20. Death Of Bleeding Gums Murphy - "'Round Springfield" (6.11)
Once upon a time, The Simpsons could be as sad as it was funny; there's no better proof of that than "'Round Springfield," in which Lisa's hero, Bleeding Gums Murphy, dies unexpectedly. Shocking and upsetting in equal measure, this episode marks one of the most memorable deaths featured on the show, given that - at this point - fans weren't even sure whether or not Simpsons characters could be "killed off."