6. 'The Fisher King' (1991)
Terry Gilliam's film fantasy casts Bridges way against type as Jack Lucas, an arrogant prick of a radio shock jock who is ready to off himself when a caller he ridicules opens fire on the patrons of a New York nightclub. Playing against Robin Williams as the instrument of Jack's redemption, the usually sympathetic Bridges plumbs depth of despair in a character who's impossible to like. The risk-taking becomes him.