With The Simpsons deep into its twentieth season, the list of celebrities who’ve done cameos on the show is extensive and impressive. At this point, being invited to voice a character is akin to hosting an episode of Saturday Night Live. It’s become a rite of passage in Hollywood, what celebs do to prove that they’ve made it. Just like SNL guest stars, there are some who call it in and others who make their characters legendary. And they’re especially great when they keep the Simpson clan—and the audience—on their toes.
1. Hank Scorpio (Albert Brooks)
Best. Super-villain. Ever. Brooks’ slightly raspy voice and upbeat delivery of Hank’s lines made him endearing, even after he blew up a bridge, threatened to blow up France, and seized the East Coast.
Best line: We don’t have bums in our town, Marge, and if we did they wouldn’t rush. They’d be allowed to go at their own pace.”
2. Lyle Lanley (Phil Hartman)
Hartman often lent his voice to The Simpsons in the form of Troy McClure and Lionel Hutz, but one of his standout episodes was when he appeared as a crooked monorail salesman who tricked Springfield into investing in his fraudulent business.
Best line: “I’ve sold monorails to Brockway, Ogdenville, and North Haverbrooke, and by gum, it put them on the map!”
3. Sideshow Bob Terwilliger (Kelsey Grammar)
This TV bad guy has yet to actually succeed at killing anyone, but that’s not for a lack of trying. His charming, baritone voice and refined tastes make him seem an unlikely villain, but as soon as Grammar introduces his famous maniacal laugh, there’s no doubt about his character’s insanity.
Best line: “Lisa, you don’t spend ten years as a homicidal maniac without learning a few things about dynamite.”
4. Jessica Lovejoy (Meryl Streep)
She’s the only character who surpasses Bart in terms of troublemaking, which only makes him like her more. Streep’s sugary voice made Jessica’s razor-sharp dialogue seem sweet and creepy all at once.
Best line: “I’m the minister’s perfect daughter and you’re just yellow trash.”
5. Artie Ziff (Jon Lovitz)
He almost managed to take Marge away from Homer back in high school and again by spending a weekend with her, but Lovitz’s smarmy Artie can’t compete with Homie.
Best line: “Marge, I would appreciate it if you didn’t tell anyone about my ‘busy hands.’ Not so much for myself, but I am so respected, it would damage the town to hear it.”
6. Fat Tony (Joe Mantegna)
Yet another character who regularly pops up to wreak havoc on the town by using shoddy equipment to work on the elementary school, trying to kill the mayor, and using Bart as a bartender. But Mantegna’s husky voice makes everything sound so deliciously sinister, we keep hoping he’ll keep stirring up more trouble.
Best line: “I don’t get mad … I get stabby.”
7. Cecil Terwilliger (David Hyde Pierce)
In a clever bit of casting, Pierce was brought on to play brother to Grammar’s Sideshow Bob at the same time they played siblings on Frasier. Cecil was even more demented than Bob—he turned on his own brother because he wanted to be Krusty’s sidekick—but just as unsuccessful and villainy.
Best line: “And now to kill you. There may be a slight ringing in your ears. Fortunately, you’ll be nowhere near them.”
8. Mindy Simmons (Michelle Pfeiffer)
She’s the female version of Homer when it comes to gluttony, which makes Homer confused about his feelings for her. She almost lures him away from Marge at a National Energy Convention in Capital City, but Homer remains faithful and, according to him, she “hits the bottle pretty hard” afterward.
Best line: “Let’s do it … let’s order room service!”
9. Molloy the Cat Burglar (Sam Neill)
Neill has said that providing the voice of Molloy was a career high-point, and after watching him swindle Springfield residents out of their prized possessions (Lisa’s saxophone, Bart’s stamp collection, etc.), it’s clear he makes an enthralling criminal.
