The 100 Greatest Simpsons Guest Stars

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The 100 Greatest <i>Simpsons</i> Guest Stars

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”
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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.

Memorable Quote:
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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
Baldwin: “We’d want another chance if one of us made a bad film, right?”
[Awkward silence]

95. Martin Sheen as Sgt. Seymour Skinner
Episode: “The Principal and the Pauper”
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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.

Memorable Quote:
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?”
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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.

Memorable Quote:
“People don’t want cars named after hungry old Greek broads.”

93. Lucy Lawless
Episode: “Treehouse of Horror X”
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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.

Memorable Quote:
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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
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”
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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.

Memorable Quote:
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”
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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.

Memorable Quote:
“Son, if you don’t finish your cotton candy, you won’t get your snow cone.”

88. Linda Ronstadt
Episode: “Mr. Plow”
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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.

Memorable Quote:
“Señor Plow no es macho / Es solamente un borracho.”

87. John Goodman as Meathook
Episode: “Take My Wife, Sleaze”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
‘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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
“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”
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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.

Memorable Quote:
“Filthy! But genuinely arousing.”

79. Sab Shimono as Mr. Sparkle
Episode: “In Marge We Trust”
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The main plot of this episode is an entertaining and heartfelt exploration of faith featuring Marge and Reverend Lovejoy, but everyone just remembers it as the Mr. Sparkle episode. Likewise, Shimono is an accomplished film voice actor, but his turn as the coincidentally Homer-shaped Japanese fishbulb mascot outshines everything else on his IMDb page.

Memorable Quote:
[Translated from Japanese] “I’m disrespectful to dirt. Can you see that I am serious?”

78. Donald Sutherland as Hollis Hurlbut
Episode: “Lisa the Iconoclast”
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Kiefer has been on the show a few times, but his dad’s even-tempered performance as a hardcore historian has stood the test of time. Very few can pull off gravitas and steal a silver tongue from a corpse in the same episode.

Memorable Quote:
“That’s preposterous. Now get out! You’re banned from this Historical Society. You, and your children, and your children’s children! ...for 3 months.”

77 – 76. Paul and Linda McCartney
Episode: “Lisa the Vegetarian”
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Though not particularly funny, the sheer star power of the McCartneys in cartoon form is a little staggering. Paul in particular added a lot to The Simpsons mythos when he stipulated that his appearance hinged on Lisa’s vegetarian transformation remain for the rest of the series.

Memorable Quote:
“Linda and I both feel strongly about animal rights. In fact, if you play ‘Maybe I’m Amazed’ backwards, you’ll hear a recipe for a really ripping lentil soup.”

75. R. Lee Ermey as Col. Hapablap
Episode: “Sideshow Bob’s Last Gleaming”
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Ermey has played the same hard-nosed drill sergeant since Full Metal Jacket, but that’s what works so well here. Taking that no-nonsense attitude and applying it to goofy phrasing is comedy gold, and Ermey pulls it off without a hitch.

Memorable Quote:
“Sweet Enola Gay, Son! I’m going to come in there and corpse you up—corpse you up and mail you to mama!”

74. Mark Hamill
Episode: “Mayored to the Mob”
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Though he’ll forever be known as Luke Skywalker, Hamill has done some impressive voice work since the original Star Wars movies. Besides playing himself in the episode, he also has a turn at a couple other side characters in the episode.

Memorable Quote:
“You know, I’m here today as Luke Skywalker, but I’m also here to talk about Sprint. As you can see here, you stand up to save up to seventeen cents a month over the more dependable providers.”

73. Lisa Kudrow as Alex
Episode: “Lard of the Dance”
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As the cool new preppy kid in school, Kudrow pulls less from Phoebe on Friends and more from her turn as half of Romy and Michelle’s High School Reunion. It was a perfectly cromulent creative choice.

Memorable Quote:
Alex: “Calm down, Lisa. DMY.“
Lisa: “What’s DMY?“
Alex: “Don’t mess yourself.“
Lisa: “Eww.“
Alex: “Yeah, that’s why we changed it to DMY.“

72. Bob Hope
Episode: “Lisa the Beauty Queen”
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This is one of those times in The Simpsons’ early years when you could tell the show really made it. Though he’s been all over the world doing hundreds, probably thousands of shows in his life, getting Bob Hope is still a coup; one of his few lines reflected the fact.

