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.