15 Best Guest Voices Of The Simpsons’ Golden Era

While the cast of The Simpsons has been populated by some of the most talented voice actors for 25 years now, the show wouldn’t be what it is today hadn’t it been for the guest appearances of some of the most talented actors, comedians and musicians in the entertainment landscape.

By Justin Sedgwick

Updated 11 years ago, February 6, 2014

While the cast of The Simpsons has been populated by some of the most talented voice actors for 25 years now, the show wouldn’t be what it is today hadn’t it been for the guest appearances of some of the most talented actors, comedians and musicians in the entertainment landscape. Countless awards and honors line these guest voice actors mantle, but their stint on The Simpsons still reigns as a highpoint on their rise in Hollywood. Without further ado, here are the best Simpsons’ golden era guest voice actors.

15. Elizabeth Taylor as Maggie in “Lisa’s First Word”

She only spoke one word, but it was all that needed to be said. Homer’s angst over Bart and Lisa not calling him by Daddy reached a boiling point in “Lisa’s First Word”. But Homer finally chilled out and realized that he should appreciate Maggie’s silence before she starts talking back. Only until his back was turned did Elizabeth Taylor voice one of The Simpsons’ most heartwarming moments when Maggie uttered her first word “Daddy” before tossing off to sleep. While Ms. Taylor certainly has a plethora of iconic roles to her name, few are as emotionally resonant as when she briefly voiced Springfield’s most iconic baby.

14. Beverly D’Angelo as Lurleen Lumpkin in “Colonel Homer”

Infidelity was a strong theme in early Simpsons’ episodes, but it was only until Lurleen Lumpkin finally wrote down her feelings for Homer in song much to Marge’s teeth-grinding chagrin. Beverly D’Angelo’s performances showcase both her acting and singing chops, able to effectively portray a southern country singer and give the musical touch as well. While her character fell to lesser fates waking up in a ditch, D’Angelo’s early performance in “Colonel Homer” solidified the “Vacation”-ing actress as one of early Simpsons’ best guest voices.

[youtube http://www.youtube.com/watch?v=PCcgPt3VdsM&w=584&h=390%5D

13. Aerosmith as themselves in “Flaming Moe’s”

Many musical acts had passed through the Simpsons recording studio, but the first was Aerosmith great guest act in “Flaming Moe’s”. Watching drummer Joey Krammer being uncomfortably seduced by Mrs. Krabappel was a comedic delight, and Steven Tyler inviting Moe Szylack onstage for “Walk This Way” truly showed that The Simpsons had cemented themselves as a pop culture mainstay.

12. Leonard Nimoy as himself

Nimoy’s first appearance was in “Marge vs. the Monorail” as the celebrity guest rider on the ill-fated monorail’s maiden voyage. While he wasn’t too busy being creeping out his fellow riders with solar eclipse monologues or being confused as a member of the “Little Rascals” by Mayor Quimby, Nimoy’s appearance was wonderful and self-deprecating. Nimoy appeared again as the narrator for “The Springfield Files” before abruptly departing to his car before episodes ends. Without question, Nimoy’s stints on “The Simpsons” were truly out of this world.

11. Patrick Stewart as Number One in “Homer the Great”

In the secret Stonecutters society, Number One’s word remains supreme. He is taut and demanding, and only until Homer proves himself to be too much of a chosen buffoon does Number One make the decision to abandon the Stonecutters in favor of starting the “No Homer’s Society” (No Homers, they can still have one). Stewart’s most famous role is certainly as Captain Jean-Luc Picard in “Star Trek: The Next Generation”. But Stewart achieved comedic icon status when he commandeered the effort to banish Homer’s stupidity forever.

10. Harvey Fierstein as Karl in “Simpson and Delilah”

Just as there are countless Springfieldians who pray for Homer Simpson’s downfall, there are also a select few who strive to make the bald doofus into a better man. The earliest of these was Karl, a suave and utterly confident man who served as Homer’s secretary in “Simpson and Delilah”. While Homer’s new found hair and subsequent success ultimately faded away, Karl yearned to help Homer believe that the fellow behind the follicles had everything he needed to succeed all along. Fierstein’s passionate performance and trademark raspy voice helped give Homer the necessary confidence to succeed in later seasons.

9. John Waters as John in “Homer’s Phobia”

Although Karl was implied to be gay, John Waters’ take as, well, essentially himself in “Homer’s Phobia” was the series’ first full blown exploration into gay commentary. While Homer’s efforts to keep Bart a straight path are undoubtedly hilarious (“Boy, where did you get that shirt?” “It just came out of the closet”), Waters shines throughout the episode as the voice of flamboyant reason, showing Homer that there ain’t nothing wrong with swinging to a different sexual tune.

[youtube http://www.youtube.com/watch?v=T1b6ko1I00A&w=584&h=390%5D

8. Danny DeVito as Herbert Powell in “Oh Brother, Where Art Thou?”

“His life was an unbridled success, until he found out that he was a Simpson.” Homer’s millionaire half-brother Herbert Powell faced an unfortunate demise at the hand of his incompetent brother, and he made it all back with the help of Maggie no less. Herbert Powell is “The Simpsons” touchstone rags to riches back to rags and to riches again story, and DeVito’s angry and fiery performance made Herb a welcome guest addition to the Simpson clan.

