The Most Bizarre Simpsons Cameos In History

Over the past 30 years, The Simpsons has churned out memorable guest star appearances that fans eat up like frosty chocolate milkshakes. After all, famous people have always been more than willing to spend a couple of hours in a recording studio and voice a resident or two of the always growing city of Springfield. And in some cases, they've been willing to play a character based on themselves, throwing a little self-deprecating humor into the mix. 

Anybody who's anybody has guest-starred on The Simpsons at this point, and with more than 600 episodes in the can and counting, producers have had to dig a little bit deeper than the most obvious movie stars, musicians, athletes, and public figures. A remarkable cross section of artists, politicians, scientists, authors, broadcasters, and every other conceivable profession have made the rite of passage of voicing "themselves" on an episode of The Simpsons. However, some of these appearances are a bit weirder from others, if not completely baffling. From showrunners to literary authors, here are the most bizarre cameos in Simpsons history.

Even a casual fan of The Simpsons is familiar with the name Matt Groening, as he's the creator and executive producer of the extremely long-running animated series. By virtue of bringing one of the most popular and enduring TV shows of all time to the air, he's part of the cultural fabric of America, which makes him a viable candidate for a cameo appearance on The Simpsons. But how could the series do that? The world of the show would turn upside down and inside out if its characters came face to face with their inventor. 

But Simpsons writers are clever, and they've brought Groening into the show more than a dozen times. In 2004's "My Big Fat Geek Wedding," for example, the Simpson family is on the lookout for Comic Book Guy, and so they hit up the Springfield Bi-Mon-Sci-Fi-Con. Groening is there signing autographs ... because he's the famous creator of Futurama.

"The Regina Monologues" is a travel episode of The Simpsons, and this time, as Homer loves to proclaim, the Simpsons are going to England. Ostensibly, it's so Grampa can reunite with his World War II-era lost love, but the show is really about teasing British institutions and making the Simpsons look like "ugly Americans." Upon their arrival at Heathrow Airport in London, they're immediately welcomed by Prime Minister Tony Blair, who, at the time, was the sitting leader of the United Kingdom. 

Lisa is thrilled, while Bart is confused, wondering why Blair would stoop to "greeting lowlifes like us at the airport." The prime minister explains that he wants to "encourage all the world" to visit beautiful Britain. After he refuses Homer's offer of an American dollar to go away (but takes the dollar anyway), he recommends some tourist attractions before excusing himself to meet a Dutch couple at a different gate. To the strains of some brassy music out of a James Bond movie, Blair rockets away with a jet pack in a very James Bond fashion. Nevertheless, Homer thinks he's just met a different English pop culture icon, exclaiming, "Wow, I can't believe we met Mr. Bean!"

The Simpsons is one of the few shows that tackles the potentially risky subject of religion. Sometimes the show respectfully explores the nature of faith, and sometimes it satirizes belief. In the 2018 episode "Bart's Not Dead," things definitely lean in the satirical direction. Bart Simpson suffers an accident and makes up a story about visiting Heaven. His story spreads, and the producers of faith-based films want to make his experience into a movie. This includes a casting process, resulting in the very weird situation of performers playing themselves playing the Simpson family. 

Bones star Emily Deschanel wants to play Marge, Jonathan Groff from Glee and Mindhunter is keen to play Bart, and Wonder Woman herself, Gal Gadot, is up for the role of Lisa. At the end of the episode, there's a flash-forward, and a dead Bart heads to Heaven, adjacent to Jewish Heaven, where Gadot is hanging out. She isn't dead. As she explains, it's just that, "They like me so much I get to visit."

Apart from acting in cartoon series like The Simpsons, the other place where individuals can reach millions with just their voice is by hosting a radio show. And many of the most famous names in the radio game come from coast-to-coast National Public Radio (NPR). But while NPR's audiences are sizable, it's still just a small portion of the population that regularly tunes in to its thoughtful and low-key programming. So it's kinda weird that The Simpsons has put the rich yet calming voices of on-air personalities associated with the service to good use on several occasions. 

For example, Lisa, unsurprisingly a fan of NPR's progressive-leaning content, listens to Ira Glass on This American Life on "Elementary School Musical." The voice of Fresh Air's Terry Gross can be heard coming out of radios in "The Debarted" and "The Girl on the Bus," and All Songs Considered's Bob Boilen appears in a physical form in the 2016 episode "Gal of Constant Sorrow."