Memorable Quote:
“Hello, this is Bob ‘What the hell am I doing in Springfield?’ Hope.”

71. Steve Allen
Episode: “‘Round Springfield”
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Another comedy juggernaut, Steve Allen’s stint is also short in what’s otherwise a Bleeding Gums Murphy-centric episode. Decades later, he was still at the top of his game, elevating even the few lines he had.

Memorable Quote:
How to Make Love to Steve Allen, from the author of Happiness Is a Naked Steve Allen, Journey to the Center of Steve Allen, and The Joy of Cooking Steve Allen.”

70. Betty White
Episode: “Missionary Impossible”
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On the list of things that make national treasure Betty White great, her one-off Simpsons bit is probably pretty far from the top. On the other hand, just saying Betty White out loud increases the chances of a Golden Girls episode appearing on TV, so we’ll go ahead and give her the spot.

Memorable Quote:
[during the PBS pledge drive] “And if you watch one minute without contributing, you’re a thief! A common thief!”

69 – 67. Daniel Clowes, Art Spiegelman and Alan Moore
Episode: “Husbands and Knives”
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These musclebound terrors are actually just Hulked-out versions of the most respected comic book writers and artists in the entire medium. Moore, the staunch anti-Hollywood creator of “Watchmen” and “V for Vendetta” was a particularly good get; of course it was Milhouse who begged him to sign “Watchmen Babies: V for Vacation.”

Memorable Quote:
Bart: “Alan Moore, you wrote my favorite issues of ‘Radioactive Man.’”
Alan Moore: “Oh really, so you liked that I made your favorite superhero a heroin-addicted jazz critic who’s not radioactive?”

66. Lawrence Tierney as Don Brodka
Episode: “Marge Be Not Proud”
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As fun as Tierney’s mall cop was the in the episode, the stories behind the scenes are even better. Apparently he outright refused to say lines that he didn’t like and added a weird Southern accent to everything else. If only Betty White was so crazy.

Memorable Quote:
“If I wanted smoke blown up my ass, I’d be at home with a pack of cigarettes and a short length of hose.”

65. Sam Neill as Molloy
Episode: “Homer the Vigilante”
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Most voice actors play younger, but few skew older like Neill did with elderly cat burglar Molloy. He’s almost unrecognizable—his silky, wizened accent sounds more like Pierce Brosnan’s dad than the guy from Jurassic Park.

Memorable Quote:
“I sincerely regret any inconvenience that I may have caused. And although I have stolen your material goods, let me assure you that your dear town has stolen my heart.”

64. Willie Nelson
Episode: “Behind the Laughter”
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Though he’d been on episodes previous, the making-of episode “Behind the Laughter” revealed that Nelson had strong ties to Springfield. Namely, he’d been bros with Dr. Julius Hibbert. Rumor has it that “Always on My Mind” is really about his Kegmeister.

Memorable Quote:
“I would do anything for Kegmeister Julius.”

63 – 62. David Duchovny and Gillian Anderson as Mulder and Scully
Episode: “The Springfield Files”
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Interviewed at Comic-Con, both actors admitted that they barely remember taping their sizable Simpsons roles at the height of The X-Files’ popularity. It shows in their nonplussed performances, but in a way it works; to paranormal investigators, even a case in a place as insane as Springfield is just another job.

Memorable Quote:
Mulder: “Are we alone in the universe? Impossible. When you consider the wonders that exist all around us… voodoo priests of Haiti, the Tibetan numerologists of Appalachia, the unsolved mysteries of Unsolved Mysteries… The truth is out there.”

61. Jeff Goldblum as MacArthur Parker
Episode: “A Fish Called Selma”
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Unlike fellow Jurassic Park star Sam Neill, Goldblum’s plays more of a side character as Troy McClure’s Hollywood agent. Still, Parker gets McClure to star in the Planet of the Apes musical, and no one can deny that the world is a better place for that.

