Cartoons | Pop Culture | TV | 90s

20 Of The Best Guest Stars From The Simpsons

The Simpsons will be continuing at least until Season 30! Fox has confirmed that their show will surpass the record of longest running scripted series with a record 669 episodes. The Simpsons is currently in season 28 and continues to be a staple in television viewing.

It would be hard to find a person who hasn't seen at least ONE episode of the Simpsons. One of the best parts of The Simpsons has always been the guest stars. Each season is filled to the brim with guest voices of celebrities, some playing themselves while others get a new character. Lets take a look at some of the best guest stars in the series history.

       Giphy    

20. Herb Powell

       Giphy    

Danny DeVito provided the voice for Homer's brother, and helped him design a car. He then went bankrupt (obviously because of Homer) and then came back later trying to make more money.

19. Mark Hamill

       Giphy    

It's always nice when a celebrity can make fun of themselves. Mark Hamill is no stranger to voice over work, and totally nailed his episode on the Simpsons.

18. Alex Trebek

When Marge goes on Jeopardy, she wasn't expecting to have to pay back the money she wagered. Luckily she could outrun the host of the show.

17. Artie Ziff

       Giphy    

Artie Ziff is the worst. He is a vial awful man that makes Marge feel like garbage. At least his terrible behavior leads her to Homer, but Jon Lovitz does a great job at creating a truly terrible character.

16. Mickey Roone

       Giphy    

Mickey Rooney tries to give Milhouse a pep talk, but instead steals his role as Fallout Boy. So ridiculous.

15. Cecil Terwilliger

       Giphy    

I think one of may favorite moments was when Cecil, voiced by David Hyde Pierce (aka the actor who plays Frasier's brother) had to "guess who" when Bart covered his eyes and his answer was "Maris". A moment that a lot of kids probably didn't understand, but as a fan of both The Simpsons and Frasier still makes me laugh so much.

14. The cast of Cheers

       Giphy    

Ted Danson, Rhea Perlman, Woody Harrelson, John Ratzenberger and George Wendt all make an appearance when Homer is trying to find a new bar and stumbles upon Cheers. Homer quickly leaves when Norm gets a little bit upset because Woody won't give him another beer, but it gives a hilarious look at what the usually fairly clean cut show could have been.

13. Buzz Aldrin

       Giphy    

Someone who has literally been in outer space got to have a little bit of fun voicing himself on the Simpsons. Really shows that just about everyone wants to be on The Simpsons.

12. Conan O'Brien

       Giphy    

Conan used to write for the Simpsons, so it was only a matter of time before he returned to voice his new talk show persona on the show. "Only I may dance" is just one of the greatest moments.

11. Bleeding Gums Murphy

       Giphy    

Bleeding Gums Murphy's death is quite sad. Poor Lisa, she had such love for him but at least she got his saxaphone. I hope she cleaned it before using it, he apparently never went to the dentist and if his name is any indication you should definitely sanitize it before playing it.

10. Stephen Hawking

       Giphy    

I didn't know this, but apparently they actually got Stephen Hawking! I had thought they just used a computerize voice, but they actually had Hawking come into the recording studio.

9. Adam West

       Giphy    

Adam West will always be Batman to me. His ability to make fun of himself and acknowledge the goofy Batman series he was on makes him all the better. It's nice that he got to continue being the goof that he is over on Family Guy!

8. Johnny Cash

Can you imagine having to be the one to call Johnny Cash's representatives and say "yes we would like Mr. Cash on our show; however we would like him to play a mystical coyote and try to attack Homer, so we will need him to growl". Or better yet, being the agent who pitched this to Johnny Cash? Oh, to be a fly on that wall!

7. Larry Burns

       Giphy    

Another long lost brother scenario, except this time it's Mr. Burns. His brother is voiced by Rodney Dangerfield who is essentially playing himself.

6. Hugh - Lisa's future husband

       Giphy    

Another voice shocker - Mandy Patinkin a.k.a. Ingio Montoya voiced Lisa's fiancé in the episode where she saw her future!

5. Leon Kompowski

       Giphy    

He claims to be a bricklayer from New Jersey, but we all know he is Michael Jackson. They think he is crazy, but who knows. He sings a great song to Lisa for her birthday and dances like the real thing.

