Top 20 Guest Stars On “The Simpsons”

by | May 15, 2009 at 11:47 AM | Best Of The Guests

A guest starring role on The Simpsons is considered one of television’s highest honors. If you’re on it, you’ve made it in show biz. Especially if you play yourself.

For the show’s executive producer Al Jean, the rewards are sweet. As he put it in an interview with Fancast, “Having guest stars on the show might be the most exciting and unexpected part of working on The Simpsons…to work with these people. You admire their work and then you get to work with them.” The one problem? Not everyone wants to be a Simpsons star. Jean confessed that they’ve received a steady stream of “no’s” from every U.S. President asked to appear, but he admits they’re still holding out hope for one President in particular: Barak Obama. In fact, a script is currently in the works for the standing Commander In Chief, Jean said.

Every season the Fox comedy seems to out-do itself with a new roster full of impressive talent. This past season everyone from Anne Hathaway, Julia Louis-Dreyfus, Jodie Foster, Emily Blunt, Ellen Page, and Denis Leary loaned his or her voice to the series with predictably hilarious results. As the animated hit wraps up its 20th season this Sunday, we’ve compiled a list of the 20 most memorable guest stars through the years. In our best Troy McClure impression: “You may remember them from such shows as…The Simpsons.”

1. Phil Hartman
The consummate voice actor, Phil Hartman first appeared as the voice of shifty lawyer Lionel Hutz, but was best known for voicing the egocentric B-movie actor Troy McClure. Before his untimely death in 1998, Hartman was considered by the creators of The Simpsons to be an unofficial cast member, and proved it by calling on Hartman for the voice of several other memorable characters like crooked monorail salesman Lyle Lanley.

2. Kelsey Grammer
Playing Dr. Frasier Crane for over 20 years, Kelsey Grammer is no stranger to TV fans – or to the Emmy’s. He’s been nominated 16 times and has won 5 statuettes, mainly for his work as the urbane psychiatrist on 4 different shows that included or starred the character. But it was his win as “Sideshow” Bob Terwilliger on The Simpsons that fills him with the most pride. Said Grammer after winning the Emmy for best voice-over in 2006, “I’m delighted that my work as Sideshow Bob has been recognized and I’m indebted to Matt Groening, James L. Brooks and Sam Simon for giving me the job. It’s some of the easiest work I’ve ever done, since Sideshow is basically Frasier Crane dipped in arsenic.” Killer.

3. Jon Lovitz
Best known as “Tommy Flanagan, The Pathological Liar” (the character who memorialized the catchphrase, “Yeah! That’s the ticket!”) on Saturday Night Live, Jon Lovitz has always been known for his distinctive vocal talents. Those skills have earned him a lucrative career as a voice actor and it all started on The Simpsons when he played Marge’s ex-prom date Artie Ziff. After that role, Lovitz starred on his own show, The Critic, a darling of fans and reviewers alike. With that show’s untimely demise, Lovitz has appeared regularly on The Simpsons as theater director Llewellyn Sinclair, paparazzo Enrico Irritazio, Professor Lombardo and Aristotle Amadopolous. In a nod to his beloved Jay Sherman, producers brought back the character in the crossover episode A Star Is Burns where his penchant for panning definitely rubbed Mr. Burns the wrong way. Shoulda learned how to lie a little.

4. Kiefer Sutherland
The Simpsons celebrated its 399th episode by creating a hilarious parody of another FOX hit, real-time drama 24. The episode entitled 24 Minutes featured Sutherland playing “himself,” the hard-ass CTU agent who never sleeps, Jack Bauer. Despite showing a clear talent for comedy in films (most notably as the harried FBI agent in Flashback), Sutherland is most comfortable playing the heavy. “Comedy is not something innate in me. I don’t have that kind of gift. And, to my own detriment, I get quite self-conscious quite quickly, which a comedian cannot have,” he said.

