The Simpsons: 20 Most Shocking Moments Ever

By Sam Hill /

4. Death Of Frank Grimes - "Homer's Enemy" (8.23)

"Homer's Enemy" essentially set the stage for a plotline that begged the question: "What would happen if a person from the real world came to Springfield?" They'd end up insane and dead, apparently. Grimey's death, which sees him electrocuted during an ill-judged attempt to impersonate Homer, proved unexpected and shocking because it was so dark in both set-up and execution. Whilst it was deemed a step too far by some fans (the first sign of the show's decline into mean-spiritness), others thought it was super hilarious.