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

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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.

Buzz Aldrin in “Deep Space Homer,” Season 5

Always a good sport, Aldrin proved again that he had a sense of humor with this appearance. It’s James Taylor’s guest performance in this episode that usually wins the plaudits, but Aldrin’s has a certain earnest charm that only makes the whole thing more amusingly bizarre. (Also, if you’ve ever wondered where the “And I for one welcome our new [insert name] overlords” line comes from, look no further.)

Winona Ryder in “Lisa’s Rival,” Season 6

Full disclosure: this is your correspondent’s all-time favorite Simpsons episode, featuring a genius plot built around Edgar Allan Poe’s The Tell-Tale Heart, a glorious Homer soliloquy (“the terrifying lows, the dizzying highs, the creamy middles!”), Ralph Wiggum’s single best line (“I bent my wookie…”), and to cap it all, an excellent cameo from the then squeaky-clean Winona Ryder as the rival of the title, a new girl at school who turns out to be just as bright and precocious as Lisa is. When The Simpsons was at its best, it was pretty much untouchable.

John Waters in “Homer’s Phobia,” Season 8

One of the strengths of The Simpsons‘ glory days was the show’s ability to take on serious “issues” with equal measures of wit and surprising seriousness. So it went with this episode, in which Homer worries about the influence of new family friend “John” on Bart’s sexuality. Waters reveled in the role and played it beautifully, although in a depressing example of life imitating art, Fox’s censors originally refused to clear the episode because of its “controversial” subject matter. Extra points for the pun-tastic episode title.

Johnny Cash in “El Viaje Misterioso de Nuestro Jomer,” Season 8

Another of the all-time great Simpsons episodes, this finds Homer eating the world’s hottest chili pepper and, as a result, embarking on a gloriously tripped-out psychedelic odyssey under the guidance of a spiritually enlightened coyote. As if the whole thing weren’t awesomely strange enough already, Homer’s spirit guide is voiced by none other than the Man in Black, Johnny Cash.

Rupert Murdoch in “Sunday, Cruddy Sunday,” Season 10

Hey, the Antichrist guy who owns Fox was on The Simpsons! Who’d have thought it?! We’d be interested to know what he made of the dig that the show took at Fox News last year, though.

Stephen Hawking in “They Saved Lisa’s Brain,” Season 10

Your correspondent’s long-lost relative (hey, don’t laugh, it might actually be true) has appeared on The Simpsons three times to date, starting with the above episode. There’s some fascinating stuff on Wikipedia about his appearances, especially the fact that although it would have been easy to create his lines from any computer with voice synthesis capabilities, Hawking insisted on recording them himself, typing them painstakingly into the custom-made computer he uses to communicate with the world. (Sadly, the real-life version doesn’t have a built-in boxing glove for clobbering barroom miscreants.)

Mel Gibson in “Beyond Blunderdome,” Season 11

Back when Mel Gibson was best known for Mad Max and Braveheart — as opposed to for being the violent alcoholic anti-Semitic ball of fun we know today — he moonlighted as himself on The Simpsons in a somewhat heavy-handed Hollywood parody. There’s plenty of existential irony in the clip above — the best bit, though, came when the show’s writers conceived a scene wherein Gibson confesses to urinating in a dumpster, the joke being that no real Hollywood star would do such a thing. Except, um, Gibson had. Oops.

Thomas Pynchon in “Diatribe of a Mad Housewife,” Season 15

We still can’t quite believe that this actually happened. After all, we’re talking about a man who’s never been interviewed on celluloid or in print, never been photographed, and generally made JD Salinger look like a gregarious outgoing kinda dude. He was (and remains) so reclusive that before this episode, no one really knew what his voice sounded like. And what does it sound like? Click play above and all will be revealed.

Matt Groening in “My Big Fat Geek Wedding,” Season 15

In which Groening appears in his own show, appearing at a sci-fi convention as… the creator of Futurama. Oh, the meta-ness of it all! (The fact that his appearance coincided with a strike by the show’s voice actors is, we’re sure, entirely coincidental.)

Ted Nugent in “I Don’t Wanna Know Why the Caged Bird Sings,” Season 19

The fact that the Nuge has been prepared to appear on the Simpsons not once but twice — each time in episodes that poke fun at his gun-totin’, meat-eatin’ ways — is further fuel for the theory that the man isn’t quite as crazy as he likes to make out. Apart from the above episode, he also appeared in a newer one called “Politically Inept, with Homer Simpson,” in which Homer hosts a right-wing TV show and chooses the Nuge as a Republican presidential candidate, an obviously outlandish scenario which could never happen in… um, yeah, anyway.

Julian Assange in “At Long Last Leave,” Season 23

The benefit of guest starring in a cartoon: you can record your lines from your room at the Ecuadorian embassy in London!