Our Top Ten Favorite "The Simpsons" Stars

Before the days of pandering for audiences with Britney Spears and Backstreet Boys, “The Simpsons” had a knack for casting humongous and iconic stars for their series to come on and play important roles. And then later on they’d lampoon them. There was Michael Jackson, and Jack Lemmon, and Jon Lovitz, as well as most of the Beatles. And while it never became the main lure for audiences, it was a treat to see who’d pop up in the next episode to play a role in the Simpsons’ lives. Here are ten of our favorite guest stars on “The Simpsons.”

James Woods as Himself
(Homer and Apu)
Before “Family Guy” came on board and told audiences “Hey look at how insane and crazy James Woods is! Isn’t that funny?!” The folks at “The Simpsons” did it first, they did it best, and had the foresight to show audiences how loony Woods can be by giving him the best guest spot on “The Simpsons” of all time. And they didn’t have him on thirteen times with his same shtick becoming a rival with two unfunny main characters. Nope. James Woods was a maniacal Hollywood stalwart who just happened in to Springfield to meet most of our Simpsons gang engaging in a surreal world where he fit just fine. Oh and in case you were wondering, they also lampooned Adam West first as well. And they did it better.

Dustin Hoffman as Mr. Bergstrom
(Lisa’s Substitute)
One of the earlier episodes of “The Simpsons” that focused more on heart than wacky hijinks, Lisa finds a soul mate in her substitute teacher, a very charming Jewish educator named Mr. Bergstrom. Credited as Sam Etic, legendary actor Dustin Hoffman is a man who recognizes the magic in Lisa, immediately and in effect helps Homer appreciate what kind of amazing daughter he has on his hands. Though Lisa can’t face Bergstrom leaving her life, he imparts some golden wisdom and changes her life forever. It’s a touching episode and one that Hoffman sells with his usual skill.

Michelle Pfeiffer as Mindy Simmons
(The Last Temptation of Homer)
Shockingly one of the many times in Homer’s life where he’d be tempted to have an affair, Homer is met with Mindy Simmons, a co-worker at the plant who is gorgeous, charming, and happens to be the female counterpart to Homer. Mindy recognizes the sexual appeal of Homer, and the two form a very tension filled relationship that could easily fall in to a sexual relationship if they’re not careful. What makes things worse is Homer has a fantasy about what it’d be like if he never married Marge and married Mindy, and he is oddly better off. In either case, love wins out, but Pfeiffer has a good time making her own Homer of the show.

Mel Gibson as Himself
(Welcome to Blunderdome)
Okay, so what if Mel Gibson is a drunken anti-semitic Christian religious fanatic with a martyr complex who probably beat his girlfriend and threatened her with a gang rape by black guys describing them with the N word, whose father has a background with the Nazis, who bears an uncomfortable fixation on the Three Stooges? I still really enjoyed his movies, and all things considered, his guest spot on in “Welcome to Blunderdome” is comedy gold with tips of the hat to the Three Stooges, and Mr. Smith Goes to Washington. As we’ve seen time and time again, Homer and Hollywood simply don’t mix, and Gibson is left trying to re-build his career once he’s decided meeting Homer was a big mistake.

Danny DeVito as Herb Powell
(Oh Brother, Where Art Thou?, Brother, Can You Spare Two Dimes?)
The Saga of Herb Powell is a fascinating one. When Homer first meets his long lost orphan brother, he realizes he’s exactly like him. Except with a head of hair, skinny, and incredibly successful. But Herb is longing for a family in spite of his mass success in the auto industry. Herb and Homer’s relationship makes for a sweet and funny bit of familial bonding and, Homer being Homer, he manages to basically ruin Herb Powell’s career creating “The Homer,” the perfect car.
Herb returns from a long bout of hating his brother in “Brother, Can You Spare Two Dimes?” where he builds a machine that can decipher baby talk to tell adults what infants and newborns need. Of course Homer more than repays his brother by not punching him out every five minutes and giving him his beloved vibrating chair. Devito is wonderful as Powell and it’s a shame we only saw him with the Simpsons twice in the whole series.

Phil Hartman as Troy McClure
(The Simpsons)
When the late great Phil Hartman passed, there was a definite hole left in “The Simpsons” that the show could never quite recover from. Aside from playing horrible lawyer Lionel Hutz, Hartman was a wiz at playing the awful has been actor Troy McClure, a man who never met a job he didn’t take. Shameless, egomaniacal, and a ridiculous self-promoter, McClure appeared throughout many episodes of the early seasons of “The Simpsons” in bad TV shows, horrible schlocky movies, infomercials, and even experienced a comeback in the Planet of the Apes musical. His endless resume of bad movies and short films will always be remembered alongside his final appearance as an automated theme park greeter.

