1. Albert Brooks as Jacques (“Life on the Fast Line”)
Albert Brooks has made several appearances on The Simpsons, but his first appearance was as Jacques, for which he adopted a French accent. Jacques was Marge’s bowling instructor, with whom she came very close to having an affair.
2. Penny Marshall as Ms. Botz (“Some Enchanted Evening”)
Penny Marshall took on the role of evil babysitter Ms. Botz. Bart and Lisa discover that the woman watching them is a criminal and tie her up, but Homer — not knowing her true identity — sets her free before police arrive.
3. Dustin Hoffman as Mr. Bergstrom (“Lisa’s Substitute”)
Dustin Hoffman didn’t want to be credited, so he was listed as Sam Etic. (Like “Semitic.” Clever, no?) But more than 20 years since his episode, Mr. Bergstrom remains one of the most beloved one-off Simpsons characters.
4. Michael Jackson as Michael (“Stark Raving Dad”)
Like Dustin Hoffman, Michael Jackson used a pseudonym. (“John Jay Smith,” which is not as fun.) He played Leon Kompowsky, a mental patient who claimed to be Michael Jackson. Michael sounded very authentic — and with good reason.
5. Jacki Mason as Rabbi Krustofski (“Like Father, Like Clown”)
Legendary Jewish comedian Jackie Mason provided the voice for Krusty’s disapproving father, Rabbi Hyman Krustofski. The episode “Like Father, Like Clown” was a parody of The Jazz Singer.
6. Beverly D’Angelo as Lurleen Lumpkin (“Colonel Homer”)
Beverly D’Angelo was Lurleen Lumpkin, the country singer Homer managed. The character showed up later in the series, but her voice had gone to hell, so D’Angelo was replaced by Doris Grau, better known as Lunchlady Doris.
7. Kimmy Robertson as Samantha Stankey (“Bart’s Friend Falls in Love”)
Kimmy Robertson may not have the instant name recognition as other actors on this list, but you know her voice well. And you probably know the face, too: she played Lucy in Twin Peaks and Cathy in Don’t Tell Mom the Babysitter’s Dead.
8. Sara Gilbert as Laura Powers (“New Kid on the Block”)
Back when she was Darlene on Roseanne, Sara Gilbert popped over to The Simpsons to voice Laura Powers, Bart’s new neighbor, babysitter, and crush. She broke his heart when she revealed she was dating Jimbo.
9. Elizabeth Taylor as Maggie Simpson (“Lisa’s First Word”)
Yep, Maggie’s first word was spoken by Elizabeth Taylor. The iconic film star would appear again on the series as herself — it was a much heftier role, though her voice cameo in “Lisa’s First Word” still made TV history.
10. Michelle Pfeiffer as Mindy Simmons (“The Last Temptation of Homer”)
In the early ’90s, Michelle Pfeiffer was serious temptation for most men, and Homer was no different. As Mindy, she nearly lured Homer into the dark world of corporate retreat infidelity.
11. Sam Neill as Molloy (“Homer the Vigilante”)
Sam Neill played the charming cat burglar Molloy, who inspired Homer to start a neighborhood watch group. He eventually escaped by tricking the entire town of Springfield, which isn’t really that difficult.
12. Kathleen Turner as Stacy Lovell (“Lisa vs. Malibu Stacy”)
Kathleen Turner’s inimitable voice was the perfect fit for Stacy Lovell, the bitter alcoholic creator of the Malibu Stacy doll. She and Lisa teamed up to fight the misogyny in dolls marketed to young girls.
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