Havana (1990)

Synopsis
A cynical gambler reluctantly comes to the aid of a mysterious beauty in this interpolation of Casablanca and the real-life Cuban revolution. Big-stakes American gambler Jack Weil (Robert Redford) is comfortable in the anything-goes Havana of 1958. But with Fidel Castro out in the wilderness broadcasting revolutionary messages, it seems the good times may be on the way out. On a boat back to the island nation from the U.S. mainland, Weil agrees to help beautiful Bobby Duran (Lena Olin) smuggle in some contraband by trading vehicles with her on their way through the checkpoint. He's amused to discover not jewelry, but radio transmitters squirreled away in her car. Eventually, he learns that she's the European wife of monied Cuban communist Arturo Duran (Raul Julia), who believes his class and status will protect him from the ruling party. When that assumption turns out to be false, Jack finds himself sucked in by the plight of the suddenly widowed Bobby, who remains committed to her dangerous ideals. Risking his cushy lifestyle to protect Bobby from the coming tumult -- and from herself -- Jack must grapple with the dictates of his newfound conscience. With a supporting cast that includes Alan Arkin and Tomas Milian, Havana reunited director Sydney Pollack with Redford and David Rayfiel, star and co-screenwriter of The Way We Were. Rayfiel has also worked on a number of Pollack pictures, stretching from 1969's Castle Keep to 1995's remake of Sabrina. ~ Brian J. Dillard, All Movie Guide