Memorable Quote:
“Listen, you can’t buy that kind of P.R., but you can get it for nothing by having a baby, which, by the way, your insurance will cover, except for the deductible which I’ll reimburse you for if you get the part which you will if you have a baby.”

60 – 59. John Madden and Pat Summerall
Episode: “Sunday Cruddy Sunday”
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This is another instance where celebrities playing it perfectly straight with silly dialogue works perfectly. In an episode with tons going on, an ESPN-style recap of the proceeding just fits.

Memorable Quote:
Summerall: “Well John, what did you think of tonight’s episode?”
Madden: “I loved it! The last-minute addition of Wally Kogen to the line-up was a bit of a gamble, but it really paid off.”
Summerall: “Marge and Lisa painting eggs? Did that work for you?”
Madden: “Ho, ho, big time! They came off the bench with a huge effort that allowed Homer and Bart to make some significant gains.”

58 – 57. George Carlin and Martin Mull as Seth and Munchie
Episode: “D’ohin in the Wind”
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Most guest stars exist to move along the plot or to deliver a quick joke, but it’s rare to see them facilitate any kind of character development. Seth and Munchie offer a window into the groovy world Homer missed while his mother was off being an environmental radical. It helps that Carlin and Mull are totally believable as stoner uncles.

Memorable Quote:
Seth: “We used to have a bus.”
Munchie: “In a way, the ‘60s ended the day we sold it. December 31st, 1969.”

56. Ringo Starr
Episode: “Brush with Greatness”
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It’s funny to think that the least-popular Beatle is featured the most prominently in a Simpsons episode (though it does make a sad amount of sense). There’s something sweet in the sincerity of the joke about a man in the biggest band in the world still going through his back catalog of fan mail. You really believe that if any of them would actually do that, it’s Ringo.

Memorable Quote:
“Dear Sally. In response to your letter of December the 12th 1966, me favourite colour is blue, and me real first name is Richard. Thanks for the snapshot. You’re a real cute bird. Love, Ringo. PS: Forgive the lateness of my reply.”

55 – 53. Spinal Tap
Episode: “The Otto Show”
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It was only a matter of time before series regular Harry Shearer pulled in Christopher Guest and Michael McKean to reunite Spinal Tap, the best bad band that ever was. Though the animated format loses some of the improvisational fun of the classic movie, the guys still get some good licks in.

Memorable Quote:
“I can’t think of anyone who’s benefited more from the death of communism than us.”

52. David Hyde Pierce as Cecil Terwiliger
Episode: “Brother from Another Series”
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In another no-brainer crossover, Pierce played upon his inexorable link to Kelsey Grammer, his brother in Frasier. How convienent it was that Sideshow Bob never mentioned he had a brother, Cecil. Coincidence aside, the pair brought years of experience and a natural chemistry to what would otherwise be just another wacky Sideshow Bob plot.

Memorable Quote:
Bart: “Guess who?”
Cecil: “...Maris?”

51. Robert Goulet
Episode: “$pringfield”
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Believe it or not, before his image was eternally tarnished by a series of Will FerrellSNL sketches, Goulet had a somewhat positive image. Who could hate a guy who sang “Jingle Bells, Batman Smells” at a makeshift casino for kids?

Memorable Quote:
Goulet: “Are you sure this is the casino? I think I should call my manager.”
Nelson: “Your manager says for you to shut up!”
Goulet: “Vera said that? Hmph.”

50. Pamela Reed as Ruth Powers
Episode: “Marge on the Lam”
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You might remember Reed as That One Lady From That Thing, or probably just this episode. She used that unassuming charm as the longtime neighbor, first-time plot point Ruth, who gave Marge a brief Thelma and Louise adventure.

Memorable Quote:
“I should get home to my daughter before that naked talk show comes on.”

49. Neil Patrick Harris as “Bart”
Episode: “Bart the Murderer”
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The only stunt casting more terrible and perfect than Dennis Franz as Homer is a young Neil Patrick Harris as Bart. What’s next? Elle Fanning as Lisa? Katey Segal as Marge? Maybe if we say it enough, it’ll magically appear on basic cable.

