The 100 Greatest Simpsons Guest Stars

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20. Michael Jackson as Leon Kompowski
Episode: “Stark Raving Dad”

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”

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”

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”

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”

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”

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”

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”

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”

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”

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”

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”

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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