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Jackie Mason won an Emmy for playing Rabbi Hyman Krustofski, aka Krusty the Clown's father, on the episode "Like Father, Like Clown."
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Maude Flanders died on a 2000 episode of the show, but still makes the occasional posthumous appearance.
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Lisa's sax-wielding mentor Bleeding Gums Murphy is one of the first recurring characters "The Simpsons" killed off.
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Jebediah Springfield died well over a hundred years before Homer Simpson was born, but he's the town's namesake and the star of several episodes.
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Poochie died on his way back to his home planet in 1997.
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The Gypsy appeared on several episodes of "The Simpsons," once turning Lisa into a Centaur, but died while reading Abe Simpson's fortune.
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Grimey died in an accident at the nuclear power plant while trying to prove Homer's idiocy.
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Mob boss "Fat Tony," voiced by Joe Mantegna and at one time Phil Hartman, had a heart attack and died while in Homer's arms.
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Dr. Marvin Monroe was pronounced dead on the show's 138th episode spectacular and even got a tombstone in Springfield Cemetery, but reappeared nearly 10 years later explaining he'd "been very sick."
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The submarine captain torpedoed himself into an enemy ship in "Simpson Tide" and is presumed dead
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Arnie Gumble was killed off on his one and only episode, "The Curse of the Flying Hellfish"; he served alongside Abe Simpson memorably.
