Every Death In The Simpsons Ranked
8. Fat Tony (Donnie Fatso)
In perhaps the most frustrating death on this list, Season 22's "Donnie Fatso" was a real opportunity for The Simpsons to change things up.
This episode revolves around Homer going undercover in Fat Tony's gang, eventually gaining his trust and friendship until his lies are uncovered when the FBI attempt to arrest the mob boss. Distraught by his new friend's betrayal, Fat Tony suffers a heart attack and dies in a conflicted Homer's arms.
Fat Tony had been a part of the show for almost 20 years at this point and had provided fans with a bounty of iconic lines and moments. As devastating as his death was, it was also exciting as a show famous for its status quo was changing it in a big way. At least, they did for about fifteen minutes...
By episode's end, Fat Tony's cousin "Fit Tony" is running the mob and the stress of the job causes him to put on weight, rendering him identical to his deceased cousin. He also assumes the moniker of "Fat Tony", basically making this whole episode pointless. Still, the original death was so surprising that it earns its place this high up the list.