11/10/2025
Havana (1990)
Directed by Sydney Pollack, Havana (1990) is a romantic drama set against the turbulent backdrop of Cuba in the final days before the 1959 revolution. The film follows Jack Weil (Robert Redford), an experienced but disillusioned American gambler who arrives in Havana looking to profit from high-stakes poker games. Initially detached from politics and uninterested in the brewing unrest, Jack focuses solely on making money and enjoying the city’s glamorous nightlife.
His life changes when he meets Bobby Duran (Lena Olin), the sophisticated wife of a revolutionary leader. Bobby is deeply committed to the Cuban cause, secretly aiding the rebels who are fighting to overthrow Batista’s corrupt regime. Jack is instantly drawn to her beauty and enigmatic strength, despite her emotional distance and dangerous ties. When her husband is arrested and tortured, Jack becomes entangled in a world he had tried to avoid, risking both his safety and livelihood.
As his relationship with Bobby deepens, Jack undergoes a moral transformation. The gambler who once sought only self-interest begins to understand sacrifice, loyalty, and love. He is pulled into the revolutionary struggle, not by ideology, but by his devotion to Bobby. Ultimately, Jack helps her escape, but their love is doomed—Havana falls into the hands of Castro’s revolutionaries, and the world they shared disappears forever.
The film captures the tension of a nation on the brink of change, while weaving a bittersweet romance at its center. With lush cinematography and a nostalgic, melancholic score, Havana reflects themes of love, loss, and political awakening. Often compared to Casablanca for its mix of politics and romance, Havana tells the story of a man who discovers humanity and meaning in the most unlikely place—through a fleeting, passionate love that changes him forever.
