The Most Excellently Evil Mr. Burns Moments In The History Of ‘The Simpsons’

The season 28 premiere of The Simpsons (which airs Sunday, September 25) will be the show’s 597th (!) episode. According to the plot description, Springfield is burned to the ground and “the Simpsons beg Mr. Burns to fund its rebuilding. Burns agrees with one condition: He gets to put on a variety show at the Springfield Bowl.” What could go wrong? Everything. It’s Charles Montgomery Burns after all, a man who laughed for hours, if not days, over the memory of crippling an Irishman. He’s “pure evil,” said voice actor Harry Shearer, who called Burns his favorite character in an interview with The Jewish Chronicle. “A lot of evil people make the mistake of diluting it. Never adulterate your evil.” With that in mind — and in honor of the premiere and that crippled Irishman — here are Mr. Burns’ most villainous moments.

7. “Bart Gets Hit By a Car” (1991)

Mr. Burns appears in the premiere episode of The Simpsons, but he didn’t get his first real showcase until season two’s “Two Cars in Every Garage and Three Eyes on Every Fish,” where he comes across as more unpleasant than downright evil. That all changed in “Bart Gets Hit by a Car.” Bart is skateboarding around Springfield when he — um, thanks for the spoiler alert, episode title — gets hit by a car driven by Mr. Burns. Smithers immediately comes to the boy’s attention, considering he’s knocked out in the middle of the street, but Mr. Burns is mostly annoyed that Bart had the gall to collide into him. “Just give him a nickel and let’s get going,” he tells Smithers. Meanwhile, Bart’s spirit is hanging out in Hell with the Devil himself, who, shockingly, doesn’t look like Mr. Burns. It took Bart nearly dying for a villain to be born.

6. “The Old Man and the Lisa” (1997)

Lisa thinks she’s changed Mr. Burns for the better after he loses all his money. Poor gullible Lisa, always seeing the best in the worst. Mr. Burns, who she calls “the worst man in the world,” takes all the things he taught her — recycling, a penny saved is a penny earned, only do “socially responsible things,” nothing evil — and turns it into Li’l Lisa’s Patented Animal Slurry. In possibly the most disgusting scene in Simpsons history, a bevy of sea creatures, including whales, dolphins, and “a million fish,” are liquefied into a horrifying goo. Mr. Burns regains his fortune, and offers Lisa 10 percent of $120 million, which Homer mistakenly believes is $12,000. When he learns how much it actually is, well, let’s just say Homer won’t be putting any catsup (ketchup?) on his hamburgers after all the heart attacks he has.

5. “Marge Gets a Job” (1992)

In “Burns, Baby Burns,” the episode where Mr. Burns’ long-lost son returns, the Simpsons tell Larry (the son) how they know his father. Lisa: “He tried to kill our puppies.” Grandpa: “He stole my fiancée.” Homer: “He made fun of my weight.” Marge: “He sexually harassed me.” Marge is referring to an incident where Mr. Burns developed a crush on her after she starts working at the Springfield Nuclear Power Plant. When she rebuffs his ancient advances, Marge is canned. “You can’t fire me just because I’m married,” she tells Mr. Burns. “I’m going to sue the pants off you.” He responds, with a purr and a growl, “You don’t have to sue me to get my pants off.” Who could resist that?

4. “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish'” (1996)

According to Frinkiac, the greatest website in the history of the internet, “Nazis” has only been uttered on The Simpsons four times. Unsurprisingly, it’s Mr. Burns who says the word twice: in season six’s “A Star Is Burns,” where he reveals he made shells for the Nazis (“But mine worked, dammit!”) and again in season seven’s “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish.'” During World War II, Mr. Burns and Grandpa were in the same infantry squad, the Flying Hellfish, and after discovering several priceless paintings in a German castle, they, along with Chief Wiggum, Principal Skinner, and Barney’s fathers, agree to a tontine. Whoever dies last gets the artwork. Despite already being as rich as a Nazi, Mr. Burns stops at nothing to make sure he’s the final Flying Hellfish, including hiring the world’s most devious assassin to murder Grandpa, and nearly killing Bart by threatening to shoot him then trapping him in a vault that sinks to the bottom of a lake. It’s not about the money for Mr. Burns — it’s about winning, and that’s what makes him a classic villain. (It’s somewhat about the money, too.)

3. “Who Shot Mr. Burns?” (1995)

There’s evil, and there’s evil. Evil is hiring a human prank monkey and instructing him to throw pudding at Lenny’s eye (not Lenny!). Evil is establishing a slant drilling operation to steal oil and money from an elementary school and blocking out the sun so Springfield will be forced to use electricity from the Power Plant. The two-part “Who Shot Mr. Burns?” is arguably the most famous installment(s) of The Simpsons — even people who didn’t watch the show before the episode, and haven’t watched since, are aware of it. Part one ends with Mr. Burns collapsing on a sundial with a bullet in his chest; part two picks up with the Springfield police searching for who pulled the trigger. Everyone in town is a suspect, because everyone has a reason to want Mr. Burns dead. Even baby Maggie. Do not try to steal her lollipop. That’s evil.

2. “C.E.D’oh” (2003)

“C.E.D’oh” isn’t as well known as the other episodes on this list, but Mr. Burns still does something remarkably evil. After exposing the real owner of the power plant, a bird named Canary M. Burns (don’t ask), Homer tricks Mr. Burns into letting him become the new nuclear proprietor. It’s a short-sighted idea, because it means Homer has to, y’know, actually work, and he becomes depressed after having to lay off his friends and not see his family. He agrees to give the plant back, but not before Mr. Burns drugs and tries to permanently seal him in a crypt, brick by brick. Homer wakes up before the deal is done, but it’s still dastardly.

1. “Two Dozen and One Greyhounds” (1995)

Take it away, Mr. Burns.

I suppose nearly shooting Bart, or trapping Homer in a crypt, or sexually harassing Marge, or literally blocking out the son is objectively worse than murdering dogs to make a greyhound tuxedo, but nope. This — along with his Irish setter sweater, gorilla chest vest, and grizzly bear underwear — is the worst thing Mr. Burns’ ever done. If only the song wasn’t so damn catchy.