quest to find fulfillment as an impoverished elderly person is short-lived as his life quickly spirals out of control and lands him in the Retirement Castle. 

When Lisa Simpson comes around on a crusade to increase Springfield's recycling, Burns decides to mend his previously greedy ways by attempting to give back. It seems like things are going well as Lisa's desire to help the environment meshes with Burns' business acumen. However, upon the opening of the Little Lisa Recycling Plant, Burns reveals that he's strung together hundreds of plastic six-pack holders to "sweep the sea clean" of both waste and marine life. In a horrific, albeit well-animated, shot, viewers see hundreds of animals being dragged from the ocean and minced into an animal slurry that Burns then sells.

Lisa is obviously horrified, much to the confusion of Burns, who genuinely believes he merely took recycling to the next level. Although this is by far one of Burns' worst acts, it's scary to think that mass animal murder is him operating at his best intentions.

He tried to murder Homer Simpson

In the episode "C.E. D'oh," Homer learns that Mr. Burns has dumped toxic waste in Lego Land, causing the creations to come to life and attack patrons. The mogul isn't worried about legal ramifications because he reveals that the legal owner of the power plant is a canary with Burns' name. In a scheme that's surprisingly clever for the likes of Homer Simpson, he frees the canary and tells Burns that inspectors are on the way, prompting Burns to hastily appoint him as the new CEO. 

Burns is enraged by the coup and hatches a scheme of his own. So he takes Homer on a late-night trip to the cemetery where he shows him the Burns Family Mausoleum. After spending the entire episode learning how difficult and time-consuming it is to be the CEO of a large company, Homer is drained. Burns gives a speech about the time commitment and makes Homer think he'd be better off as a family man than a CEO. Homer is about to agree when Burns knocks him out and begins to wall him inside the mausoleum, brick-by-brick. 

Unfortunately, Burns is older and frailer than the villain in "The Cask of Amontillado" (the short story that made the wall gag famous). By the time the sun rises, he's barely got enough bricks laid to reach Homer's ankles.

Mr. Burns ditched his parents ... and possibly murdered them

By now, it's clear that Burns is capable of cartoonish levels of villainy (even for an animated bad guy). And you may be wondering, where did it all start? If a flashback in the episode "Rosebud" is to be believed, it was within Burns all along. 

In a dream, Burns recalls his happy childhood with loving parents who take terrific care of him. One day a, "twisted, loveless billionaire" arrives in a stretch limo and seemingly offers to purchase Burns. When his parents give him the option, they're barely finished talking before Burns is in the limo saying, "Let's roll." 

It's one of the few times Burns' parents are mentioned in the entirety of the series, and it shows that, even as a child, he was unkind, ungrateful, and out only for himself. His relationship to his parents is further complicated in the episode "The Mansion Family" when he goes in for a checkup and answers the form question "cause of parents' death" with "got in my way." 

As diehard Simpsons fans will note, Burns' parents have been referenced throughout the series on a rare occasion, and his mother was even proven to be alive at certain stages. So the line is more of a throwaway joke than hardcore canon.  Still, it's clear these two moments make it clear that Burns is tethered to no sentiment or love. He's an unstoppable negative force that Springfield and viewers love to hate.