Memorable Quote:
‘Tony’: “Bart, I’m scared. Let’s get out of here.”
‘Bart’: “Shut up! Where do you want it, Skinner?”
‘Skinner’: [spits on him]
‘Bart’: “Not smart.” [pumps him full of lead]

48. Alex Trebek
Episode: “Miracle on Evergreen Terrace”
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Before his infamous mustache-shave, Trebek gave a peek inside the seedy underbelly of Jeopardy. It’s not pretty if you lose.

Memorable Quote:
Alex Trebek: “Aren’t we forgetting something, Marge? You were down fifty-two hundred dollars.”
Marge: “But Mr. Trebek—”
Alex: “I asked you before the game if you knew the rules and you said you did. Judges?”

47. Jay Mohr as Christopher Walken
Episode: “Insane Clown Poppy”
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Christopher Walken has never been on The Simpsons, but the producers got something arguably better: Mohr’s Walken impression. In the show we only get a few lines of “Walken” reading Goodnight, Moon. We’d love to see the full thing show up on iTunes someday.

Memorable Quote:
“Please, children, scooch closer. What have I told you… about the scooching?”

46. Ernest Borgnine
Episode: “Boy Scoutz N’ the Hood”
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Even in his earlier years, Borgnine was already America’s grandpa, so it made sense for him to play himself as a boy scout leader. Somehow he fits into Springfield more than most guest stars. Maybe it’s the paunch.

Memorable Quote:
“Hiya! I’m sure you kids know me best as Sergeant Fatso Judson in From Here to Eternity.”

45. George Harrison
Episode: “Homer’s Barbershop Quartet
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Paul McCartney is more famous, and Ringo has more screen time, but there’s something to be said for facilitating one of The Simpsons’ all-time greatest lines.

Memorable Quote:
George: “Hello, Homer! I’m George Harrison.”
Homer: “Oh my God. Oh my God! Where did you get that brownie?”
George: “Over there. There’s a big pile of them.”

44 – 40. The Cast of Cheers
Episode: “Fear of Flying”
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It’s weird to think that when sitcoms end, the lives of the characters keep going, and can even get worse. This is illustrated in the short but impressive cameoganza from Ted Danson, Rhea Perlman, Woody Harrelson, John Ratzenberger and George Wendt. In the segment, Homer steps into the famous bar to find that Norm is a raging, violent alcoholic who has finally lost it. Homer left quickly because he didn’t want to live in that world, and neither do we.

Memorable Quote:
Norm: “Woody, gimme a beer.”
Woody: “I think you had enough, Mr. Peterson. My chiropractor says I can’t carry you home anymore.”
Norm: “Just gimme another beer, you brain dead hick! I’ll kill ya! I’ll kill all of ya!”

39. Buzz Aldrin
Episode: “Deep Space Homer”
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It isn’t often that we get a prestigious member of the scientific community on the show. It comes in handy when you want to portray the true horror of opening a bag of potato chips in zero gravity.

Memorable Quote:
“Watch it, they’re ruffled!”

38. Sara Gilbert as Laura
Episode: “New Kid on the Block”
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A longtime Roseanne vet, Gilbert had experience being the type of girl next door who wears an army jacket. She brings out a lovestruck side of Bart that we don’t see very often, especially with older women. No, we don’t count that fake affair with Edna Krabbapel.

Memorable Quote:
Bart: “How can you like that guy?”
Laura: “I dunno. Maybe because he’s an outlaw. You know that dead body they found behind the mayor’s house?”
Bart: “Jimbo killed him?”
Laura: “No. But he poked him with a stick.”

37. Beverly D’Angelo as Lurleen Lumpkin
Episode: “Colonel Homer”
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You’d probably recognize her as the hot mom in National Lampoon’s Vacation movies, but D’Angelo has a pretty nice set of pipes. She actually wrote and sang Lurleen’s songs in the episode; maybe if Lurleen was that talented, she would’ve aimed her romantic reticule higher than Homer.

Memorable Quote:
Homer: “Guess what, Lurleen. I got you a gig on TV!”
Lurleen: “Oh, Homer! You’re as smart as you are handsome!”
Homer: “Hey! ...Oh, you meant that as a compliment.”

36. Conan O’Brien
Episode: “Bart Gets Famous”
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After jetting out of The Simpsons writers’ room, Conan spared no time in coming back to guest star on the show and rub it in everyone’s face. Whatever happened to that guy?

