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.
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