The actress, producer and TV personality gamely took part in a pre-taped video in which Kimmel pitches her increasingly bad ideas for new shows for her Oprah Winfrey Network, including "The Jimmy and Oprah Interview," in which he and Winfrey could ask celebrities such as Jennifer Aniston questions at the same time and see how she reacts.
In another proposed program, "Oprah Repos Her Favorite Things," Winfrey, dressed in sweats and sunglasses, breaks the window of a car and drives off in it, yelling, "I've got a car!"
Winfrey was known for giving away lavish gifts, even cars, to the studio audience of "The Oprah Winfrey Show," which wrapped its 25-year run last May.
Suggesting how he got Winfrey to participate, Kimmel is shown in other footage standing outside her bedroom window with a boom box over his head, just like John Cusack's persistent character does when he tries to win back his ex-girlfriend, played by Ione Skye, in the 1989 teen romance "Say Anything."
Kimmel's special aired on ABC after the 84th Academy Awards telecast.
The program also featured a faux film trailer for "Movie: The Movie," a preposterous Hollywood offering with cameos by George Clooney, Matt Damon, Helen Mirren, Meryl Streep, Gabourey Sidibe, Gary Oldman, Samuel L. Jackson, Bryan Cranston, Emily Blunt, John Krasinski, Kate Beckinsale, J.J. Abrams, Martin Scorsese, John Goodman and Chewbacca.