Memorable Quote:
“Sit perfectly still. Only I may dance.”

35. Harvey Fierstein as Karl
Episode: “Simpson and Delilah“
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Before tackling the issue outright with John Waters, The Simpsons made television history with the first male-on-male romantic kiss ever broadcast. More than just a stunt, Fierstein lent credibility to Karl’s character, and even some ambiguity.

Memorable Quote:
Karl: “You don’t belong here. You’re a fraud and a phony, and it’s only a matter of time until they find you out.“
Homer: “Gasp! Who told you?“
Karl: “You did. You told with me with the way you slump your shoulders, the way you talk into your chest, the way you smother yourself in bargain-basement lime-green polyester.“

34. James Earl Jones as the Narrator
Episode: “Treehouse of Horror I”
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There’s only one man who can give Edgar Allen Poe’s work the gravitas it deserves, and since Gilbert Gottfried wasn’t available, James Earl Jones sufficed. Though Jones doesn’t play an actual character in the Simpson-ized version of “The Raven,” his voiceover was integral, and frankly, unforgettable.

Memorable Quote:
“Once upon a midnight dreary, while I pondered, weak and we—”
Well, you know the rest.

33. Jon Lovitz as Artie Ziff
Episode: “The Way We Was”
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Lovitz has played several of Springfield’s citizens, but the best (and also just the worst) would have to be Artie Ziff, the dorky prom king with an intense libido. In this flashback episode, Homer has to woo Marge away from the technically superior Ziff; Lovitz is so adept at playing slimeballs that you actively root against him in addition to rooting for Homer.

Memorable Quote:
“Marge, I would appreciate it if you didn’t tell anyone about my ‘busy hands.’ Not so much for myself, but I am so respected, it would damage the town to hear it.”

32. Ron Taylor as Bleeding Gums Murphy
Episode: “‘Round Springfield”
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Only appearing in a couple episodes, Bleeding Gums Murphy is one of the most enduring side characters in Simpsons lore. Maybe it was the character’s early death, or Taylor’s gruff but accurate approximation of what everyone thinks every jazz musician sounds like. When Taylor himself passed away, it only solidified Bleeding Gums’ place in the echelon of The Simpsons.

Memorable Quote:
BG: “My friends call me “Bleeding Gums.””
Lisa: “Ew. How did you get a name like that?”
BG: “Well, let me put it this way: you ever been to the dentist?”
Lisa: “Yep.”
BG: “Not me. I suppose I should go to one, but I got enough pain in my life as it is.”

31. Adam West
Episode: “Mr. Plow”
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Before Family Guy came and stretched this cameo into a full-blown recurring character, West’s self-deprecating appearance delighted Batman fans young and old. Since no one had seen his failed pilot Lookwell except know-it-all comedy nerds, his distinctly post-modern sense of humor was a revelation to most.

Memorable Quote:
“Michelle Pfeiffer? Ha! The only true Catwoman is Julie Newmar, Lee Meriwether, or Eartha Kitt. And I didn’t need molded plastic to improve my physique. Pure. West.”

30. Barry White
Episode: “Whacking Day”
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If anyone could pull off the fake guest star by way of pre-recorded music, it would be Barry White. He doesn’t stoop to that level when it came to protest Springfield’s cruel snake-killing holiday, instead delivering some of the goofiest lines ever said in a really sexy way.

Memorable Quote:
“I love the sexy slither of a lady snake.”

29. Kathleen Turner as Stacy Lovell
Episode: “Lisa vs. Malibu Stacy”
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Another guest star with an incredible voice, Turner sounds like she was chain smoking in the womb. She’s perfect as the bitter recluse who created the Malibu Stacy doll, and an excellent cynical foil to Lisa’s unending optimism.

Memorable Quote:
“I may have had things in common with Stacy at the beginning, but thirty years of living her lifestyle taught me some very harsh lessons. Five husbands: Ken, Johnny, Joe, Dr. Colossus, Steve Austin…”

28. Jack Lemmon as Frank Ormand
Episode: “The Twisted World of Marge Simpson”
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Here’s a weird one. Lemmon plays a dopey pretzel salesman, not unlike his character in the film version of Glengarry Glen Ross. At the same time, another Simpson character called Gil is also based on Lemmon’s Glengarry character, but is voiced by regular cast member Dan Castellanetta. If the two met, imagine what would happen! Probably nothing, but it’s interesting to think about. It isn’t, is it? Okay, we can stop here.

