A lavish Hollywood production that recreated 1950s Cuba, only to fail at the box office.

Entertainment · Published 3 October 2026 Swipe more like this →

In short: Sydney Pollack’s 1990 drama Havana was a massive undertaking, featuring a quarter-mile-long set and thousands of period costumes. Despite its meticulous attention to detail and an acclaimed musical score, the film struggled to connect with audiences, resulting in the first major financial deficit of Robert Redford’s storied career.

Set against the backdrop of the Cuban Revolution’s final days in 1958, the film follows Jack Weil, a professional gambler played by Robert Redford, who becomes entangled with a revolutionary leader’s wife. The production faced significant logistical hurdles; due to U.S. law, the crew could not film in Cuba, forcing them to recreate the city in the Dominican Republic. A team of 300 tradesmen spent 20 weeks constructing a massive set, complete with 80 imported neon signs and over 100 vintage vehicles to capture the era's atmosphere.

The film’s commitment to historical accuracy was noted by cast members like Tomás Milián, who lived in Cuba during the 1950s and praised the recreation. Many extras were exiled Cubans, making the experience deeply emotional for those who remembered the period. Despite these efforts, critics were largely unimpressed, describing the film as dramatically inert. It holds a 28% rating on Rotten Tomatoes, and audiences polled by CinemaScore awarded it a C+ grade.

Financially, the project was a disappointment. With a budget of $40 million, it grossed only $9 million domestically and $27 million internationally, failing to recoup its costs. While the film struggled to find its footing, Dave Grusin’s musical score stood out, earning nominations for an Oscar, a Golden Globe, and a Grammy. Ultimately, the film remains a curious case of high-budget ambition overshadowed by a narrative that failed to resonate with viewers.

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