6. Masked and Anonymous (2003)
The Ensemble: Bob Dylan, Jeff Bridges, John Goodman, Giovanni Ribisi, Penelope Cruz, Val Kilmer, Mickey Rourke, Jessica Lange, Luke Wilson, Bruce Dern, Cheech Marin, Ed Harris, Sean Penn, Angela Bassett When director Larry Charles set out to create a movie "like a Bob Dylan song," you wouldn't have thought him to meant one of the bad songs. You might not have expected him to have cast Bob Dylan himself in a starring role, either, but that totally happened, too.
Masked and Anonymous made less than a million dollars as the box office, despite the fact that it stars Jeff Bridges and John Goodman. It's Dylan who's the big problem, though. As you might have gathered, despite being one of the greatest (if not the greatest) singer/songwriters of all time, the man cannot ask to save his live. He grumbles his way through this ensemble drama about a former rock legend who gets bailed out of prison so he can perform a one-man benefit concert in twisted North American future (?). The film was panned as a vanity project, and the cast are squandered on Dylan's own screenplay.