Q: For which movie did Bob Dylan win his only Academy Award® for Best Original Song? Here’s a hint: The 2000 comedy was adapted from a Michael Chabon novel of the same name.
A: Wonder Boys
Dylan's Oscar® was the only one received by the film, which had a star-studded cast including Michael Douglas, Tobey Maguire, Frances McDormand, Robert Downey Jr., and Katie Holmes. Douglas’s character, a professor famously suffering from writer's block after publishing his first novel to great acclaim, was inspired by author Michael Chabon's real-life professor at the University of Pittsburgh, Chuck Kinder.