Over the course of two and a half decades and more than 500 episodes, The Simpsons has seen its fair share of celebrity appearances and then some, rivaled only by Saturday Night Live as America’s premier destination for stars looking to poke fun at themselves. And while there have certainly been a few duds over the years, among the rest are some of the funniest guest spots in the history on television.
This list could easily be twice as long, but after going through the show’s 25 seasons, we’ve narrowed The Simpsons’ gargantuan guest star roster down to its 100 best. You won’t see psuedo-cast members like the late Phil Hartman or Marcia Wallace on here, but otherwise your favorite will probably be making an appearance.
100. Albert Brooks as Jacques
Episode: “Life on the Fast Lane”
Part of a select circle of Simpsons guest stars that have appeared on the show more than a half-dozen times, Brooks is a series staple. One of his early roles is one of his best: The slimy Frenchman Jacques, who tries in vain to woo a weary Marge away from her dopey husband.
Marge: “What’s brunch?”
Jacques: “You’d love it, it’s not quite breakfast, it’s not quite lunch, but it comes with a slice of cantaloupe at the end.”
99. Charlie Rose
Episode: “Kill the Alligator and Run”
In an episode that also stars Kid Rock and rapper Joe C., the restrained Rose easily comes out as the bright spot. You expect rock stars to do wild and crazy things, but there’s something about a PBS mainstay threatening murder that makes this cameo great.
“I’m gonna kill you, Homer. You are so dead.”
98 – 96. Alec Baldwin, Kim Basinger and Ron Howard
Episode: “When You Dish Upon a Star”
Back when they were still together, Baldwin and Basinger proved solid comic foils for Homer’s starstruck antics. Though at the time Howard had the most experience in comedy, Baldwin showed a pre-30 Rock knack for timing that definitely carried over to his misadventures with Liz Lemon.
Baldwin: “We’d want another chance if one of us made a bad film, right?”
95. Martin Sheen as Sgt. Seymour Skinner
Episode: “The Principal and the Pauper”
Though Sheen’s stunt-casting of a long-lost Vietnam vet was meant to recall his roles in movies like Apocalypse Now, his turn as the “real” Seymour Skinner came to represent what many fans considered to be the series shark-jumping moment. That doesn’t mean that Sheen doesn’t deserve respect for doing an admirable job on a thankless task, but let’s follow Mayor Quimby’s advice and never mention this episode again.
Sgt. Seymour Skinner: “No, just captured. It’s kind of a funny story, really. After five years in a secret P.O.W. camp, I was sold to China for slave labor. And since ‘77 I’ve been making sneakers at gunpoint in a sweatshop in Boo-Haun.”
Marge Simpson: “That’s not a funny story.”
Sgt. Seymour Skinner: “Well, I guess you had to be there.”
94. Danny DeVito as Herb Powell
Episode: “Oh Brother, Where Art Thou?”
Years before Frank Grimes showed what the real world would think of the Simpson family, Homer was brought down to Earth by his own newfound brother, Herb. DeVito played it mostly straight as his company was brought down by Homer’s terrible design decisions. Though Herb and Homer would later reconcile in another episode, DeVito’s incredulity helped give “Oh Brother” one of the few truly down-note endings in the series history.
“People don’t want cars named after hungry old Greek broads.”
93. Lucy Lawless
Episode: “Treehouse of Horror X”
Halloween episodes are ideal for bringing in guest stars that would otherwise have no place in Springfield, and Lawless made the most of it as a not-so-helpless captive of Comic Book Guy. It’s not the best Treehouse skit in the world, but Lawless deserves credit for being so game to make fun of her Xena persona.
Lisa: “Hey, Xena can’t fly.”
Lawless: “I told you, I’m not Xena. I’m Lucy Lawless.”
92. Kirk Douglas as Chester J. Lampwick
Episode: “The Day the Violence Died”
This old episode is perhaps even more relevant today considering the legal scrapes that creators of Superman and The Avengers are enduring. Douglas is perfect as that the crotchety old Lampwick, fighting for the rights to Itchy and Scratchy—you expect your hobos to have some crunch, but this was like a bowl of cockroach cereal.
“Before I came along, all cartoon animals did was play the ukulele. I changed all that.”
91. Willem Dafoe as The Commandant
Episode: “The Secret War of Lisa Simpson”
Dafoe’s range seems to be somewhere between “creepy psychotic supervillain” and “creepy psychotic serial killer,” so it was a nice change of pace to see him in a typical drill sergeant role. We’re still waiting for him to show up in a Treehouse of Horror episode as himself.
The Commandant: “Lights out!”
[The lights go out and a thump is heard.]
The Commandant: “Ow! Damn it! Lights on! Lights on!”
90. Joe Namath
Episode: “Bart Star”
Years after inspiring Homer’s mother with his luscious locks, Namath stopped by the Simpson home after his car broke down. The sage advice that he gave a struggling Bart will stay in all of our hearts forever.