5. Tony Blair
Tony Blair? That’s right. THAT Tony Blair. In The Regina Monologues, Bart takes the family to London, just to get Marge out of the house, but Homer ruins the vacation when he drives a car into the Queen’s horse-drawn carriage. Scoring a Prime Minister was a major coup for the series (the only other politician so far was then Presidential candidate Rudy Giuliani) and Al Jean remembered that Blair “made it very clear that he was only interested in doing the show if he could promote tourism in Britain.” Hoping for the best, Jean took a chance and while in London promoting the 300th episode he received a call stating, “if you go over to Downing Street tomorrow and can promise to get the recording done in 15 minutes, then the Prime Minister will do it.” Jean was “so nervous, it was ridiculous” when he met Blair, an event he has cited as “one of the most fantastic moments of my life.” Talk about your 15 minutes of fame… barely enough time for a spot of tea. But plenty of time to immortalize a friend from across the pond.

6. Michael Jackson
Michael Jackson guest starred on The Simpsons in the bizarre (even for The Simpsons) episode Stark Raving Dad. He voiced Leon Kompowsky, a deluded character who believed he was the real Michael Jackson. Due to contractual conflicts, he was credited under the name John Jay Smith and penned the tune from the show “Do the Bartman” which became something of a cult hit at the time. Cool Simpsons Trivia: Because of the misleading credit, the fact that it was actually MJ remained a rumor among fans until Matt Groening confirmed it really was Jackson when the episode was released on DVD in 2003. Hey Michael, haven’t you learned by now? Some secrets should never be revealed.

7. Dustin Hoffman
Hoffman played Mr. Bergstrom in Lisa’s Substitute. What’s with these Hollywood contracts that prevent stars from getting credit? Hoffman is listed as Sam Etic in a nod to his Jewish heritage. Again, the rumor mills swirled for years after the episode until Hoffman himself confirmed the truth. Later, Lisa Simpson makes fun of the pseudonym trend in a season four episode when she says “Dustin Hoffman and Micheal Jackson used fake names, but you could tell it was them” as she and Bart walk out of a movie theater. The film? “Itchy & Scratchy: The Movie.” Wonder who played Itchy?

8. Joe Mantegna
Mantegna has a recurring role as the voice of mob boss Anthony “Fat Tony” D’Amico. Famous as a man of few words, Mantegna nonetheless insists on voicing the character himself, no matter how little dialogue the character gets. Good move. Before his death, Phil Hartman stepped into the role on one occasion in the episode A Fish Called Selma because Mantegna was out of the country filming a movie. Never again. As Tony puts it, “If Fat Tony sneezes, I want to be there.” And what Fat Tony wants, Fat Tony gets.

9. Albert Brooks
Albert Brooks has been a frequent guest voice on The Simpsons since the first season, when he appeared as “RV Bob.” In another credit listing quirk, the multi-talented actor, writer, director and comedian (whose real name is Albert Einstein!) is always billed as “A. Brooks.” In the beginning Albert Brooks was credited in the “also starring” section until season 8, where he was elevated to “Special Guest Voice” status for his portrayal of Hank Scorpio in You Only Move Twice. Knowing a good thing when they hear it, the producers hired Brooks to voice Russ Cargill in “The Simpsons Movie.” Genius.

10. James Woods
Real star power is when you appear on The Simpsons as yourself, and Woods did so in the episode Homer and Apu. Researching an upcoming film role, Woods is hired to replace Kwik-E-Mart owner Apu after Homer reveals some shady meat selling practices at the store. Billed as one of the funniest episodes of all time, Woods has seen the value of lampooning himself. In fact, the boost to his career worked so well, he’s done the same thing several times on Family Guy, even lending his name to the hometown Rhode Island high school that Chris and Meg attend. Woods is thus forever immortalized as the self-centered actor with a sweet tooth. Ooh! Piece of candy!

11. Ron Howard
Howard appeared as himself on two different episodes of The Simpsons. In When You Dish Upon a Star, “Opie Cunningham” pitches Homer’s movie idea and gets it greenlit. And in Hello Gutter, Hello Fadder Homer and Howard fight each other during taping of the show “The Springfield Squares.” Famous for happy endings, Ron Howard convinces Homer to spend more time with the kids and even gives him some money for a first-class outing, a la Happy Days. In a memorable fadeout, Howard’s darkly comedic side is revealed when Howard “yoinks” the money back from Homer as he drives back to Hollywood. Where’s Barney Fife when you need him?

12. Denis Leary
Described as a “very epic” superstar in Lost Verizon Denis Leary loses his famous temper at a celebrity golf tournament and throws his cell phone in anger. Of course Bart finds it and makes some prank calls, imitating Leary. The kicker is when Bart accepts a role for Denis in Brian Grazer’s big-screen adaptation of “Everybody Poops” – and does a better job! Denis is in fine form in this episode, pulling a few memorable rants over the phone. As he says, “I will not bond. I will not share. I refuse to mature.” Bart when he grows up?