Memorable Quote:
“It’s not only not bad—it’s not bread. ‘Knot bread,’ you get it? See?”

27. Stephen Hawking
Episode: “They Saved Lisa’s Brain”
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Everyone knows what Hawking’s computerized voice sounds like, so it wouldn’t have been hard to just plug him into Springfield’s Mensa program without getting him in the studio. Incredibly, that’s exactly what they did. It probably didn’t make a real difference in the performance on the show, but it’s good for getting bumped up a few places.

Memorable Quote:
“I wanted to see your utopia, but now I see it is more of a Fruitopia.”

26. Hank Williams Jr.
Episode: “The Last Temptation of Krust”
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There are a lot of guest stars in “The Last Tempation of Krust,” but Williams blows them all away from offscreen. He’s the voice of the Canyonero, the ridiculous SUV that Krusty the Klown ends up hocking for. Williams’ country-twanged jingle is the catchiest song this side of the monorail.

Memorable Quote:
“She blinds everybody with her super-high beams/She’s a squirrel-crushin, deer-smackin’ drivin’ machine!/Canyonero!-oh whoa!/Canyonero!”

25. Michelle Pfieffer as Mindy
Episode: ‘The Last Temptation of Homer”
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Possibly the most alluring of all of Homer’s near-misses with adultery, Mindy is essentially a buxom female version of the man himself. Obviously Homer decides to stick with Marge, but some lucky guy in Springfield is going to end up with a donut-loving babe who sounds like Michelle Pfieffer when she drools.

Memorable Quote:
Mindy: “Homer? I got a really wicked idea that could get us into a lot of trouble.”
Homer: “Oh, Mindy… we have to fight our temptation.”
Mindy: “No, Homer, let’s do it. Let’s call room service!”

24. Mickey Rooney
Episode: “Radioactive Man”
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Rooney’s appearance in this episode was a little bit like Adam West’s, but somehow even was better. Maybe it was the inflated sense of himself and his box office records. Maybe it was the uplifting speech he gave to Milhouse in an effort to get him to come back to a movie set. But really, it’s probably just him in the Fallout Boy costume saying “Jiminy Jillickers!”

Memorable Quote:
“Jiminy Jillickers! Jiminy Jillickers! Jiminy Jillickers!”

23. Tito Puente
Episode: “Who Shot Mr. Burns?”
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Several musicians have tweaked their work or even created music specifically for the show, but Tito Puente’s Emmy-nominated “Senor Burns” might trump them all. Bless his heart, he even managed to bring back one of Bart’s old catchphrases.

Memorable Quote:
“Aye caramba!”

22. Rodney Dangerfield as Larry Burns
Episode: “Burns, Baby Burns”
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In basically everything he’s ever been in, Rodney Dangerfield plays himself. It’s just that in this episode, he also plays Mr. Burns’ long-lost son. We get all the trademark Danger-isms, all wrapped inside a Mr. Burns-heavy storyline. That’s a combo that deserves respect.

Memorable Quote:
“Wow, this guy is loaded. I mean sheesh. I’ve never seen a guy with a walk-in mailbox. I mean he’s rich. Hey, who am I talking to?”

21. Johnny Cash as Homer’s Spirit Coyote
Episode: “El Viaje Misterioso de Nuestro Homer”
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If you got Johnny Cash to be on your television show, that’s a career-defining moment. If you got Johnny Cash to be on your television show as a mystical/hallucinogenic coyote, complete with recorded growling noises, you should probably just retire on top.

Memorable Quote:
Coyote: “Find your soulmate, Homer. Find your soulmate.”
Homer: “Where? Where?”
Coyote: “This is just your memory. I can’t give you any new information.”

