8 Best Guest Stars on The Simpsons

James Woods took guest starring to the next level on The Simpsons, working behind a Kwik-E-Mart counter for research before heading off to battle aliens on a distant planet.

James Woods

Buzz Aldrin, a moonwalker, on The Simpsons? Yes! Only this show could get him to say, "Careful! They re ruffled!" He's truly lived out every American's dream.

Buzz Aldrin

Skateboarding legend Tony Hawk helped celebrate The Simpsons' 300th episode with an epic, superpowered skateboarding duel against Homer in "Barting Over."

Tony Hawk

Jon Lovitz has played multiple memorable characters, including Marge s prom date Artie Ziff, her theater director Llewellyn Sinclair, and her art teacher Professor Lombardo.

Jon Lovitz (Various)

The late Phil Hartman was irreplaceable on The Simpsons, bringing to life iconic characters like Lionel Hutz, Troy McClure, and the villainous Lyle Lanley, enriching every episode he was in.

Phil Hartman (Various)

Kelsey Grammer s portrayal of Sideshow Bob is legendary, making him a recurring character since season one. David Hyde Pierce, his Frasier co-star, played Bob s brother Cecil.

Kelsey Grammer (Sideshow Bob)

Sting showed his heroic side on The Simpsons, leading a parody of "We Are the World" and tirelessly digging to save Bart from a well, proving his dedication to fans.


Leonard Nimoy s role in Marge vs. the Monorail cemented the episode s status as a fan favorite. He saved Krusty and then teleported away, adding a touch of magic.

Leonard Nimoy