First appearance: “Homer’s Enemy” (Season 8, Episode 23)
Voiced by: Hank Azaria

Frank Grimes may only show up in one Simpsons episode, but it's one of the best the series has to offer. The episode in question? “Homer’s Enemy,” which revolves around what happens when Grimes, an average hardworking Joe from the real world, gets dropped into Springfield and has to be co-workers with Homer at the nuclear plant. Grimes’ good-natured, industrious personality is quickly put to the test as he has numerous run-ins with Homer, his polar opposite.

Within the span of this dark and twisted story, Homer breaks Grimes down to the point of insanity, and we as an audience are left to wonder why it is that we actually love this dangerous oaf so much in the first place.

In the end, Frank Grimes was just an ordinary man who wound up letting the absurd nature of Springfield lead him to an early grave. Grimes’ life can be viewed as a tragedy, but as the show has taught us over the years, the line between the tragic and the comic is as thin as the hairs on Homer’s head.