Matthew Modine several years later went on record to explain some of the reasons why the film's costs spiraled so much and became such an expensive flop. He cited one example where cases and cases of V8 juice were shipped out to Malta, expressly for director Renny Harlin and his wife Geena Davis. Towards the end of the shoot, the juice was served up for everybody as there was an entire room of it to be dispensed with. He also said that every scene had three cameras in constant use, resulting in tons and tons of film being used for every shot.
Michael Douglas originally agreed to do the film on two conditions: filming had to start immediately because he was only available for a limited time, and his character had to have the same amount of screen time as Geena Davis. Douglas eventually pulled out, claiming that Davis's role was expanded at his character's expense. Davis wanted to quit when Douglas did, but she was contractually obligated to finish the film. After Douglas quit, Renny Harlin was so preoccupied with trying to find a male lead that set construction and script work were done without his input. Harlin didn't like what he saw when shooting was set to begin, leading to massive, expensive rebuilding and rewriting.
Before this film went into production, Geena Davis and Michelle Pfeiffer were in talks to star in a pirate movie called Mistress of the Seas. Paul Verhoeven was in talks to direct. Ironically, that movie was shelved because the studio could not persuade Verhoeven to cast Harrison Ford in the lead, as they didn't believe an action film with a female lead could be financially successful.
Renny Harlin is famous for pushing actors to do their own stunts whenever possible. While promoting the film, Geena Davis appeared on talk shows with clips of her doing stunts over and over (including one take where she fell out of the window too soon, rolled down the roof and under the carriage) and explained the bruises and injuries she sustained while filming.
Oliver Wood was the film's original director of photography. When he broke his ankle in an accident on set, Peter Levy immediately replaced him. The injury cost Wood his next job on Broken Arrow (1996); Levy replaced him there, too.
At the time, Renny Harlin was dating Geena Davis, who was known for light comedies. He convinced Mario Kassar to cast Davis as the lead, sure it would turn her into an action-adventure star. The couple married prior to production, and affectionately called the movie their 'honeymoon'.
Matthew Modine described Oliver Reed - "I'd heard these stories about Oliver Reed I think it is all bunk. Oliver was a gentleman. Sure, he had a reputation as a man who enjoyed a drink. But only off set. His reputation as an actor is stellar. Professional. I stand by that. God rest his soul."
Geena Davis' "impossible stunt" (jumping out of a window, rolling onto the roof of a building, and landing on a moving carriage) was a digital composite of two shots; one shot of her falling, and a second shot of her already in the carriage, pretending she just landed there.
Carolco Pictures had finished preproduction on another mega production at the time, called 'Crusade', to be directed by Paul Verhoeven and starring Arnold Schwarzenegger. Filming was slated to begin, but the movie was canceled at the last moment, when Carolco could not finance two blockbusters at the same time. They opted to do this film, which was supposed to have been less costly, but which later went massively over budget, and put the already ailing studio further in debt. Verhoeven went on to make Showgirls (1995) instead, largely as a favor to Mario Kassar in an attempt to save Carolco from financial downfall. After both Cutthroat Island and Showgirls bombed at the box office, the studio was bankrupted, and Crusade was shelved indefinitely.
In a radio interview in 2011, Renny Harlin discussed the film's box office failure. He pointed out that Carolco was already in ruin before the film even began shooting, but had to make the film since financing from foreign investors was already in place. MGM, the film's distributor, was in the process of being sold and thus could not devote itself into financing a marketing campaign for the film.
Mario Kassar decided to start production by building sets, ships, and other logistical details in Malta before the first revised draft of the script was ready. He also sold the foreign distribution rights before the first revised draft.
Frank Langella considers Dawg to be one of his three favourite roles (the other two are Richard Nixon in Frost/Nixon (2008) and Skeletor in Masters of the Universe (1987)), because he got to not only be a pirate, but a scenery-chewing over-the-top bad guy pirate. Apparently, the man loves being able to just go for broke in a role.
Due to the casting distractions, Renny Harlin hadn't really been able to pay attention to the sets and production design. When he finally did, he didn't like any of it. It all had to be redesigned and rebuilt in a rather short time frame-and then the script had to be rewritten to accommodate the changes. Both had a lot to do with driving the film's budget way up.
The origins of this movie actually date back to 1986 when a movie called Bloody Bess was in production. The movie also starred a female swashbuckler, but was set to be a lot more violent and darker than Cutthroat was. The movie was cancelled but Renny Harlin, who was working at Empire Studios at the time the film was in talks, liked the idea of a female pirate and reused it later on.