#3. Joey Joe-Joe Junior Shabadoo (“The Last Temptation of Homer”)
Joey Joe-Joe Junior Shabadoo is funny in the same way that the words “Walla Walla,” “Keokuk,” “Cucamonga,” and “Seattle” are: they’re just fun to say. Homer is telling a purely hypothetical story at Moe’s about having romantic feelings for a co-worker, and he uses the fake name Joe-Joe Junior Shabadoo. Moe comments, “That’s the worst name I’ve ever heard,” and a man runs out of the bar crying. Barney shouts after him, “Hey, Joey Joe-Joe!” He was never heard from again.
#2. Roy (“The Itchy & Scratchy & Poochie Show”)
Roy, a Fonzie for the 1990s, was added to “The Simpsons” as a previously unseen, unknown houseguest to Mr. and Mrs. S after Fox executives told the show’s writing staff that they should add a new, hip character. Roy only has two lines of dialogue in the episode, yet he’s the perfect, meta parody of a show’s desperation on trying to “appear” cool, thanks to meddling from the Powers That Be. What’s become of Roy we’ll never know, but something tells me he’s still living with his two sexy ladies. Maybe we’ll see him again in a few years.
#1. Frank Grimes (“Homer’s Enemy”)
Before you get all “skeleton key in the wizard’s dungeon” on me, know that Frank Grimes himself has appeared in only one episode; his tombstone and his son make the other appearances. When “Homer’s Enemy” (written by the brilliant John Swartzwelder) aired in 1997, it stirred up a lot of debate among “Simpsons” fans on whether it was terrible or brilliant. The correct answer is, of course, brilliant, because as writer Josh Weinstein once said, “It really feels like what would happen if a real, somewhat humorless human had to deal with Homer.” It’s the show least “cartoon” episode, because Grimey, who had to teach himself to hear and feel pain again, was a surrogate for the audience—Homer’s fun to laugh at, because you don’t know him or have to deal with him, but what if you did? Frank Grimes did, and he died because of it.
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