11 Best Simpsons Guest Stars of All-Time (In No Particular Order)

The Simpsons first debuted as a short on The Tracey Ullman Show in April of 1987. Two years later, The Simpsons had its own series on FOX and The Tracey Ullman Show started taping its final episodes. In the years that have followed, children have literally been born, grown up and now have children of their own.

A frightening thought, that.

Yet as old as we get, The Simpsons cast of characters stays the same age. It’s part of what makes the show so timeless – along with its brilliant humor and remarkable ability to predict the future. Now in its 30th season, it seems as though The Simpsons may never die.

Almost anything is possible in the world Matt Groening created, from alien invasions to visits from God and an endless cast of celebrities who’ve found their way to Springfield. Since the show’s early years, stars have jumped on and requested opportunities to perform guest spots on The Simpsons, either portraying themselves in a yellowish Groening makeover or playing a completely fictional character.

There have been way too many guest stars on The Simpsons to remember, but I’ve done my best to put together this list of some of the funniest and most impactful ones. After struggling to keep the list down to just a few top choices, check out some honorable mentions of celebrity Simpsons guest appearances below.

1Jim Varney

The late Jim Varney made his guest spot in season nine, playing Cooder in 1998’s “Bart Carny”. Varney was famous for his popular Ernest character that made numerous appearances in advertising campaigns and films. The Simpsons family visits the carnival where Bart destroys Hitler’s car, which happens to be the main attraction. As payback, Homer and Bart are forced to join as game operators to work off the debt. What a premise.

The two become the nemesis of Cooder and his son – two carny con artists so cunning they end up locking the Simpsons out of their own home. Varney, with his signature southern twang, has some memorable quotes as he goes from rags to falsified riches including his, “Look at me, I’m a millionaire,” which I can still weave into everyday life from time to time.

2Dustin Hoffman

Who could forget one of the most touching scenes in The Simpsons history? It comes at the conclusion of 1991’s “Lisa’s Substitute” in season two, guest-starring Dustin Hoffman as Lisa’s short-lived but impactful substitute teacher Mr. Bergstrom, who leaves abruptly after being transferred to another school.

Part of what makes the guest spot so memorable is what occurs after his departure. This is when viewers really start seeing The Simpsons transition from a crudely-drawn and voiced cartoon in the first season into what it would later become, with great character development, specifically within the family dynamic of The Simpsons household.

Not only do the characters start to become people we can actually identify with, but we also start to realize the show’s ability to not only make us laugh but also tear up just as well. The fact that one of the biggest Hollywood stars lent his voice to the brilliantly written episode helped legitimize The Simpsons as a show that truly connected with audiences.

3MLB All-Stars: Wade Boggs, Jose Canseco, Roger Clemens, Ken Griffey, Jr., Don Mattingly, Steve Sax, Mike Scioscia, Ozzie Smith, and Darryl Strawberry

Season three’s “Homer at the Bat” features a heavy-hitting roster of MLB all-stars in one of the most classic Simpsons episodes ever. When Mr. Burns makes a million-dollar bet that his team will beat the Shelbyville power plant team, he orders Smithers to recruit a lineup of professional Major League Baseball players to work at the plant and thus qualify to sign up to play ball.

Airing in 1992, this is another classic episode from those early years of the series. The episode features some of the most quotable lines in the show’s history.

  • Mr. Burns: “Get rid of those sideburns” directed at Don Mattingly
  • Bart: “Darrrryyyllll” taunt followed by Strawberry’s single tear
  • Ken Griffy, Jr.: “It feels like a party in my mouth, and everyone’s invited.”

4Mark Hamill

1998’s “Mayored to the Mob” in season ten marked the first time Mark Hamill portrayed the iconic Luke Skywalker character since 1983’s Return of the Jedi. First, we see Hamill as Luke when he makes an appearance at Springfield’s Bi-Mon-Sci-Fi-Con. After a nerd riot ensues, Homer saves Mayor Quimby who hires him as his personal bodyguard. Hamill makes an even funnier appearance as himself playing Luke Skywalker later in the episode as part of a live Guys and Dolls stage show singing “Luke, Be a Jedi Tonight.”

5Ramones

The Ramones are hired to perform at Mr. Burns’ birthday party without any explanation, as Burns clearly has no idea who they are when he orders Smithers to, “Have the Rolling Stones killed.” The 1993 season five episode “Rosebud” centers around Burns’ long-lost teddy bear Bobo and is one of the most memorable episodes of The Simpsons ever. While The Ramones cameo is short, it always gets a laugh from me and the clip makes for a great post on a good friend’s birthday timeline.

6Michael Jackson

It was long debated whether Michael Jackson himself or a remarkable sound-alike lent his voice to The Simpsons in 1991 for season three’s “Stark Raving Dad”. Again, this was pre-Internet. Why would the biggest star in the world appear on what was still mostly viewed as a lowbrow cartoon show? There were a lot of reasons to be confused.

First, the voice work was credited to John Jay Smith. That name was completely made up, later revealed to be a pseudonym for Jackson who didn’t want to be credited for the role of Leon Kompowsky – an overweight white man locked in a looney bin for believing he’s M.J. himself. Second, Jackson couldn’t lend his singing voice to the episode due to contractual obligations, so all of the singing including a short sample of “Billie Jean” and “Happy Birthday Lisa” are performed by singer Kipp Lennon. Although Jackson didn’t sing the birthday song in the episode, he did write it.