Certainly the most entertaining NPR moment, at least for fans of the current events game show Wait Wait ... Don't Tell Me!, arrived in the 2014 episode "Pay Pal." Lisa and a friend listen to the show, and hosts Peter Sagal and Carl Kasell play themselves. The contestant wins the show's quirky prize — Kasell will record their outgoing phone message, which he threateningly notes is "not optional."

It's not all that strange for hugely popular music stars to drop by The Simpsons. Michael Jackson popped up in an early episode, and all three then-surviving Beatles also stopped by, as have James Brown, Barry White, Tom Jones, Justin Bieber, Lady Gaga, and Britney Spears, among dozens of others.

Katy Perry has guest starred on the series, too, and while that's not in and of itself weird, the manner in which Perry appeared certainly is. She's the first person to ever play herself in live-action form on The Simpsons. In a segment of the 2010 "Treehouse of Horror"-esque anthology episode "The Fight Before Christmas," Maggie falls asleep watching a Muppets-like video and dreams that her regular cartoon world is a puppet world. The puppet Simpsons gets ready to leave for Hawaii, and puppet Moe comes over to house-sit, bringing along his (much taller) girlfriend, pop sensation Perry. In a very meta move, Perry wears a dress covered in pictures of the (cartoon) Simpsons family.

Will Shortz and the late Merl Reagle aren't extremely famous on the whole, but they're idols worthy of Beatlemania-esque screaming and fainting to a certain, relatively small segment of the population — hardcore crossword puzzle enthusiasts. Shortz and Reagle are among the most respected and well-known crafters and developers of high-level crossword puzzles, often laced with secret codes or humorous clues. And they were the right guys for the job on the 2008 The Simpsons episode "Homer and Lisa Exchange Cross Words," in which smartypants Lisa starts competing in and winning crossword puzzling tournaments. Homer upsets her after he's caught betting on her contests, and he tries to make amends by hiring the New York Times puzzle-making team, Shortz and Reagle, to make a special crossword that reveals a hidden apology. Lisa gets to meet her heroes and solve the bespoke puzzle, which Reagle himself constructed for the episode.

The Simpsons aired a special Irish-themed episode for St. Patrick's Day in 2009, with "In the Name of the Grandfather" sending the family overseas so that Grampa can enjoy his favorite pub in Ireland one last time. While Homer and his father attend to various beer-related matters, Marge and the Simpson kids go sight-seeing in the town of Dunkilderry until they run out of things to do. A shaggy looking busker overhears them and tells them that "there's always something to do in Ireland," and that he's "trying to woo back a girl [he] met in a music shop." He launches into a beautiful love song, only to be interrupted by a woman — the lady in question — yelling from a second-story window. "Leave me alone, I have a husband!" she implores. "And quit sending her pianos!" adds the husband, who pushes one out the window, smashing it to bits on the street.

It's a funny sequence, but one that's a lot more fun for viewers familiar with the 2007 indie movie Once. The busker is voiced by Glen Hansard, who played a Dublin musician in the film, and he sings "Falling Slowly," which won the Academy Award for Best Original Song. Hansard's co-star and co-songwriter, Marketa Irglova plays the married woman gifted a piano, slyly mirroring the plot of the film.

The Baha Men are perhaps the definitive one-hit wonder, known primarily but widely for the 2000 earworm of a novelty hit "Who Let the Dogs Out." However, the group has showed that it can make fun of itself, and that its members are okay with their place in the musical universe as the purveyors of an indefatigable guilty pleasure now heard primarily at sporting events to pump up crowds. See, despite just the one smash hit, the Baha Men have cameoed on The Simpsons twice. Curiously, both times were audio-only appearances. 

In the 2002 episode "Large Marge," Marge grooves in her car to Radio Disney ("The songs you love rewritten for babies!"), which plays the Baha Men remaking their dog song into "Who Left the Milk Out." While actual baby Maggie hates it, Marge loves it. "That's good satire," she says. "It doesn't hurt anyone!" The voices of the Baha Men return later in the episode, which finds Marge accidentally receiving breast implants. After she has them surgically removed, the band sings "Who Let Her Jugs Out." Remarkably, the Baha Men gave The Simpsons a third parody of its hit in the 2005 episode "Thank God It's Doomsday." Bart and Lisa go to a cool kids' hair salon, which blares, "Who Wants a Haircut."

