The All-Time Weirdest Guest Appearances on ‘The Simpsons’

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.