7. Ringo Starr, George Harrison and Paul McCartney as themselves

While their performances are part of the Springfield folklore now, it is still absolutely remarkable that “The Simpsons” was able to get all living members of The Beatles at that time to guest star on the show. Ringo Starr’s appearance as the subject of Marge’s portraits was funny and humble. George Harrison’s apathetic take to Homer’s Barbershop Quartet performing on the rooftop of Moe’s Tavern was charming and self-referential. And Paul McCartney’s guidance and encouragement of Lisa’s vegetarian lifestyle was welcoming and heartfelt. The members of the Fab Four definitely gave a fabulous yellow turn when they arrived in Springfield.

6. Jon Lovitz as Various

Lovitz is one of “The Simpsons” most frequent guest stars throughout the years. His earliest appearance was as Marge’s sleazy ex-boyfriend Artie Ziff in “The Way We Was”. Lovitz also appeared Marge’s art teacher Professor Lombardo in “Brush with Greatness” and as Burns’ rival Shelbyville Power Plant owner Aristotle Amadopolis in “Homer Defined”. But Lovitz’ best take was as fierce theatre director Llewlyn Sinclair, who pushed Marge and the rest of the cast of “Oh, Streetcar!” to their absolute limits. Lovitz hilarious larger-than-life characters helped establish the zany and quirky atmosphere that was oh so cherished in “The Simpsons” golden era.

5. Dustin Hoffman as Mr. Bergstrom in “Lisa’s Substitute”

Season 2 of “The Simpsons” was still funny, but not quite on the same quality as subsequent seasons. But the shining beacon of that sophomoric bunch was “Lisa’s Substitute”, where Lisa becomes transfixed by her new charming substitute teacher Mr. Bergstrom. While it was satisfying to see Mrs. Krabappel attempt to seduce Mr. Bergstrom in the vein of Mrs. Robinson in “The Graduate”, the episode’s best moment is when Mr. Bergstrom gives a distraught Lisa a note before departing, saying no more than “You Are Lisa Simpson”. With “Lisa’s Substitute”, “The Simpsons” showed they could still churn our emotional barrel just as well as any live action series. And Hoffman’s take as Mr. Bergstrom was the key to igniting this powerfully heartfelt episode on fire.

4. Michael Jackson as Leon Kompowsky in “Stark Raving Dad”

Michael Jackson was the most popular musician on the face of the earth when he guest starred on “The Simpsons”. So it’s pretty bizarre to see that he isn’t voicing himself, but rather a fat, bald mental patient who believes to be Michael Jackson. Jackson didn’t actually sing the “Happy Birthday Lisa” song (Kipp Lemmon performed it), his trademark quiet speaking voice still worked wonders on the residents of Springfield and the viewers at home alike.

3. Phil Hartman as Troy McClure

Phil Hartman was one of the most talented comedic actors of his generation, and it was only natural that he lend his voice to some of “The Simpson’s” most eclectic personalities. While the disheveled lawyer Lionel Hutz and silver-tongued conman Lyle Lanley were unforgettable roles, his high point was as Springfield’s favorite D celebrity Troy McClure. You might remember him from “Lead Paint: Delicious but Deadly” and “Alice’s Adventures through the Windshield Glass”, but McClure’s best take was when he misguidedly wooed Marge’s sister in “A Fish Called Selma”, giving a top notch satirical take on Hollywood while also belting out one of “The Simpson’s” best musical performances in “Stop the Planet of the Apes, I Want to Get Off!” You’ll never make a monkey out of Mr. Hartman.

[youtube http://www.youtube.com/watch?v=dY8SS_qlchk&w=584&h=390%5D

2. Al Brooks as Hank Scorpio in “You Only Move Twice”

Al Brooks voiced many characters in early episodes of the series’, but only until he voiced good-guy boss/evil villain extraordinaire Hank Scorpio in “You Only Move Twice” were his acting and comedic sensibilities given full spotlight. Scorpio is quick and friendly, ready to give Homer a pair of shoes or throw his own away without hesitation. While we’ll never know if his doomsday device truly succeeded, we’ll always remember Scorpio for his final parting gift to Homer: the ownership rights to the Denver Broncos. D’oh!

1. Kelsey Grammer as Sideshow Bob

From his first maniacal scheme to frame Krusty the Clown in “Krusty Gets Busted” through his attempts to rehabilitate himself while stopping his brother Cecil’s evil plan in “Brother From Another Series”, there is no guest character who has held a stronger grasp on “The Simpsons” that Sideshow Bob. His intelligent, murderous demeanor will flatter and flatten you if he isn’t too busy stepping on garden rakes. Grammer’s distinguished, booming voice brought Bob to life, making him Springfield’s favorite, and most feared, guest resident.