Jackie Mason won an Emmy for playing Rabbi Hyman Krustofski, aka Krusty the Clown’s father, on the episode “Like Father, Like Clown.”
Maude Flanders died on a 2000 episode of the show, but still makes the occasional posthumous appearance.
Lisa’s sax-wielding mentor Bleeding Gums Murphy is one of the first recurring characters “The Simpsons” killed off.
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.
Poochie died on his way back to his home planet in 1997.
The Gypsy appeared on several episodes of “The Simpsons,” once turning Lisa into a Centaur, but died while reading Abe Simpson’s fortune.
Grimey died in an accident at the nuclear power plant while trying to prove Homer’s idiocy.
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.
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.”
The submarine captain torpedoed himself into an enemy ship in “Simpson Tide” and is presumed dead
Arnie Gumble was killed off on his one and only episode, “The Curse of the Flying Hellfish”; he served alongside Abe Simpson memorably.