| Role (on the Simpsons) | Actor | Oscar Winning Film(s) |
|---|
| Mr. Bergstrom, the title character in the episode 'Lisa's Substitute' | |
| Mrs. Glick, the old woman who gives Bart a quarter for weeding her monstrous garden in 'Three Men and a Comic Book' | |
| Maggie in 'Lisa's First Word,' and herself, refusing to appear on Krusty's comeback special, in 'Krusty Gets Kancelled' | |
| Himself, as the 'special celebrity dad' brought in to replace a boy's dead father on a father-son rafting trip, in 'Boy-Scoutz in the Hood.' | |
| The nameless, (presumably Russian) ballet teacher in 'Homer Vs. Patty and Selma,' and herself, in 'Bart Has Two Mommies' | |
| Jessica Lovejoy, the seemingly innocent reverend's daughter who turns out to be a sociopath in 'Bart's Girlfriend' | |
| Dr. Zweig, Marge's therapist (also known as 'Lowenstein') in 'Fear of Flying' | |
| Frank Ormand, the franchise salesman who convinces Marge to buy one of his pretzel carts, in 'The Twisted World of Marge Simpson' | |
| | Role (on the Simpsons) | Actor | Oscar Winning Film(s) |
|---|
| Renee, the woman who inexplicably is willing to date Moe (who attempts insurance fraud so he can romance her in style), in 'Dumbbell Indemnity' | |
| Herself, who (alongside her then-real-life-husband) hires Homer as a personal assistant, in 'When You Dish Upon a Star' | |
| Jim Hope, the 'teacher' who really works for the company that creates the Funzo toy in 'Grift of the Maji' | |
| Greta Wolfcastle, the daughter of Rainier, who dates Bart and then falls for Milhouse in 'The Bart Wants What It Wants.' | |
| Sara Sloane, a famous actress who has a whirlwind romance with Ned Flanders in 'A Star is Born Again' | |
| Melanie Upfoot, the politically correct principal who teaches the girls when Springfield Elementary is divided by gender in 'Girls Just Want To Have Sums' | |
| Maggie (different actress this time), in the season 20 episode, 'Four Great Women and a Manicure' | |
|
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