Thanks to the Internet, all the information is out there. Michael Jackson was a fan of Bart and contacted Matt Groening himself expressing interest to be a part of the show. As a result, Jackson also co-wrote and performed backing vocals on “Do the Bartman” for which he is also uncredited due to contractual obligations.

7Leonard Nimoy

Mr. Spock himself guest stars in more than one episode of The Simpsons including 1997’s “The Springfield Files” in season eight along with Gillian Anderson and David Duchovny from The X-Files. A few years before that, Leonard Nimoy lent his voice to the 1993 episode “Marge vs. the Monorail”. Written by Conan O’Brien, this episode from season four is often considered one of the greatest Simpsons episodes of all-time.

In the episode, Nimoy isn’t afraid to poke fun at himself as the self-obsessed grand marshal of the monorail’s maiden voyage. As he rambles about his vast knowledge of astronomy and his days on Star Trek, it’s clear that none of the townspeople really know or care who he is.

8Rodney Dangerfield

Classic episodes of The Simpsons are loaded with jokes you likely couldn’t get away with today. This is especially true in the episode featuring Rodney Dangerfield. Dangerfield lent his voice to The Simpsons in 1996 on “Burns, Baby Burns” during season eight. Essentially playing himself, Dangerfield’s character is Larry Burns, the long-lost son of Mr. Burns. While he did make some last-minute changes to the script while recording, almost all of his jokes were completely written by the show’s staff attempting to mimic his signature one-liners.

The Simpsons writers found the task more difficult than they thought. As is said in comedy, jokes told with the fewest words are the hardest to write. They did pull out some gems as if written by Rodney himself including “Put her back in, she’s not done yet.” Just one example of something that probably wouldn’t fly today.

9Kelsey Grammer

Kelsey Grammer has been a part of The Simpsons lexicon since its near beginnings. Grammer was already well known to TV audiences as Dr. Frasier Crane from Cheers, so it was hard to mistake his voice when he made his first (and brief) appearance as Sideshow Bob in season one’s “The Telltale Head” in 1991. Since then, he has voiced the character a total of 21 times, so you’d be forgiven for mistaking him as a permanent cast member rather than a Simpsons guest star.

Out of all of Kelsey Grammer’s appearances on The Simpsons, the greatest is arguably the 1993 classic “Cape Feare” from season five. The episode is the first to establish Bob’s elaborate lengths to harm Bart.

10The Beatles (Surviving Members)

Though Paul, George, and Ringo each guested in separate episodes, it was still a dream come true for creator Matt Groening. Since the early days of The Simpsons, one of his goals was to have all three surviving members of The Beatles be Simpsons guest stars. No, they didn’t all happen at the same time. But they happened.

The first was Ringo Starr in 1991’s “Brush With Greatness” from season two when it’s revealed Marge used to paint portraits of Ringo as a young artist and send them to him.

https://www.youtube.com/watch?v=6O68NLaNlXQ

The second was George Harrison‘s appearance in 1993’s “Homer’s Barbershop Quartet” from season five. In the episode, Homer shoves Harrison aside to make way for the brownie spread.

The trifecta was completed in 1995 with Paul McCartney and then-wife Linda in “Lisa the Vegetarian” from season seven. There’s also a crazy Easter egg found in the ending credits of this episode, which is now easily accessible thanks to the Internet (check it out at the end of the clip below).

11Stephen Hawking

Physicist Stephen Hawking has lent his “voice” to a few episodes of The Simpsons, but the first and probably best known is from 1999’s “They Saved Lisa’s Brain” from season ten. Lisa is accepted into the Springfield Mensa chapter. She’s joined by Comic Book Guy, Professor Frink, Dr. Hibbert, and others. But after the group gains control of Springfield, someone smarter than the Mensa members needs to expose their wrongdoings. Writers immediately thought of Hawking to portray himself in the episode. Being a fan of the show, he was on board from the beginning. But Hawking almost didn’t make it to the recording session. Hawking’s wheelchair broke down two days before his trip to Los Angeles. Luckily, his technicians pulled a 36-hour shift to repair his chair just in time. He ended up making the session, though he was 40 minutes late.

In the episode, Hawking shows his ability to poke fun at himself on numerous occasions. According to writer Matt Selman, Hawking only had one stipulation with the original script. He did not want to appear to be intoxicated in his final scene with Homer in Moe’s Tavern.

The Simpson Guest Star Honorable Mentions

Dave Thomas as Rex Banner in “Homer vs. the Eighteenth Amendment” (Season 8, 1997)

https://www.youtube.com/watch?v=M0UdBNzibns

David Hyde Pierce as Cecil Terwilliger in “Brother from Another Series” (Season 8, 1997)

Phil Harman as Troy McClure/Lionel Hutz (Various Episodes)

https://www.youtube.com/watch?v=q99ZluaCL_c

More Simpsons Guest Stars?

Do you have any favorite Simpsons guest stars that you think should be on this list? Please let us know in the comments.