This is the first in a five part daily segment leading up to Friday’s release of The Simpsons Movie.  As the resident Simpsons geek of the blog (and of my high school, and most likely town), I hope to provide an educated look back on the single most important piece of media in my lifetime.  And I also hope to avoid falling into creating the same lists that every other site on Earth is doing this week.  All quotes/episode numbers/details are from the invaluable Enjoy!

(Note:  I gave Glenn the idea of putting a repeating italicized intro to his running segment, so don’t act like I’m ripping him off with this. If anything, he’s ripping me off retroactively.)

What defines a Simpsons guest star?  There are plenty of criteria that I have to take into account to make this list — for example, is one still a guest star if their character reoccurs more than twice?  In my opinion, “Short answer yes with an if, long answer no with a but.” Here is who will be left out of the list because they appeared too many times:

  • Phil Hartman — If he were allowed to be on the list he would be the outright #1.  Both Lionel Hutz and Troy McClure are painfully funny every time they appear on screen, and if they weren’t on so many episodes it would make this list a whole lot easier for me.
  • Kelsey Grammer — And here’s who would be #2.  Sideshow Bob is a brilliant creation, and Grammer voices him perfectly. But he is just a little too frequent to be considered a guest.
  • Frank Welker — You may not know this name, but you should.  He is the voice of almost every single animal, not just on The Simpsons, but on every cartoon EVER.  Unless an animal clearly has the voice of Dan Castlenetta, it’s Frank.  He’s been on a ton of episodes, though, so I can’t include him.
  • Marcia Wallace — The voice of Edna Krabappel, she is technically a guest star.  But not really.
  • Joe Mantegna — Fat Tony is a wonderful creation, and he would be way up there, but he’s far too frequent.

As with any Simpsons list, I’m sure every single choice will be debatable and there are 5 worthy alternatives for each spot on the list.  But enough weaseling, let’s get down to it!

10. The Beatles (minus John)

Can you believe I started out the list with a cop-out?  Every one of these guys were good on their own, but putting the three together demonstrate the power that The Simpsons really carries.  Here’s the most famous band of all time, arguably, and this show manages to get every living member of it to appear as themselves and even poke some fun.  In Lisa The Vegetarian, Paul McCartney taught Lisa that it was OK to be a vegetarian even if her family didn’t agree with it, in a scene steeped with Beatles references.  In Homer’s Barbershop Quartet, George Harrison only had a few lines, but one of them is among my favorite; After introducing himself to Homer, Homer is overwhelmed not by whom he’s talking to, but by the brownie he’s holding.  After Homer runs away to devour a pile of them, Harrison just smiles and obliviously says “Well, what a nice fellow.”  Finally, we have Ringo Starr in the second season episode Brush With Greatness.  We learn that Marge was obsessed with painting Ringo’s face, and that Ringo is determined to answer every piece of fan mail he receives by hand, even if that means he’s 30 years behind.  While none of these are too brilliant on their own (Paul’s is the funniest), they are perfect examples of the incredible star power The Simpsons has.

9. Ron Howard – Himself

Ron Howard certainly doesn’t have the star power that The Beatles do, but his cameos are the funniest examples of guest appearances on the “new” episodes.  In When You Dish Upon A Star, Homer mistreats Howard constantly, calling him Potsie and Horshack.  They also portray him as an alcoholic moocher who doesn’t have his own place to stay and has no athletic ability.  And he steals Homer’s idea for a film about a killer robotic driving instructor who travels back in time for some reason and has a best friend who’s a talking pie, called “The Terminizor: An Erotic Thriller.” It’s not brilliant voice work or anything, but it was definitely a highlight in a pretty rough span of time.

8. Stephen Hawking – Himself

The greatest scientific mind of our lifetime is a Simpsons fan.  Hawking, the world-renowned author and physicist, has publicly stated that The Simpsons is his favorite TV show of all time (how’s that for a ringing endorsement?), and he backed up that statement by appearing on the show twice.  He busts in when Springfield’s Mensa chapter has some trouble, brags about his incredible IQ, and even makes some jokes about his artificial voice and multi-functioned chair.  And, of course, he steals Homer’s theory of a donut-shaped universe.  If you’re that smart, you have to be able to laugh at yourself.  Hawking does this and then some, and his appearances are some of the best.

7. Johnny Cash – Space Coyote

Just the mere fact that I’ve written that above title should be enough to give him this spot.  One of our most serious, well respected American songwriters tells Homer that they key to happiness is getting more possessions (“You don’t even own a computer!”) and then gnaws on his leg.  And through all this, he is a psychedelic space coyote that Homer only sees because he is hallucinating. Now THATS the magic of cartoons!

