Actor Raul Julia appeared in a significant supporting role in the film without any credit or billing at all in the film. Julia chose to be uncredited because producers for contractual reasons could not accommodate Julia's request for him to be billed second alongside Robert Redford, as the top two above-the-title star-teaming credits had already been signed over to top first-billed Redford and second-billed actress Lena Olin, with the third billed credit already having been contracted to actor Alan Arkin. According to the "LA Times", Raul Julia's agent Jeff Hunter said: "Our usual above-the-title credit wasn't available. So we decided not to take any credit at all". Director Sydney Pollack said told the same paper: "The only billing left for Julia was to be stacked with the rest of the names . . . his agent felt that would be a step backward" and there is a dilemma when there is "an actor on the ascendancy, like [Raul] Julia, and you ask the actor to do a role that's somewhat smaller [than their emerging star status]". Julia had found rising star status since his performance in the Academy Award winning film Kiss of the Spider Woman (1985).
Director Sydney Pollack originally wanted to film the picture in Havana itself. Reportedly, the reasons for why this could not be achieved were threefold: (1) American citizens could not legally go to Cuba at the time (2) United States of America law prohibited producers spending money in Cuba at the time and (3) International relations between Cuba and the USA at the time in 1989-1990 were politically sensitive and were inimical to shooting in Cuba. Alternately, therefore the film was shot somewhere else, and filmed entirely in the Dominican Republic in the Caribbean region of Central America.
Many of the extras and background artists in the picture were exiled and political refugee Cubans who had migrated from Cuba to the Dominican Republic where the movie was shot. Director Sydney Pollack has said of this: "The atmosphere became quite emotional . . . They remembered the old days in Havana. Our set took them back thirty years".
Final cinema movie collaboration of director Sydney Pollack and star Robert Redford. The picture was made and released about five years after their penultimate venture Out of Africa (1985) which had won seven Academy Awards including Best Picture.
The picture featured about 2000 extras and background artists requiring around 8000 to 10000 outfits and costumes with many of these requiring many and frequent costume changes throughout the film's production.
The film's main set, called "The Big Set", was a quarter-mile long street surrounded by facades representing casinos, restaurants and hotels. Interior scenes were shot in replicated casino floors, room suites and cafes. The Prado was replicated by the producers at a former air base in the Dominican Republic. To replicate the Prado, a team of about 300 tradesmen was used over 80 neon signs which needed to be made in the U.S. and shipped to the Dominican Republic. It took 20 weeks to construct "The Big Set".
Lena Olin was dating Robert Redford. They started dating in 1990 after meeting on the sets of the movie "Havana" The kiss" at the Première of the movie was for real. They say that after the Movie was finished Lena & Redford had a love affair till 1991.
It was decided to make the entire film in the Dominican Republic. The vegetation was the same, and Santo Domingo offered certain architectural similarities, though not a wide boulevard like Havana's famous Prado (Paseo de Marti). The end scene was filmed in Key West, Florida.
Nick Nolte was originally considered for the lead role but it ended up going to Robert Redford. Redford and Nolte worked in 2 films together many years later: "The Company You Keep" (2012) and "A Walk In the Woods" (2015).