So if you haven’t heard, Tom Waits was on The Simpsons last night, voicing “a gravelly voiced paranoiac” prepper and joining the long list of illustrious and not-so-illustrious guest stars who’ve graced the show since it started screening way back in 1989. His appearance got us thinking about some of the more unlikely guest stars and/or performances the show has seen over the years — and so we’ve amused ourselves after the jump selecting some of our favorites, from Johnny Cash playing a psychedelic coyote to Thomas Pynchon breaking a 40-year TV silence. Did we miss any of your favorites? Go ahead and let us know. (And advance apologies for the quality of a couple of the clips — Simpsons videos are like hen’s teeth on YouTube.)
Michael Jackson in “Stark Raving Dad,” Season 3
The original, and arguably still the strangest of the lot. This episode features Homer being sent to a mental institution, where he shares a cell with a heavyset white man who is convinced that he is Michael Jackson. The twist, of course, is that he really is Michael Jackson — or, at least, he’s voiced by the King of Pop himself. Apparently Jackson was a huge fan of the show, calling Matt Groening to offer his services and being closely involved with the scripting and production process.