Ron Howard as Himself
(When You Dish Upon a Star)
Apparently all big movie stars hang out with one another and crash each other’s houses in towns housing the Simpsons, and Ron Howard, Hollywood director is one of them. Playing a hilarious supporting role in “When You Dish Upon a Star,” Howard spoofs himself as an alcohol fueled and inept fellow who constantly feuds with Homer. Homer of course occasionally identifies him by Potsie. Ron Howard takes a good turn as a satirizing of himself in this episode, and nearly pays for his life during a high speed chase. But at least he sells a new hit movie to his friend Brian Grazer about killer robot driving instructor that travels back in time for some reason.

Kelsey Grammar as Sideshow Bob
(Various Episodes)
Before the show inevitably ruined it, Kelsey Grammar had a pretty sweet gig as Bart Simpsons’ nemesis Sideshow Bob. He attempted to frame Krusty and Bart foiled him, he ran for mayor and Bart foiled him, he tried to kill aunt Selma and Bart foiled him, he tried to blow up Springfield and Bart foiled him, he tried to kill Bart and Bart foiled him, and–you know what? Sideshow Bob just isn’t as brilliant as her perceives himself to be. But Kelsey Grammar’s hysterical portrayal of this wretched villain with egomania is one of the highlights of the series, and Bob has proven to be an excellent villain in Bart’s otherwise villain laced world.

Glenn Close as Mona Simpson
(Mother Simpson)
Glenn Close manages to hold her own against Dan Castellaneta as one of the stalwart Simpsons who broke free from the repressive life of marriage from Abe Simpson to find herself. Unfortunately that search got her in to a lot of trouble and she had to abandon Homer and leave him with a rift in his life. As Mona Simpson, she’s a wonderful and warm hearted character who loves Homer in spite of his simple minded antics and inability to catch on to the even the most fundamental concepts, but due to crossing her biggest nemesis Monty Burns, she has to live life on the lam. She’s an ill-fated freedom fighter of the sixties who lives on in Homer. As we’ll find out later in the series.

Albert Brooks as Hank Scorpio
(You Only Move Twice)
Homer works for one of the most evil men in America, a man consistently destroying the Ozone, the environment, who has blocked out the sun and has frequently planned to dominate the world. So it only makes sense someone like Hank Scorpio would take an interest in what Homer has accomplished in the past. Hank Scorpio is a nice boss who treats his workers well. And wants to dominate the world, in the process. Albert Brooks returns yet again as the hysterically evil Hank Scorpio who takes on James Bond and wins with the help of Homer Simpson, and pays him off with the Denver Broncos. It’s not the Cowboys, but it’s just as good, I guess.

Honorable Mention:
Alan Moore
(Husbands and Knives)
Regardless of what you think of Moore for refusing to submit to the commercialization of his creative works as dignified and subversive or just plain obnoxious, the man’s appearance during the nineteenth season is a tasty bit of self satire that proves the man at least has a sense of humor. Basically spoofing himself he is forced to endure the praise of Bart’s satisfaction of his treatment of Radioactive Man and loses it when Milhouse asks him to sign his DVD of “Watchmen Babies: V for Vacation.” He’s told to calm down by Daniel Clows and we discover the only thing that can calm him is his love for “Little Lulu.” Later it’s revealed he and two other world renowned comic book authors are a team of superheroes. It’s truly a great appearance for anyone familiar with Moore’s controversial attitude toward the treatment of his books.

DIS-Honorable Mention:
Ellen Page
(Alaska Nebraska)
Don’t get me wrong, I am head over heels in love with Ellen Page. Not only is she beautiful, but she’s bright, intelligent, skilled and can make almost any movie remotely watchable, but as is the case with most guest stars on “The Simpsons” these days, Ms. Page was totally and utterly wasted in her guest appearance. The “Alaska Nebraska” episode is a let down on two levels. On the one side, the entire episode is a spoof of Hannah Montana and there’s not much satire to be had in this episode. And it all builds up to finally seeing Alaska as played by Page who only appears for five freaking minutes. On a second level, Page’s appearance isn’t funny. She goes on an endless monologue about stardom and how she’s really just an adult who smokes and drinks coffee, but beyond that she barely says anything worth a chuckle, thus Page is wasted yet again in a famous pop culture series. Sad waste of talent and time, for Ms. Page.