Top 10 Cameos in ‘The Simpsons’ (Round 2)

Last week we looked at the cameos of characters playing themselves…now it’s time for the other side of the coin: actors playing other characters.

#10 – Eric Idle

Eric Idle Simpsons

Declan Desmond is the greatest asshole documentary film-maker ever. Whether it’s Do You Want Lies With That, American Boneheads or Springfield Up his condensing tone reflects his desire to put down his subjects for the viewer’s amusement. His polished tone is a clear parody of David Attenborough but his confrontation documentary technique is more akin to Michael Moore. He’s made a couple of appearances over the years and every single one gets a laugh.

#9 – George Takei

George Takei Simpsons

Oh, George Takei…you are a treasure. Every time he pops up in a cameo, or even an advertisement or on Facebook, it’s downright brilliant. He’s got a dynamic personality and manages to win everyone over. His flippant way of talking made him the perfect fit for Wink the Japanese game show host who torments the Simpsons family. He gets a place on the list just for this exchange:

Wink: “You must answer a question about Japan.”

Homer: “Is the answer ‘Japan’?”

Wink: “Actually it is.” Turns backstage and shouts angrily in Japanese.

#8 – Jon Lovitz

Jon Lovitz The Critic Artie Ziff

Jon Lovitz has actually played two roles in The Simpsons, one a recurring character and the other a cross-over from another series. Artie Ziff first featured in a flashback episode has Marge’s disrespectful prom date. Although his appearance are few and far between he does resurface from time to time making frequent attempts to win Marge over. Having become a self-made millionaire he has attempted to tempt both Marge and Homer with large offers of money. Lovitz also appears as Jay Sherman from the under-appreciated animated show The Critic, appearing as a guest film critic during Springfield’s first film festival.

#7 – Dustin Hoffman

Dustin Hoffman Mr. Bergstrom

Although he used a false name during the episode (leading to him and the #2 entry later becoming an in-joke for the ‘Itchy and Scratching Movie’) there was no mistaking Dustin Hoffman in the role of substitute teacher Mr. Bergstrom. It’s not often that we get such an effective episode based around Lisa, who’s feeling like she lacks any positive male role models. When Mr. Bergstrom takes over her class she finds an adult male who is unapologetically intelligent and sensitive. He’s very much the teacher that many children wish they’d had, as he instills Lisa with a stronger sense of self than anyone had before.

#6 – Patrick Stewart

Patrick Stewart Stonecutters

Almost an underplayed cameo as the focus of the episode is on Homer, with Patrick Stewart filling out a small supporting role. He brings the comedy gold to the small part of Number One regardless of how little he’s in the episode. The Stonecutters episode, in which Homer joins a secret society, is frequently listed as one of the best episodes and features Stewart as the sombre chapter leader. With his rich voice instructing his followers to paddle Homer’s butt and eat ribs the episode is full of classic moments. Now attach the stone of triumph!

#5 – David Duchovny and Gillian Anderson

Simpsons X-Files

Kinda toes the line this one, as the actors are playing the characters that they’re known for but this entry fits here more than the previous list. Mulder and Scully from The X-Files, a show that was a powerhouse when it first aired and was one of the most talked about shows of the 90s. Seeing them cross over into something so radically different as The Simpsons was a stroke of demented genius. When a highly inebriated Homer happens upon an alien being in the woods and although no-one believes him the FBI arrive to investigate. Duchovny and Anderson are clearly taking the piss out of their characters, but do it in such a dry manner that almost every joke hits the mark.

#4 – John Waters

John Waters Simpsons

Homosexuality is a topic that has been addressed a few times on The Simpsons in recent years, and Smithers has always been portrayed as a closeted character. When Homer met store owner John it represented one of the earliest instances of homosexuality and discrimination against them being directly addressed in the show. John and Homer became quick friends but when Marge points out to the oblivious Homer that John is very outwardly gay Homer decides that he doesn’t want to have anything to do with him, and even becomes paranoid that Bart is turning gay. It works out to be a more effective episode than the one when Selma gets married because it explores Homer’s unfounded prejudges in response to a man who is trying to be friendly and understanding. Also, this:

#3 – Johnny Cash

Simpsons Johnny Cash

Certainly the most surreal entry into this list. Whilst in attendance at a chili festival Homer over-indulges by swallowing several atomic level chilies. This results him going on a hallucinogenic journey lead by his spirit guide, a mystical coyote. This abstract and extremely well animated sequence is further enhanced by the famously deep and resonant tones of country rock singer Johnny Cash.

#2 – Michael Jackson

Michael Jackson Simpsons

In one of the oddest casting gags in the history of…well, history…Michael Jackson played mental health patient Leon Kompowsky, who was in the asylum because he though he was Michael Jackson. Some shows might’ve been happy to rest on that one gag but this being an early days The Simpsons they took things much further. Homer winds up sharing a cell with ‘Michael’ after wearing a pink shirt to work and being declared insane. Homer, unaware of who Michael Jackson really is, forms a close friendship with his cell-mate and decides to take Michael home to visit Springfield. Bart, expecting the real thing, whips the town up into a frenzy only for the bubble to burst when they come face to face with Leon. Bart is shattered until Michael composes a birthday song for Lisa after Bart had forgotten to get her a gift. Michael Jackson did compose and perform the song himself and it was later included on a The Simpsons compilation album.

#1 – Kelsey Grammer

Kelsey Grammer Sideshow Bob

Obviously the #1 choice. Kelsey Grammer first lent his distinctive tones to Sideshow Bob way back in the first season and has been a recurring and popular figure ever since. Sideshow Bob was originally a mute character just playing the foil to Krusty and Grammer came into the role in ‘Krusty Gets Busted’, when Bob framed Krusty for aimed robbery as revenge for his humiliation. Bart foiled this plan and many of his future appearances revolved around Bob trying to get revenge on Bart for sending him to jail. His schemes are elaborate and range from hunting Bart down with a machete to blowing up Springfield with an atomic bomb.

What makes Sideshow such a popular character is the juxtaposition between his murderous bent and his championing of high culture. He’s well-read, politically involved and rallies against ‘low’ culture such as television. The inspiration for the character is largely taken from Kelsey Grammer’s long running sitcom character Fraiser but driven to a psychotic extreme. His dark personality is balanced with some brilliant sight gags and slapstick, with the rake routine being a fan favourite (even though is was used just to fill out the time frame of the episode).

With Kelsey Grammer being willing reprise the role time and time again we’ve had the opportunity to see the character develop. Best of all was the introduction of Cecil, his younger brother, who set out to set revenge on Bob for stealing his dream of being a clown. Cecil was brilliantly played by David Hyde Pierce, who is best known as playing Frasier’s on screen brother with Kelsey Grammer. More than stunt casting, the dynamic between the two snobbish nutjobs was comedy gold.