Every Death In The Simpsons Ranked
13. Max The Ice Cream Man (Ice Cream of Margie (With The Light Blue Hair))
Homer starts off this Season 18 romp being chastised by Mr. Burns when an ice-cream truck passes the power plant. Unable to contain his desire for the sugary treat, Homer runs off and Burns fires him on the spot. Homer catches up with the truck and talks to its owner, an old man named Max. Max and Homer are good pals - seemingly through years of the latter keeping the former in business - but it Max's friendship with the big yellow oaf that is ultimately his undoing.
Homer uses a $100 bill to pay for a 25c ice cream (in 2006? not likely) and counting all of the change causes Max to have a fatal heart attack. Homer attends Max's funeral - which actually contains some pretty funny ice cream jokes - and buys the truck from his widow, also setting this episode's main plot in motion.
Max and Red Barclay die in very similar ways to each other, so they really could have been interchangeable on this list. However, for the ice cream jokes alone, Max gets the cherry on the top of the morbid sundae in our opinion.