20. Michael Jackson as Leon Kompowski
Episode: “Stark Raving Dad”
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Technically Michael Jackson wasn’t credited with the voice of mental patient Leon Kompowski, but there’s absolutely no mistaking it. Not only did MJ provide a subversive voiceover for a character who’s crazy enough to think he’s Michael Jackson, but he also sang a really sweet song for Lisa’s birthday. It almost makes you forget all the horrible internet comments in any article about Michael Jackson.

Memorable Quote:
“This is my real voice. My name is Leon Kompowski, and I’m a bricklayer from Paterson, New Jersey. All my life, I was very angry. Until one day, I just [Michael Jackson voice] talked like this. [in his normal voice] All of a sudden, everyone was smiling at me, and I was only doing good on this earth. So I kept on doing it. To make a tired point, which one of us is truly crazy?”

19 – 11. The Springfield Isotopes
Episode: “Homer at the Bat”
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Maybe one of the most ambitious guest star rosters ever assembled, “Homer at the Bat” features Major League Baseball legends Roger Clemens, Mike Scioscia , Wade Boggs, Don Mattingly, Jose Canseco, Ken Griffey Jr., Steve Sax, Ozzie Smith and Darryl Strawberry. Each of them is put through a harrowing series of events on Mr. Burns’ stacked baseball team, and incredibly, pretty much every real-life player nailed their role. We’re still wondering if Ozzie Smith ever got out of that dimensional vortex.

Memorable Quote:
Homer: “You’re Darryl Strawberry!”
Darryl Strawberry: “Yes.”
Homer: “You play right field.”
Darryl Strawberry: “Yes.”
Homer: “I play right field too.”
Darryl Strawberry: “So?”
Homer: “Well, are you better than me?”
Darryl Strawberry: “Well, I’ve never met you, but… yes.”

10. Meryl Streep as Jessica Lovejoy
Episode: “Bart’s Girlfriend”
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Meryl Streep is great in everything, including that time she lied to a stranger about not having jumper cables in her car, so it’s not a big surprise that she was stellar (and unrecognizable) as Reverend Lovejoy’s devious daughter. Like a dark mirror of Sara Gilbert’s character, Bart is infatuated with Jessica, but in this case she manipulates him to her own end in a way only Streep can.

Memorable Quote:
“Because, if you tell, no one will believe you. Remember I’m the sweet, perfect minister’s daughter… and you’re just yellow trash.”

9. Mandy Patinkin as Hugh
Episode: “Lisa’s Wedding”
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In yet another mind-blowing voicing credit, Mandy “Inigo Montoya” Patinkin plays the prissy Hugh in the future-set episode. As the charming, intelligent Hugh Grant-esque love interest of Lisa Simpson, Hugh is a perfect encapsulation of what makes Lisa different from the rest of her family. She eventually dumps her beau when she realizes he’s a perfect man without a heart. The moral of the story: There’s always a chance for Milhouse.

Memorable Quote:
“I must say, you were right. This has been quite trying. You know, I’ve attempted to enjoy your family on a personal level, on an ironic level, as a novelty, as camp, as kitsch, as cautionary example… nothing works.”

8. Patrick Stewart as Number One
Episode: “Homer the Great”
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Here’s a voice you can’t mistake for anyone else’s. Stewart’s stern poise elevated the leader of the Mason-like Stonecutters to another level. That same steely tone also works wonders for beer jokes.

Memorable Quote:
“Welcome to the club, Number 493. You have become a member of the ancient and noble society of Stonecutters, who since ancient times have always endeavored to shatter the stone of ignorance, to bring forth the light of truth… now, let’s all get drunk and play Ping-Pong!”

7. Glenn Close as Mona Simpson
Episode: “Mother Simpson”
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In between all the cultural references and fat jokes, The Simpsons has been known to have quite a few tearjerkers. One biggie in particular came in the form of Homer’s mother Mona, played with a gentle touch by Close. Though she was absent for years, Close made you believe in her character’s fugitive tale, and in her love for her son and grandchildren.

Memorable Quote:
“Homer, don’t be so hard on little—what is his name?”

6. Dustin Hoffman as Mr. Bergstrom
Episode: “Lisa’s Substitute”
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Another not-so-secret uncredited guest star, Hoffman won tons of praise as Lisa’s compassionate substitute teacher, Mr. Bergstrom. A schoolgirl crush was an inevitable storyline for Lisa; if they were going to do it, it might have well been with an Oscar-winner.