Bart: “I cannot believe you are here! Do you think maybe you could give me some pointers?”
Namath: “Sure! There’s only one thing you need to know to be a great quarterback.”
Mrs. Namath: “Joe, honey, I fixed it! It was just vapor lock!”
Namath: “OK, look, I’ve gotta run. Remember what I told you.”
89. Jim Varney as Cooder
Episode: “Bart Carney”
Most well-known for his starring role in the Ernest franchise, Varney fit surprisingly well into the stolen shoes of carny grifter Cooder. Some criticized the episode’s dim view of carnival workers, but it’s nothing compared to the giant troll stereotypes perpetuated by Ernest Scared Stupid.
“Son, if you don’t finish your cotton candy, you won’t get your snow cone.”
88. Linda Ronstadt
Episode: “Mr. Plow”
Sometimes famous people are brought on The Simpsons for no other reason than to laugh at a straightforward celebrity in a wacky situation. And you know what? Sometimes that’s alright, especially if you can sing the Mr. Plow song in Spanish as well as Ronstadt.
“Señor Plow no es macho / Es solamente un borracho.”
87. John Goodman as Meathook
Episode: “Take My Wife, Sleaze”
It’s odd that Goodman hasn’t been on The Simpsons more often—his comic timing and sometimes volatile demeanor make him a perfect fit for the series. If appearing on the show means he has to play the Marge-stealing leader of a biker gang, well, we’ll take it.
“Homer… Homer… stop. We’ve given up our violent ways. We just wanna live peacefully… with your wife.”
86. Mel Brooks
Episode: “Homer vs Patty and Selma”
Contrary to Linda Ronstadt, Mel Brooks is a legend in comedy, and yet here he’s still the one acting as the straight man. To be fair, he’s probably tired of everyone telling him to be funny, as evidenced by Homer and Chief Wiggum’s fanboyish demands to recreate a skit.
“Listen, why don’t you play Carl Reiner, and let me play police chief Wiggum? I hate Carl Reiner!”
85. Stephen Colbert as Colby
Episode: “He Loves to Fly and He D’ohs”
With Colbert’s extensive voice acting experience on everything from The Venture Bros. to Harvey Birdman: Attorney at Law, it’s surprising that Colbert wasn’t on The Simpsons sooner. Though he’s obviously got a decent range, at some point the showrunners decided they basically wanted Colbert’s character to be more or less the same one he plays on his parody pundit show.
“Okay Homer, I don’t know anything about planes, but I know about you. You have what made America great: no understanding of the limits of your power and a complete lack of concern for what anyone thinks of you. So you’ll land that plane. And do you know why? Because I heard some guy say you couldn’t.”
84. Dennis Franz as “Homer”
Episode: “Homer Badman”
Sometimes the quickest guest starring roles are the best. Playing on the fact that he’d probably be perfect as a live-action Homer Simpson, Franz plays himself playing an “evil” Homer in a Lifetime-style TV movie. It’s a throwaway joke, but one we’d be willing to watch for two hours.
‘Ashley’: “No, Mr. Simpson, that’s sexual harassment. If you keep it up, I’ll yell so loud the whole country will hear!”
‘Homer’: [laughs] “With a man in the White House? [laughs] Not likely!”
83. Eric Idle as Declan Desmond
Episode: “‘Scuse Me While I Miss the Sky”
Even if you don’t recognize his name, you’ve probably seen Eric Idle in A Fish Called Wanda or one of the Monty Python flicks. Barring that, you at least have to remember his voice. Even in documentary-filmmaker mode, it’s unmistakably the same guy who lead the singalong while crucified in The Life of Brian.
“America is supposed to be democracy. But in the school yard, cool rules. And Springfield’s Machiavelli of the monkey bars is one Bartholomew Simpson. On today’s royal agenda; digging up dirt clods to throw at his school chums.”
82. John Waters as John
Episode: “Homer’s Phobia”
Though The Simpsons tends to magnify personalities, Waters was actually toned down in comparison to his usual zaniness. It helps make his character more relatable to the audience and more importantly to Homer, who like a sad amount of people in the ‘90s, still had some issues with homosexuality.
“Homer, I won your respect, and all I had to do was save your life. Now, if every gay man could just do the same, you’d be set.”
81. Penny Marshall as Ms. Botz
Episode: “Some Enchanted Evening”
The grotesque Ms. Botz is terrifying in part because of the odd techniques of early Simpsons animation, but Marshall helped a lot with her grizzled, unsettling voice. It’s a wonder the character has never showed up again in any major way. Maybe Marshall figured she’d go out on top.
“You’re going to watch this tape, and you’re going to do what I say or I’m going to do something to you. And I don’t know what that is because everyone has always done what I say!”
80. Cloris Leachman as Mrs. Glick
Episode: “Three Men and a Comic Book”
Leachman only played the elderly Mrs. Glick for the one episode, but her performance informed the definition of the character for years afterwards. If only her grisly war flashbacks came with her.
“Filthy! But genuinely arousing.”