4. Jessica Lovejoy

       Giphy    

Do you know who voices Jessica? I sure didn't. The one, the only Meryl Streep! I mean, that woman can do everything!

3. Mona Simpson

       Giphy    

She may not be the best mother out there, but she is voiced by Glen Close! That is pretty impressive if you ask me.

2. Hank Scorpio

       Giphy    

One of the greatest episodes of the entire series, Hank Scorpio gives Homer a new job and is pretty much one of the craziest bosses anyone could have. Albert Brooks voices him to perfection, playing the villain-style guy that you can't help but love.

1. Sideshow Bob

       Giphy    

Sideshow Bob is just about the greatest guest star ever. He is a ridiculous character made 100% by the fact that he is voiced by Kelsey Grammar -aka Frasier. Could you imagine how he must have felt back in the 90's when he would go from a Frasier taping to voicing a felon/clown?Who was your favorite guest star on The Simpsons? Share yours in the comments!

More Throwbacks

TV

'Beverly Hills: 90210' Revival Looks Like It Will Feature A Lot Of Familiar Faces

Who else remembers planning their entire week based on when Beverly Hills: 90210 was going to be on TV? It wasn't like we could record it easily, blank VHS tapes were pricey, so we had to watch it when it was on or miss out. Watching Brenda, Kelly, Dylan, Brandon, Donna, and everyone else hand out and get into all kinds of mayhem was the highlight of our weeks. When it ended, we were all a bit sad, but then they brought it back with a new spin-off.  The new show tried to catch that same teen spirit, but

TV

'SpongeBob SquarePants' Creator Stephen Hillenburg Dies At 57

It's a sad day in the world of cartoons, as Nickelodeon has confirmed the passing of SpongeBob SquarePants creator Steven Hillenburg. The iconic TV show writer and producer with a long career and a hand in creating a lot of our favorite moments in animation. Hillenburg actually didn't go to school for television writing, instead studying "Natural Resource Planning and Interpretation with an emphasis on marine resources" according to Variety. Obviously, this would come into play later in his career. He started working in television after going back to school to study Experimental Animation, and eventually became a writer and

TV

Netflix Is Bringing All Of Your Favorite Roald Dahl Stories Back In A New Animated Series

There are a few iconic storytellers we can all agree influenced our childhoods, and Roald Dahl is basically guaranteed to make everyone's list. His classic stories like Charlie and the Chocolate Factory, Matilda, and James and the Giant Peach have been loved by children for decades. It doesn't matter if you're reading the book or watching one of the many movies based on one of his novels, because Dahl's ability to create these magical little worlds manages to transcend format and remain enjoyable no matter what.Dahl's characters are nothing short of iconic. Whether it's the six-year-old Matilda who has

80s

Die Hard's Reginald VelJohnson Reveals How Al Powell Got Him Cast On Family Matters

Watching Die Hard is like watching a little piece of history. It truly has remained one of the greatest movies of all time no matter how much time passes. Maybe we didn't know how special it was when we first saw it, but as the decades go on, it has become clear that it's a true classic that is basically required viewing for every single person. Everyone obviously thinks of Bruce Willis when they think about Die Hard, which makes sense because he embodies John McClane in a way that makes him feel real, but he's not the only iconic

90s

Trailer For New Nickelodeon Documentary Has Your 90s Favorites Spilling All The Secrets

Nickelodeon wasn't just a television network, it was basically a generation. Kids all over the country were bonded in this weird little family, obsessing over shows that our parents just couldn't possibly understand. They were for us. They weren't made to appeal to our parents, they were made for our enjoyment and so we felt a special connection to them unlike any other shows. Nickelodeon is still going strong today, but it's hard to remember that there was a time before the iconic kids network came around. The company may be a juggernaut now, but how did it get started?

TV

Woman Surprised Her Mom With A Trip To 'Sesame Street' And It's The Cutest Thing You'll See All Day

"Sunny day! Sweepin' the clouds away! On my way to where the air is sweet! Can you tell me how to get, how to get to Sesame Street?" It's a song we all know off by heart no matter how old we are now because it was literally one of the most important parts of our days. Sesame Street was a staple in almost every household. Those Muppets were our teachers and our friends before we made our way into elementary school or daycare, and they gave us a lot of life lessons that taught us how to be a