13. Danny DeVito
Danny DeVito plays Homer’s half-brother Herb Powell, who, unlike Homer, grew up and made something of himself – twice. When the two meet for the first time, Herb is a billionaire car maker. Trusting too much in family, Homer naturally causes Uncle Powell to lose all his money. The next time DeVito guests, he invents a baby talk translator and regains his wealth. DeVito clearly relishes the part, playing it with all the gusto we’re accustomed to from the pint-sized comedic actor. Louie’s come a long way.

14. Kim Basinger & Alec Baldwin
Filmed when the Hollywood Power Couple were still an item, “When You Dish Upon a Star” this twofer finds the movie stars looking to Springfield for a break from the grind of celebrity. Hiring Homer as a personal assistant proves unwise when he blows their cover to the town. In the episode, Basinger is the big star. How ironic life can be. These days, Kim is barely a blip on the radar and thanks to 30 Rock, Alec Baldwin is back on top.

15. Spinal Tap
The Otto Show featured the fictional super group visiting Springfield on tour. Ever the tragic power trio, the drummer is killed by an onstage prop. Only this time, the rest of the band follows suit when their tour bus flies off a cliff. Harry Shearer pulls double duty as a band member and several other characters he regularly voices. Voted one of the best episodes ever by rabid Spinal Tap fans, the legend endures. On a scale of 1 to 10, this episode goes up to 11.

16. Stephen Hawking
The paralyzed Physics genius is handled with kid gloves on The Simpsons, unlike the lambasting he gets on Family Guy. Despite a world renowned reputation prior to his appearance, relatively few people had heard of the professor, called “the smartest man in the world” in some quarters. That all changed after They Saved Lisa’s Brain aired. As Hawking himself admits, “more people recognize me for my role on The Simpsons than they do for the science.” Did America actually learn something from the show? Ugh, don’t make us think!

17. Jerry Springer
Jerry gets his just desserts when Homer and Marge appear on The Jerry Springer Show in an attempt to discover who Maggie’s real father is. Maggie ends up killing Jerry at the end of the show before the secret can be revealed: Maggie was fathered by the alien Kang! Maggie also speaks in an alien voice during the skit. So many taboos broken in one show? Of course, it’s all fantasy when we realize it’s part of the fabled Treehouse of Horror annual Halloween episode. Too bad. We were really getting used to the idea of the last of Jerry’s “Final Thoughts.”

18. Britney Spears
How does the biggest star in the world rehab herself after falling off the top of the heap? For Britney Spears, the first step of the comeback tour she’s on right now started when Maggie imitated the pop tart from her “Baby One More Time” video. Apparently, despite a reputation for treating celebrities like mere mortals, the writers went easy on the Britster. Said Yeardley Smith (Lisa Simpson) at the time: “Britney is ripe for the picking. But we have to do it well – we don’t want to be cruel.” OK. It’s time for a rematch. This time, take off the gloves.

19. Elizabeth Taylor
When an earth shattering event like Maggie’s first words are spoken, only the most well known woman in the world will do. Naturally, the producers wanted Elizabeth Taylor for the job. As expected, the episode Lisa’s First Word caused quite a stir. But not for the reason you might think. Feminists everywhere were outraged that Maggie’s first word was “Daddy” but they would have been much more offended had they been at the taping for the scene. Matt Groening told Playboy in an interview that the single word required 24 takes, each one considered too sexy by the writers and the director. After the last one, Taylor stood up, said “F*** you” and walked out. Maggie’s growing up fast!

20. Amy Poehler
The Parks and Recreation star wasn’t always one of the hottest comedians in the world. In 2004 Amy played Jenda in the episode Future-Drama, a spoof of the competing (barely) series Futurama. Since then she’s been on a whirlwind tour to the top of the TV ladder and even dabbled in movies with pal Tina Fey in Baby Mama last year. But Amy is the first to admit that being on The Simpsons is something special. Says Amy, “I’d been a cast member on SNL since 2001 so I knew my way around a recording studio. But nothing made me realize I’d made it more than doing a guest voice on The Simpsons.”

Here’s to 20 more years!

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