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According to Collider, season 34 of The Simpsons will include such guest stars as Simu Liu and Melissa McCarthy. From Leonard Nimoy to Elton John to Stephen Hawking to Mick Jagger to Mark Hamill to Lady Gaga to all the Major League ringers Mr. Burns hires for his softball team in “Homer at the Bat,” many famous faces have appeared as themselves in The Simpsons. But some of the show’s most memorable celebrity guest performances have been as one-off characters.
From Kelsey Grammer as Sideshow Bob to Glenn Close as Mona Simpson to Albert Brooks as Hank Scorpio (among others), some of the best Simpsons guest stars have played fictional characters.
10/10 Willem Dafoe As The Commandant
When Bart is sent to military school as punishment for a monumental prank, his sister decides to join him for a challenging education in the season 8 finale “The Secret War of Lisa Simpson.” Willem Dafoe gives a hilariously deadpan guest performance as the Commandant of this military school.
From his “lights out” toe-stubbing to his speech about future wars fought by robots in space, Dafoe has many memorable moments in this role.
9/10 Michelle Pfeiffer As Mindy Simmons
In the season 7 episode “The Last Temptation of Homer,” Homer is tempted to have an affair when he gets to know his ridiculously attractive new co-worker Mindy Simmons and learns that she’s exactly like him. She loves beer, watches a ton of TV, and drools over donuts.
A-list guest star Michelle Pfeiffer gives an unforgettable vocal performance in the role. She brings a satirical self-awareness to Mindy’s overtly seductive flirtations.
8/10 Mandy Patinkin As Hugh Parkfield
Lisa got a glimpse at her future in the fan-favorite flash-forward episode “Lisa’s Wedding.” As foreseen by a fortune teller, Lisa will grow up, attend a fancy college, and fall in love with a charming English classmate named Hugh Parkfield.
Mandy Patinkin portrayed Lisa’s fiancé as a spot-on parody of the awkward, stuttering, dry-humored romcom protagonists played by Hugh Grant.
7/10 Danny DeVito As Herb Powell
The season 2 episode “Oh Brother, Where Art Thou?” introduced Homer’s long-lost half-brother Herbert Powell, a self-made millionaire who earned his fortune as a car manufacturer. Unsurprisingly, that fortune doesn’t last long after he meets Homer and hires him to design a new car. In the role of Herb, Danny DeVito is as hilarious as always as a foil for Homer.
DeVito’s performance as Herb proved to be so popular that fans wanted him to have a happier ending, so the writers came up with “Brother, Can You Spare Two Dimes?” in season 3, in which he earns back his millions.
6/10 Patrick Stewart As Number One
Homer joins a secret society called the Stonecutters in season 6’s “Homer the Great.” He’s initially kicked out of the Stonecutters for accidentally destroying their sacred scroll, but takes over as their leader when they discover a birthmark that resembles their logo. Patrick Stewart guest-stars as the head of the Springfield chapter of the Stonecutters, “Number One.”
Stewart was perfectly cast in this role, as his voice and acting style have the theatrical gravitas to sell grandiose lines like “shatter the stone of ignorance to bring forth the light of truth,” and also to undercut that grandiosity with absurdist one-liners like “the paddling of the swollen a**.”
5/10 Meryl Streep As Jessica Lovejoy
In the season 6 episode “Bart’s Girlfriend,” Meryl Streep played Bart’s titular love interest, Jessica Lovejoy. Jessica is introduced as a sweet, harmless reverend’s daughter, but she turns out to be even more dastardly than Bart.
Trust a world-class thespian like Streep to capture this dichotomy perfectly. The innocence of Jessica’s voice contrasts hysterically with her amoral actions to fit in with the storyline of Bart struggling to break her spell over him.
4/10 Kelsey Grammer As Sideshow Bob
Kelsey Grammer’s most iconic TV role will always be Dr. Frasier Crane, but The Simpsons’ Sideshow Bob is a very close second. Although he was introduced as Krusty the Clown’s resentful former sidekick, Bob has become much more notorious for his murderous vendetta against Bart.
Grammer always leans into Bob’s villainy, but never at the expense of the comedy. From his deadpan reactions (“Rakes, my old arch enemy…”) to his surprising whimsy (singing the H.M.S. Pinafore lyrics before killing Bart), Grammer’s performances as Bob are always hysterical.
3/10 Dustin Hoffman As Mr. Bergstrom
Dustin Hoffman guest-starred in the season 2 episode “Lisa’s Substitute” as Mr. Bergstrom, the sub who takes over Miss Hoover’s class while she’s on medical leave with what she believes is Lyme disease. Lisa is inspired by Mr. Bergstrom’s engaging teaching style and passion for imparting knowledge.
Hoffman’s warm, affable portrayal of Mr. Bergstrom offers a stark contrast to Homer’s boorishness as Lisa becomes infatuated with this new father figure.
2/10 Glenn Close As Mona Simpson
The season 7 episode “Mother Simpson” finally introduced Simpsons fans to Homer’s mom, who abandoned him as a child to join the counterculture rebellion of the 1960s. Glenn Close nailed both the comedic line deliveries and the dramatic nuance of Mona’s long-awaited return.
Mona’s farewell at the end of the episode always chokes up fans, thanks to Close’s heartfelt delivery: “Remember, whatever happens, you have a mother, and she’s truly proud of you.”
1/10 Albert Brooks As Various Characters
Always credited as “A. Brooks,” Albert Brooks has guest-starred in a bunch of Simpsons episodes – and the movie, playing the villainous Russ Cargill – and his characters are all wildly different from one another.
From seductive French bowler Jacques to soft-voiced self-help guru Brad Goodman to upbeat James Bondian supervillain Hank Scorpio, Brooks’ one-off Simpsons characters always stand out.
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