Over its long (and still mostly illustrious) history, one of the many things The Simpsons has excelled at is its selection and use of guest stars.
Though their impact has perhaps diminished over recent years, which seems to correlate with the general direction the show’s quality has taken, The Simpsons still has some pretty good drawing power.
For the purposes of making the list a little easier to pick, no-one who appeared playing themselves has been allowed in. There’s also the fact that these kinds of performances rarely seem to feature in truly classic episodes. (Disagree? Feel free to leave a comment below.)
Before we start, an honourable mention must surely go to brilliant Drive and Finding Nemo star Albert Brooks, who has guested in multiple episodes, as well as The Simpsons Movie, and has been excellent in every single one (especially as Hank Scorpio in You Only Move Twice). Sadly, he was just edged out by the star power below but, if you’re so inclined, listen to the commentary for any of his episodes to hear just how much the production team appreciated his every performance.
Now, on with the Top 5…
Harvey Fierstein as Karl in Simpson and Delilah
Simpson and Delilah is only the fifteenth episode of The Simpsons ever and so Fierstein’s performance would be a strong contender for being one of the first big name stars the programme attracted, even if the episode wasn’t brilliant – which, thankfully, it is.
Fierstein (perhaps best known for the marvellous Torch Song Trilogy and his appearance in Mrs. Doubtfire) lends his trademark gravelly tones to play Homer’s assistant, Karl, in what would turn out to be a surprisingly nuanced and touching role as a man who has complete faith in the bumbling patriarch.
Plus, it featured a man-on-man kiss a whole decade before the official ‘first’ homosexual smooch on network TV in Dawson’s Creek.
Michelle Pfeiffer as Mindy Simmons in The Last Temptation of Homer
You’ll notice that most of the episodes featured here have something of an emotional core to them, but this one was just out-and-out hilarious.
Singing trout, trying to think unsexy thoughts, the bellhop’s insinuations about what one might do with a king-size bed, these are just a few examples of the episode’s extraordinarily high gag rate, back when the series could do that and still maintain a coherent plot.
But there’s a softer side to the episode as well, when Homer, despite temptation, reaffirms his love for his life (even if it was partly motivated by the finding of a turkey behind the bed). Pfeiffer does surprisingly well as the co-worker temptingly similar to our hero, and she manages to pack a lot of warmth into the performance, especially in her goodbye scene.
Dustin Hoffman as Mr. Bergstrom in Lisa’s Substitute
And we’re right back to the fuzzy, warm episodes. Lisa’s Substitute is a great big hug of an episode that’s a wonderfully poignant pivot for often unfairly-overlooked Simpson family member, Lisa.
Hoffman (using the pseudonym ‘Sam Etic’; more on that later), plays substitute teacher Mr. Bergstrom, who has a profound influence on her during his brief time at Springfield Elementary.
This episode packs a lot of important stuff in: there’s a strong message for Lisa culminating in the unforgettable ‘You are Lisa Simpson’ note, there’s some ruminations on loss after he leaves, and we also see Homer develop and really come through as a father. It fits all this in, but never feels too sappy. Throw in a great parody of The Graduate, and you have another early classic.
Glenn Close as Mona Simpson in Mother Simpson (and others)
We’re mainly focussing on that episode here, as later appearances of Mona have provided somewhat diminishing returns.
Mother Simpson came about when writer Richard Appel realised than amazingly no episode had been made about Homer’s mother, and a classic episode, funny and moving in equal measures, was born. If you didn’t at least tear up at the ending, then you must be made of pretty strong stuff.
The challenge for any actress playing Mona would be to make the audience very quickly care about a character who, although important, we hadn’t really met before and Close pulls it off with aplomb, which just makes the ending even more heart wrenching.
Fun fact: the ‘D’oh!’ as Mona leaves was actually recorded by Simpsons regular Pamela Hayden, as Glenn Close was reportedly unable to deliver the line properly.
Michael Jackson as Leon Kompowsky in Stark Raving Dad
Arguably the biggest celebrity ever to appear on the show. And yes, that really is him, under the alias ‘John Jay Smith’ (when Lisa says that Jackson and Dustin Hoffman both appeared in the Itchy & Scratchy Movie without using their real names, she is clearly making a sly reference to both of their appearances on The Simpsons).
Gentle giant Leon Kompowsky is actually played by three people in this episode: Michael Jackson does indeed provide the speaking voice, but due to contractual obligations Kipp Lennon does all the singing. Finally, regular cast member Hank Azaria supplies Leon’s ‘real’ voice.
That piece of trivia is almost enough to earn Jackson’s place on this list alone, but it’s not a bad episode all round; ‘Happy Birthday Lisa’ is a lovely little moment, and it comes from an era when the show was just beginning to hit its best.
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Who’s your favourite ever guest star? Let us know below…