The Simpsons is the longest running prime-time scripted show of all time. Although it’s perhaps no longer the classic TV it once was, throughout it’s golden age it produced countless memorable episodes that often-included unforgettable guest stars. Here at Boomslang we decided to countdown our Top 10 all-time best guest stars from the classic era of the show. Let us know if you agree with our picks!

10. Michelle Pfeiffer as Mindy Simmons

Season: 5

Episode: 7 – ‘The Last Temptation of Homer’

Homer becomes so attracted to the new employee at the plant, that it could spell disaster for his marriage to Marge. He soon discovers that they have so much in common, and he tries to avoid her. However, they go to a Nuclear Power Convention in Capital City together. Pfeiffer does an excellent job in this episode of staying likeable, bearing in mind it would be easy to hate the character for being ‘the other woman’ coming between Homer and Marge.

9. Mark Hamill as Himself

Season: 10

Episode: 9 – ‘Mayored to the Mob’

When Homer rescues Mark Hamill and Mayor Quimby from a brawl in a sci-fi convention, he is appointed the mayor’s new bodyguard. But after convincing Quimby that he needs to prevent Fat Tony’s mob from selling rats milk to the town’s schools, the mayor’s life is placed in jeopardy. A common theme in the success of The Simpsons guest stars is when the person can laugh at themselves. This is evident in Hamill’s performance, as he fully embraces his Star Wars past, as well as the good and bad sides of the fandom throughout.

8. Barry White as Himself

Season: 4

Episode: 12 – ‘Whacking Day’

Bart ruins a review of the school by Superintendent Chalmers by stealing Groundskeeper Willie’s tractor while trying to escape from detention. Principal Skinner is furious with Bart and expels him, forcing Marge to home school Bart. Meanwhile, everyone in Springfield is excited for Whacking Day, but as the holiday approaches, Lisa condemns it as violent. Whacking Day is a decades-long tradition which calls for the townspeople to beat snakes to death with sticks. Lisa plans to save the snakes with the help of Whacking Day’s honorary MC, Barry White, who uses his sonorous bass vocal style to lure the snakes to safety, where no one can whack them – ‘Don’t bother the snakes, leave allllll the snakes, alone’. Right on, Barry.

7. Dustin Hoffman as Mr. Bergstrom

Season: 2

Episode: 19 – ‘Lisa’s Substitute’

Dustin Hoffman–using the pseudonym Sam Etic–guest stars as Mr. Bergstrom. The episode features references to The Graduate, which starred Hoffman, and the novel Charlotte’s Web by E. B. White. This episode was also the first full appearance of Ralph Wiggum. When Lisa’s teacher Miss Hoover gets Lyme Disease, Mr. Bergstrom takes over the class. Lisa finds Mr. Bergstrom’s teaching methods incredibly inspiring and discovers an entirely new love for learning, but when Mr. Bergstrom leaves, Lisa doubts that anyone else in her life (including her own father) can be the man that Mr. Bergstrom was.

6. David Hyde Pierce as Cecil Terwilliger

Season: 8 – 21

Standout Episode: Season 8, Episode 16 – ‘Brother from Another Series’

Bart suspects a sinister motive when Sideshow Bob reunites with his estranged brother Cecil, who promptly places Bob in charge of supervising the building of Springfield’s Hydroelectric Dam. The Simpsons writers were smart to capitalise on the chemistry Hyde Pierce and Kelsey Grammer already shared on their show, Frasier. Essentially all you have here are animated Niles and Frasier Crane scenes, but they are all gold.

5. David Duchovny & Gillian Anderson as Fox Mulder & Dana Scully

Season: 8

Episode: 10 – ‘The Springfield Files’

Homer sees an alien in the woods near Springfield, but no one believes him, not even FBI Agents Mulder and Scully, who come to investigate the incident. Leonard Nimoy begins the episode hosting a show about alien encounters. He begins talking about an encounter in a town called Springfield. At Moe’s on Friday night, Homer drinks over ten bottles of “Red Tick Beer”, a brand that is brewed with real dogs. He takes a breathalyser test which declares he is as drunk as Boris Yeltsin, so he decides to walk home. However, Homer takes the wrong path and ends up lost and disoriented in the woods. In a clearing, he sees a glowing thin-boned alien. Duchovny and Anderson are great in this classic episode, fully embracing the silliness of the plot and joyfully hamming up their roles as the famous FBI agents.

4. Danny DeVito as Herbert Powell

Seasons: 2 – 24

Standout Episode: 15 – ‘Oh Brother, Where Art Thou?’

Fearing death, Grandpa Simpson tells Homer that he has a half-brother. This half-brother, Herbert Powell, is a millionaire car manufacturer in Detroit, and wants Homer to design a car for the average man to save his car company. DeVito is perfect as ‘Unky Herb’. His emotional range is in full show throughout this classic episode, from genuine love for his newfound family, to his rage at the unveiling of ‘The Homer’.

3. Johnny Cash as Space Coyote

Season: 8

Episode: 9 – ‘The Mysterious Voyage of Homer’

After Homer downs several Guatemalan insanity peppers at the annual chili cook off, his consciousness goes on a mystical journey, complete with a talking coyote spirit guide, to discover his soul mate. It’s still crazy to me that Cash agreed to do this, but it just goes to show how popular and influential the show was at the height of its powers. Cash’s performance is brilliant though, as he gets to deliver both genuinely funny and poignant lines throughout – “I speak of a deeper wisdom. The problem, Homer, is that the mind is always chattering away with a thousand thoughts at once.”  

2. Michael Jackson as Leon Kompowsky

Season: 3

Episode: 1 – ‘Stark Raving Dad’

Thanks to Bart leaving his lucky red hat in the pile of washed white shirts, Homer wears a pink shirt to the nuclear power plant. He is promptly committed to a mental institution where he meets with a heavy-set, bald man, Leon Kompowsky, who walks and talks like Michael Jackson. The other theme of the episode is that Bart doesn’t understand what to get for Lisa’s birthday. Michael Jackson himself voiced Leon Kompowsky’s dialogue, but it was actually sound-a-like Kipp Lennon that performed all the singing parts! This episode offered a rare insight into Jackson’s sense of humour, particularly that he could make jokes about his own fame and persona.

1. Kelsey Grammer as Sideshow Bob Terwilliger

Season: 1 – 27

Standout Episode: Season 5, Episode 2 – ‘Cape Fear’

After Bart starts receiving death threats from his old nemesis, Sideshow Bob, the Simpsons enter the Witness Relocation Program and move to Terror Lake, a “Cape Fear”-esque town several miles away from Springfield. Bob has appeared in some absolute classics over the years, but this episode must be the stand out. It was the last episode produced by the show’s original team of writers, most of whom subsequently left. Even when they were struggling to meet the episode’s running time and created a joke just to fill some time, they came up with the gold that is the rake gag.

Do you agree with our picks? Was your favourite not in our list? Let us know!

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