Memorable Quote:
“And, for the record, there were a few Jewish cowboys, ladies and gentlemen. Big guys who were great shots and spent money freely.”

5. Leonard Nimoy
Episode: “Marge vs. the Monorail”
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Though he’s been featured in other places in The Simpsons canon, nowhere else was Nimoy utilized better than in the infamous Conan O’Brien-penned “Marge vs. the Monorail.” Equal parts stirring and silly, Nimoy set the bar for great guest stars that sort of just stand around and react to things.

Memorable Quote:
Leonard Nimoy: “My job here is done.”
Barney Gumble: “What do you mean? You didn’t do anything.”
Leonard Nimoy: [chuckles] “Didn’t I?”

4. Dave Thomas as Rex Banner
Episode: “Homer vs the Eighteenth Amendment”
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To some he’s known as “Mr. F,” but to most other God-fearing Americans, Dave Thomas is Rex Banner: Prohibition Agent. Active for the short period that Springfield thought it was a dry city, Banner was relentless in his pursuit of the elusive “Beer Baron.” Though Banner was thrown from a catapult before he could jail his man, rumors persist that the Beer Baron was one Homer S. Wait, that’s too obvious—let’s call him H. Simpson.

Memorable Quote:
Rex Banner: “Listen, rummy, I’m gonna say it plain and simple. Where’d you pinch the hooch? Is some blind tiger jerking suds on the side?”
Barney Gumble: “Yes…?”

3. James Woods
Episode: “Homer and Apu”
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The quintessential self-parodist on The Simpsons, James Woods struck a balance between likeability and frenzied mania as he took over the Quik-E-Mart to study for a movie role. His B-plot was really unnecessary to Apu’s redemption after losing his job, but it gave us the best animated microwave-cleaning scene ever drawn.

Memorable Quote:
“Tony, you’re my agent. You have to do something about this… How can it be the same movie if they’ve changed my character from a convenience store clerk to a jittery eskimo firefighter? Uh huh… uh huh… mm hmm… well, actually, that’s a pretty good explanation. Now this is gross, right, this’ll be gross points in this new…? OK. Yeah, ‘cause there’s monkey—yeah, OK, great. OK, good: book me a flight, rent me an igloo, and tell those dorks at the Kwik-E-Mart that boom! I am outta here, I’m a dot, I’m gone, OK? What do you mean, I gotta give two weeks’ notice? Why you frickin’, no good, motha$%^&@ &!$@# cheese! No, not you, I’m just talking to my oven.”

2. Albert Brooks as Hank Scorpio
Episode: “You Only Move Twice”
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Yes, Albert Brooks is on this list two times and yes, he deserves it, no question. Part supportive manager, part James Bond archnemesis, Homer’s new boss Hank Scorpio is a true original. The pair’s hilarious rapport is beautifully set against the backdrop of a supervillain lair, and the visual gags are second to none. Watching this episode will make you a better person, and actually increases your chances of finding $20 in your pocket.

Memorable Quote:
Hank Scorpio: “Hey, look at my feet. You like those moccasins? Look in your closet; there’s a pair for you. Don’t like them? Then neither do I!” [throws shoes] “Get the hell outta here! Ever see a guy say goodbye to a shoe?”
Homer: “Heh-heh. Yes, once.”

1. Kelsey Grammer as Sideshow Bob
Episode: “Cape Feare”
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Some might consider this cheating, but Sideshow Bob is too great a character to settle for anything less than the top spot. Grammer eviscerates every shred of scenery in every scene he’s in, and especially in “Cape Feare,” he never misses a note in his quest to finally destroy Bart Simpson.

Memorable Quote:
Bob: “Well, Bart…any last requests?”
Bart: “Well, there is one, but…nah.”
Bob: “No, go on.”
Bart: “Well, you have such a beautiful voice.”
Bob: “Guilty as charged.”
Bart: “Uh huh. Anyway, I was wondering if you could sing the entire score of the H.M.S. Pinafore.”
Bob: “Very well, Bart. I shall send you to heaven before I send you to hell.

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