6. Leonard Nimoy – Himself

Leonard Nimoy is a legend in the pantheon of sci-fi, and knowing Simpsons writers have a flare for the nerdy, they probably never dreamed that they would get such a great performance out of him — not once, but twice.  First, in the classic episode The Springfield Files, Nimoy plays a host of a show that investigates the paranormal, and leads in with this gem: “Hello. I’m Leonard Nimoy. The following tale of alien encounters is true. And by true, I mean false. It’s all lies. But they’re entertaining lies. And in the end, isn’t that the real truth? The answer is: No.”  He then travels to Springfield to be involved in the story himself, and while there enjoys a hot dog.  Nimoy’s other appearance comes in an even more brilliant episode, Marge vs. the Monorail.  He pokes more fun at himself this time, prompting his neighbor on the monorail to ask “Does anyone want to switch seats?” and, when he asks Mayor Quimby if he even knows who he is, gets the response “I think I do, weren’t you one of the Little Rascals?”  And at the end, of course, he beams out.

5. Dustin Hoffman (credited as Sam Etic) –  Mr. Bergstrom

Lisa’s Substitute — the first episode to really present the entire Simpson family as humans with faults and feelings and emotions, it ventured into heartbreak, legitimate family strife, and loss.  It also presented the most vulnerable portrayal of Lisa in the show’s entire run, and it had a solid funny B story.  All of this goodness was anchored by mystery guest star Sam Etic, who was clearly Dustin Hoffman to anyone with a pair of ears (and maybe to some people with only one).  Throw in the multiple references to The Graduate (“Ms. Krabappel, you’re trying to seduce me.”) and the need for a pseudonym really just escapes me.  Nevertheless, his performance here is both funny and emotional, the perfect example of how good The Simpsons could be early on in the run.

4. Michael Jackson (as John Jay Smith) – Leon Kompowski

Before Michael Jackson was all gross creepy, he was a pretty good singer.  And he had an OK sense of humor, too.  He was probably still crazy back then (yet another user of a silly nom de guerre), but he shined in this episode, as a raceless weirdo simultaneously playing “the big white guy who thinks he’s the little black guy.”  Jackson was pretty funny and did well in his role of helping Homer feel better about himself, but the real strength of this appearance was showing the awesome star power that The Simpsons could get.  Michael Jackson was a social recluse and an international phenomenon at the same time, and somehow a cartoon with only two seasons under its belt got him to carry an episode.

3. Jon Lovitz –  Artie Ziff, Professor Lombardo, Aristotle Amadopolis, Llewellyn Sinclair, Jay Sherman

God bless Jon Lovitz.  If you didn’t know, he recently got into a scuffle with Andy Dick.  Dick, who Lovitz has been at odds with for some time now, made a joke about the death of his close friend Phil Hartman.  And Lovitz did the only thing that he could have, he beat the crap out of Andy Dick.  Moving past that, Jon Lovitz was one of the big two guest stars in the show’s early run (don’t worry, the other one is still coming).  He played a variety of characters and played them all to perfection.  In case there is some confusion, Lombardo is Marge’s art teacher, Amadopolis is the owner of the Shelbyville Nuclear Power Plant, and Llewellyn is the director of Springfield’s incredible performance of A Streetcar Named Desire.  Artie Ziff is a great recurring role, and Jay Sherman is The Critic, who came over in Matt Groening’s least favorite episode of all time.  Lovitz is a great comedian who really helped The Simpsons get off it’s feet early on.

2. John Waters – John

The second-best single episode performance of any guest star.  Waters didn’t just make an on-screen appearance or a brief cameo, he carried a brilliant episode with a really strong message.  In Homer Phobia, Homer becomes friends with a man named John who he later learns is gay.  Suddenly afraid of him, Homer wants his family to have nothing to do with John, even though he’s the best thing that has ever happened to him.  John stays nice throughout, saving Homer in the end, and winds up being one of the funniest characters ever.  He also opened the door for a real pig-headed side of Homer that everyone had assumed before but that had never really been shown, and also sparked a moral debate on the show.  Even disregarding the social importance of Waters’ appearance, it is still funny enough on its own to earn it this spot.

1. Albert Brooks – Hank Scorpio(!), Brad Goodman, Jacques, Cowboy Bob

Brad Goodman was very funny as a self-help guru, and Jacques brought up some great drama to show the show’s range early in the run, but nothing (and I mean nothing) will ever compare to Hank Scorpio. The greatest single-episode character of all time, on any TV show, is Scorpio.  He’s the nicest man you’ve ever met.  Don’t like the moccasins that are waiting for you upstairs in the closet?  Then neither does he!  Want some hammocks for the work place?  He thinks it’s a great idea!  Of course, then he blows up the 59th street bridge while threatening to blow up the world.  What is it exactly that they do over there in Cypress Creek?  It doesn’t really matter when you have a boss that will tell you that you must do what’s best for your family before taking a flame thrower to a platoon of soldiers.  Please, please, watch You Only Move Twice.  Buy the season 8 DVD if you don’t already have it.  And maybe if you support Project Arcturus, you’ll get your own football team.  It might not be the Dallas Cowboys, but it’s a start.

So there you have it.  After hours of deliberation, I feel these are the greatest guest stars in Simpsons history.  Coming tomorrow:  Another Simpsons list of some sort!