The flag flown by Morgan Adams was in reality the flag flown by "Calico" Jack Rackham, one of the only Caribbean Pirates to have women on his crew; Anne Bonny and Mary Read. He later turned his ship over to the two women.
Originally scheduled to star Michael Douglas, who pulled out claiming that Geena Davis' role was expanded at his character's expense.
Director Trademark: [Renny Harlin] [[flag]: Shopfront window. See also the goofs entry.]
Geena Davis did most of her own stunts for the film. Renny Harlin is famous for pushing the actual actors to do their own stunts whenever possible. While promoting the film, Geena Davis appeared on talk shows with clips of her doing the stunts over and over (including one take where she fell out the window too soon, rolled down the roof and under the carriage) and explaining the bruises and injuries she sustained while filming.
Dawg Brown's flag is the flag used by Captain Emmanuel Wynne, the oldest known "Jolly Roger" flag.
Dawg's outfit matches that of pirate captain Kit Oloard.
Bankrupted Carolco Pictures, the production company behind the movie.
The "impossible" stunt where Geena Davis appears to jump out of a window, roll on the roof of a building and then land on a moving carriage was actually done by digitally compositing two separate shots: one of her falling, and another of her already in the carriage, pretending she's just landed there.
Oliver Wood was the film's original director of photography. An accident on the set caused him to break his ankle, and he and was immediately replaced by Peter Levy. The injury also cost Wood his next job on Broken Arrow (1996); he was replaced by Levy on that film as well.
Oliver Reed was originally cast as Mordechai Fingers but was fired from the production after becoming involved in a bar fight and mooning at Geena Davis. He was replaced by George Murcell.
Renny Harlin was dating Geena Davis at the time and convinced Mario Kassar that Davis should take the leading role. Davis at the time was only known for light comedies, and Harlin was sure this would turn her into an action-adventure star.
Mario Kassar decided to get the movie started by building sets, ships, and other logistical details started in Malta even before the first revised draft of the script was ready. He also managed to sell the foreign distribution rights before the first revised draft.
According "Guinness Book of Records", this picture is the biggest financial loss to this date.
Michael Douglas originally agreed to do the film on two conditions. First, the filming had to start immediately because he was only available for a limited time. Second, his character had to have the same amount of screen time as Geena Davis.
One of the photography directors broke his leg falling off a crane.
Broken pipes caused raw sewage to pour into the water tank where the actors were supposed to swim.
When director Renny Harlin fired the chief camera operator following a dispute, more than two dozen crew members showed their solidarity by quitting too.
Total cost: $115 million. Total box office earnings: $10 million. Total loss: $105 million.
Director Renny Harlin made the film specifically to launch his wife, Geena Davis, from comedies into action films.
Renny Harlin was so preoccupied with trying to find a male lead after Michael Douglas quit that the set construction and script work was done without his input. When shooting was set to begin, he didn't like what he saw, so massive rebuilding and rewriting had to be done, at increased expense.
After Michael Douglas quit, Geena Davis wanted to leave too. However, she was contractually obligated to finish the film.
Carolco Pictures, which had financed Cutthroat Island, filed for bankruptcy six weeks before the film actually reached the theaters.