Despite taking on as their profession the task of designing beautiful, functional buildings that most everyone in the world uses, not too many architects are household names. There's Frank Lloyd Wright and maybe Frank Gehry, but that's pushing it. So, if an architect absolutely had to show up on The Simpsons, it would have to be Gehry (as Wright died in 1959). 

The Toronto-born, Pritzker Prize-winning contemporary architect has built many unique and dazzling buildings, but when the 2005 episode "The Seven-Beer Snitch" first aired, he was best known for devising the Walt Disney Concert Hall (WDCH) in Los Angeles. Marge, on behalf of Springfield, asks Gehry to design it a similar building, and he rejects the offer, balling up the request letter and tossing it on the ground. Gehry then spots the visually pleasing wad of trash, which he turns into a design for the (WDCH-esque) Springfield Concert Hall. The bullies wind up using it as a skate park, so Gehry threatens to call their mothers. And that prompts Jimbo to taunt back with, "Yo, Frank Gehry, like curvilinear forms much?"

Amy Tan is one of America's most acclaimed living novelists, and her name is certainly well-known to avid readers or those who follow the bestseller lists. But the author of sensitive and moving works about the Asian-American experience like The Joy Luck Club and The Bonesetter's Daughter isn't the most likely person to put in a cameo appearance on a broadly funny primetime cartoon like The Simpsons. And yet, Tan showed up on the series, proved she had some comedic chops, and even got to knock pretentious, self-satisfied Lisa Simpson down a peg.

In the 2000 episode "Insane Clown Poppy," the Simpsons attend the Springfield Festival of Books at Lisa's behest. During an author panel, Lisa tells Tan how much he enjoyed The Joy Luck Club. "It really showed me how the mother-daughter bond can triumph over adversity," Lisa says, delivering a succinct assessment of Tan's best-known work. The author won't have it. "No, that's not what I meant at all," Tan admonishes. "You couldn't have gotten it more wrong."

On the occasional literary episode, real-life writers have turned in cameos in The Simpsons. In 2006's "Moe'N'a Lisa," bartender Moe gets his dark and sad poetry published, and he briefly becomes the toast of the literati, meeting greats like Gore Vidal and Tom Wolfe. Those two are relatively recognizable for their signature style (like Wolfe's white suit) and many talk show appearances over the decades. But the strangest writer cameo in Simpsons history came courtesy of Thomas Pynchon — the extremely reclusive author who didn't make a public appearance for decades. 

In keeping with his quest for privacy while also making fun of it, Simpsons animators rendered Pynchon (who voiced himself) as a guy with a paper bag over his head, upon which a large question mark has been drawn. While the bagged writer of The Crying of Lot 49 and Gravity's Rainbow made a background appearance in "Moe'N'a Lisa," he praised Marge's romance novel in 2004's "Diatribe of a Mad Housewife," and that same year, he ate a chicken wing in "All's Fair in Oven War."

The 2013 Simpsons episode "Dark Knight Court" satirizes and gently mocks the American court system, and yet it also features a cameo from an extremely prominent real-life defender of America's laws. During an Easter celebration, the Springfield Elementary band plays, only for Easter eggs to shoot out of their instruments and onto the crowd. Bart is falsely accused of committing the prank, and Lisa agrees to defend him, only she's unable to find a judge willing to give the consistently mischievous Bart a fair shake. 

That's when Grampa claims to have once met Janet Reno, which the kids believe is another of his tall tales. But he's telling the truth, and Reno shows up to preside over Bart's trial. Reno, a Florida state's attorney, was appointed attorney general in 1993 by President Bill Clinton and served until 2001. When Reno was offered the chance to voice herself on The Simpsons, she was suffering from advanced symptoms of Parkinson's disease, which can make speech difficult. Her sister, Maggy Hurchalla, told producers that Reno couldn't take the part. But noticing how similar the sisters sounded, show reps proposed that Reno and Hurchalla split the role. Reno was able to handle the one-liners, while Hurchalla took on the more sizable chunks of dialogue.