The 15 Most Memorable Guest Stars on The Simpsons, Ranked
The world of The Simpsons is filled with unforgettable personalities, but many of these beloved characters are voiced by the same talented actors who cover the main cast. Voice acting legends like Harry Shearer, Hank Azaria, and Dan Castellaneta have worked their magic over the years, but there are occasions when a certain role requires a fresh face and a unique voice.
Celebrities often have varied motivations for lending their voices to this iconic show. Even if they are simply keeping their kids happy by appearing, their performances can leave a lasting impact, transcending the typical one-off guest spot. Some have added to the humor, while others have deeply influenced the show’s primary characters, ultimately reshaping the series’ tone.
While we’ve seen the occasional lackluster celebrity cameo in Springfield, there are a plethora of standout moments. Here’s a countdown of the top fifteen guest stars who have made a significant mark on The Simpsons.
15. Barry White
Barry White’s rich, smooth voice is legendary in music, and his guest appearance in Season 4’s “Whacking Day” brings pure hilarity. In a scene where he learns about the bizarre Springfield tradition of beating snakes, his shocked reaction, “Oh God, no. You people make me sick!” perfectly flips the expectation. Later on, he humorously sings to lure the snakes away. His presence doesn’t overshadow the plot; instead, it contributes humor and surprise.
14. George Harrison
Among the Fab Four, The Simpsons managed to feature three Beatles. George Harrison’s cameo in Season 5’s “Homer’s Barbershop Quartet” stands out, not for his dialogue, but for how Homer reacts to him. When Homer meets Harrison, he’s more interested in where to find a brownie than the fact he’s talking to a Beatle. This absurdity, coupled with Harrison’s deadpan delivery, highlights how best to incorporate celebrity cameos without drowning the plot in reverence.
13. Johnny Cash
Johnny Cash takes on the role of Homer’s spiritual guide in the Season 8 episode “El Viaje Misterioso de Nuestro Jomer,” providing a depth that enhances the surreal experience Homer undergoes after consuming some particularly spicy chili. Cash’s soothing voice lends gravity to this bizarre episode, and his character’s wisdom and humor resonate well with viewers.
12. Donald Sutherland
In “Lisa the Iconoclast,” Donald Sutherland plays Hollis Hurlbut, a museum curator who embodies the straight-man role. His serious tone adds a comedic layer to the absurdity of Lisa’s antics. Sutherland’s humorous ad-lib about getting over Chester A. Arthritis is a standout line, showcasing his ability to blend realism with whimsy.
11. Michelle Pfeiffer
Michelle Pfeiffer voices Mindy Simmons in “The Last Temptation of Homer,” presenting Homer with a tempting alternative to Marge. Mindy’s charm and love for life resonate with Homer, and Pfeiffer’s sultry performance captures the intrigue and vulnerability in the character, making her an unforgettable part of Homer’s romantic misadventures.
10. Danny DeVito
Danny DeVito portrays Herb Powell, Homer’s half-brother, in several episodes. His character represents the duality of Homer’s potential, showing what he could have been under different circumstances. DeVito’s performances bring credibility and warmth that make Herb a memorable character in the series.
9. Patrick Stewart
Patrick Stewart lends his voice to Number One in “Homer the Great,” delivering a remarkably humorous portrayal of a secret organization leader. His grandiose line delivery adds to the absurdity of the situation, showcasing how Stewart’s talent enhances the comedic elements of the series.
8. John Waters
John Waters’ appearance as John in “Homer’s Phobia” is not only memorable, but crucial in addressing stereotypes about the LGBTQ+ community. Waters gives the character depth and humor while illuminating societal issues that remain relevant, making it a standout cameo that provoked thought in the midst of comedy.
7. Glenn Close
Glenn Close voices Mona Simpson, Homer’s long-lost mother, in “Mother Simpson.” Her character enriches Homer’s backstory and emotional depth, compelling fans to consider how he may have turned out had he been raised differently. The warmth and connection between Mona and Homer illuminate some of the show’s most heartfelt moments.
6. Dustin Hoffman
Dustin Hoffman embodies Mr. Bergstrom in “Lisa’s Substitute,” bringing emotional resonance to Lisa’s journey of self-discovery. Hoffman’s performance showcases the depth of voice acting, successfully transitioning from comedic moments to poignant themes that strike a chord with viewers.
5. Meryl Streep
In “Bart’s Girlfriend,” Meryl Streep voices Jessica Lovejoy, whose character is both alluring and mischievous. Streep’s ability to make Jessica distinct allows for a different dynamic in Bart’s character development, emphasizing her impact on the show.
4. Albert Brooks
Albert Brooks has voiced numerous characters over the years, but his portrayal of Hank Scorpio in “You Only Move Twice” is a fan favorite. The blend of humor and villainy Brooks brings to Scorpio makes the character unforgettable, with memorable lines that capture the essence of the show’s comedic brilliance.
3. Joe Mantegna
Joe Mantegna’s Fat Tony first appeared in “Bart the Murderer,” but his character quickly became a staple in Springfield. His distinct voice adds authenticity to the mobster persona while allowing for comically absurd situations to unfold, elevating the series’ humorous undertones.
2. Kelsey Grammer
Kelsey Grammer’s Sideshow Bob has become a central figure in The Simpsons. With his sophisticated sense of villainy and a flair for the dramatic, Grammer nails every performance, making Bob one of the show’s most iconic characters with episodes revolving around his elaborate schemes.
- Phil Hartman
- Phil Hartman was a cornerstone of The Simpsons, contributing his voice to a range of beloved characters, including Troy McClure and Lionel Hutz. His performances combined charm and wit, leaving a lasting impact on the series. Hartman’s departure marked a significant shift in the show’s energy, but his legacy endures through the classic moments he enriched.
