(And, quickly, with apologies to the late-grate Phil Hartman, he was too close to a regular cast member to be considered a guest start in our book. The same goes for Marcia Wallace, Russi Taylor, and Doris Grau, great as they all are.)
5 Michelle Pfeiffer as Mindy in “The Last Temptation of Homer,” 1993
As Mindy, Pfeiffer’s feminine twist on Homer Simpson’s persona is genius. In seriousness, what man in America wouldn’t be attracted to woman that loved donuts and football equally? The entire episode manages to portray the conflict between Homer and Mindy without making either of them look like jerks. Also, the dynamic between them creates some great misdirection in their dialogue: When Mindy says she has a very naughty idea of something they should do, Homer says they should resist their urges, to which Mindy replies, “Let’s do it… Let’s order room service!” Freudian slips and other such innuendos abound in this classic.
4 Jon Lovitz as Llewellyn Sinclair and Ms. Sinclair in “A Streetcar Named Marge,” 1992
Lovitz is another favorite of the Simpsons writers, even managing to voice the tertiary character Artie Ziff who crops up from time to time. But his best performance is in this Marge-centered episode. Lovits pulls double duty as the demented theatrical director Llewellyn Sinclair and his Ayn Rand obsessed sister. Both voices are hilarious and unmistakably Lovitz. As Llewellyn, he gets the chance to reprise his Master Thespian role from Saturday Night Live: “Did I expect to much from fourth graders? I think the review, ‘Play Enjoyed By All,’ speaks for itself!” Ms. Sinclair also presaged what Robin Williams would do with Mrs. Doubtfire a year later.
3 Albert Brooks (A. Brooks) as Hank Scorpio in “You Only Move Twice,” 1996
Albert Brooks is such a regular on Simpsons episodes that he played the malevolent antagonist Russ Cargill in the Simpsons Movie. Besides the movie, he’s had five different guest appearances on the show, playing a different character each time — but being a villain suits him best. So we felt that the Bond-esque villain bent on world domination, Hank Scorpio, was an obvious choice for Brooks’ best roll. What’s funniest about Scorpio is other than blowing up London Bridge and wielding a flame-thrower, he seems like a stand-up guy. OK, maybe a bit wacky… “Have you ever seen a man say goodbye to a shoe?”
2 Rodney Dangerfield as Larry Burns in “Burns, Baby, Burns,” 1997
“Hey, if it gets any livelier in here, a funeral’s gonna’ break out.” Dangerfield obviously wasn’t referring to his own uproarious performance. Recognizing Monty Burns as his long lost father, Dangerfield (a.k.a. Larry Burns) hitches a ride to Burns’ mansion — “I’ve never seen a place with a walk-in mailbox!” Larry soon begins indulging his loafing and drinking addictions on Burns’ dime, taking Homer along for the wild ride. The whole thing results in a hoax kidnapping to win a father’s love followed by a Journey dance party. Dangerfield sparkles throughout, bringing his trademark self-deprecating one-liners into the Simpsons universe with hilarious results.
1 Kelsey Grammer as Sideshow Bob in “Cape Feare,” 1993
The greatest guest star on the Simpsons has become such an institution that his episodes don’t even feel like guest spots anymore — they’ve been woven into the comic tapestry of the Simpsons. Though his first appearance was in 1990’s “Krusty Gets Busted,” we prefer his third appearance most. This is the first time his rivalry with Bart takes the fore, introducing what would become his greatest motivation in the series. (Lest we forget, it also introduced his rivalry with rakes.) Bob is foiled by his love for Gilbert and Sullivan, though it offers the most stunning examples of Grammer’s vocal talents. For the conniving convict in all of us, go re-watch this episode.
Aggggahhhh, Simpsons guest stars, if we could all stop drooling for a second, we’d be able to enjoy just how great these voice-overs are. Since the Simpsons can get everyone they want to do guest voices, this truly represents the cream of the cream of the crop. But we know you comic book guys and die-hard fans are aching to call this the worst list ever! Well, write about it below. Even though you’re already wrong. And, just so you don’t mess yourselves (DMY) all at the same time, here are some other great guest stars that came dangerously close to cracking the top five.
Meryl Streep as Jessica Lovejoy — Who knew Streep had this manipulative little angel hidden inside of her?
Mark Hamill as Himself and Leavelle — Hamill is the only person on this list for playing himself. Good thing he doesn’t take himself too seriously.
Anne Hathaway as Princess Penelope — Hathaway shows some range, copping Jersey accents one minute, then Cinderella singing pipes the next.
Dustin Hoffman as Mr. Bergstrom — Hoffman’s naturalistic performance set a new standard for Jewish cowboys.