Fidel Castro, who died Friday November 25 at age 90, had just come to power when Hollywood stars arrived in Cuba to film Our Man in Havana.

“Cuba – one of the world’s headline danger spots” – this is how the voice in the movie trailer described the country in which Alec Guinness and Maureen O’Hara filmed Our Man in Havana in 1959. The timing could indeed not have been more historically charged: Graham Greene, author of the comedy spy novel upon whch the movie was based, and director Carol Reed, who had previously adapted Greene’s The Third Man, went to Cuba to scout  locations in late 1958. By January 1959 the Batista regime had fallen and the revolutionaries around Fidel Castro and Che Guevara had made it to Havana. Castro was sworn in as Prime Minister of Cuba on February 16, 1959. 

When the crew started filming in April 1959, things had changed quite a bit. Reed told The Daily Telegraph later that “39 changes had been made in the script at the insistence of the Cuban government” to make sure Cuba was shown in a favorable light. The Cuban Minister of the Interior is said to have visited the set unexpectedly. After eventually ironing out all the issues, even el Comandante Fidel Castro himself made an appearance on the set and posed with the Hollywood stars. 

The Cold War comedy revolves around a vacuum cleaner salesman/ British spy who reports fake intelligence back home, which naturally gets him into trouble. It earned a Golden Globe nomination for Best Motion Picture Comedy or Musical in 1961. This year’s drama Papa: Hemingway in Cuba is the first Hollywood production that was shot on the island since Our Man in Havana.