A box office disaster is often far more interesting than a box office success story. These days, things only fail to meet expectations because those expectations are completely unreasonable. There was a time before franchise media ruled the world when a single film could flop hard enough to fundamentally change the cinematic landscape. In 1995, Cutthroat Island gave the world a perfect example.
Imagine a new action film got announced tomorrow. It's like a lot of other action films, but it's primarily a knock-off of John Wick. The world has already seen dozens of films best described as "Wick, but with another actor in the suit," but this one is different. This one is a box office failure of epic proportions. Imagine the world then went a decade without another John Wick action movie. That's what Cutthroat Island did for the venerable world of pirate movies.
Cutthroat Island is a swashbuckler in the style of dozens of classic adventure films. It was proposed in the early 90s with a noble goal; give Geena Davis the role that will make her an action star. Davis was known at the time for comedy films like Beetlejuice and A League of Their Own, but she had designs on the glamorous life of an action hero. Davis was married to Renny Harlin, the director of Cutthroat Island. Harlin convinced producer Mario Kassar to give Davis the part while also guaranteeing its success. Carolco Pictures, Kassar's production company, wagered absolutely everything they had on the project. Unfortunately, it was perhaps the worst bet in film history.
Carolco was drowning in debt when Harlin pitched Cutthroat Island, so they were in desperate need of a savior. They were convinced that Harlin's pirate film would do what they needed, so they canceled everything else they had a stake in. They pulled funding from a film called Crusade that would've starred Arnold Schwarzenegger at the height of his celebrity. They sold their interest in Showgirls, Last of the Dogmen, and Stargate. Dogmen was a disaster, but Showgirls made tons of money on home video sales and Stargate was a runaway hit. They had more faith in Cutthroat Island than anyone should reasonably have in anything.
Casting the film was a nightmare. Michael Douglas was originally cast opposite Davis in the lead role, but he left the project because he felt that his character was being sidelined to make more room for Davis. A conga line of big-name movie stars turned down the leading role after Douglas quit. Tom Cruise, Keanu Reeves, Liam Neeson, Charlie Sheen, Jeff Bridges, Russell Crowe, Michael Keaton, and Daniel Day-Lewis, all got the call and all resolutely refused. After so many rejections, they found their star in Matthew Modine. He's probably best known now for his role as Dr. Brenner in Stranger Things but he took the Cutthroat Island role because he had a background in fencing.
The production continued to be disastrous after their lead was cast. Harlin was reportedly a nightmare on set. After a particularly nasty altercation, more than 25 crew members bailed at once. Since they were bleeding money, Carolco couldn't afford to fill all the positions, and mistakes were made. An area that was set aside for actors to swim became bombarded with raw sewage. Cinematographer Oliver Wood, who went on to work on Face/Off and the Bourne movies, fell off a crane and broke his leg, forcing him to leave the project. Harlin wanted actors to do their own stunts whenever possible. Even his wife was injured repeatedly on set. It was a bad shoot, but at least the finished product was despised by critics and ignored by audiences.
Cutthroat Island made $10 million off of its nearly $100 million budget. It's a nightmarish loss before even considering how much potential profit could've been made from their other projects. Obviously, it was the death blow that ended the company. It was also a pretty substantial blow to Geena Davis, who went on to star in similarly massive flop The Long Kiss Goodnight the following year, which was also directed by Harlin. Harlin, for his part, has his name on classics like Deep Blue Sea, 12 Rounds, and the 2014 Legend of Hercules movie. Davis incidentally filed for divorce in 1998, after her personal assistant gave birth to Harlin's first son.
Among Cutthroat Island's many victims, the entire genre of pirate movies suffered a massive blow. Hollywood looked at the disastrous production, stupid self-centered concept, and nightmarish execution and decided that the problem was the film's genre. Studios were unwilling to give pirate movies a chance until Pirates of the Caribbean came along and made millions. Even now, swashbucklers can't make it through the door without the right brand name attached. Some even contend that it stood as an argument against big films led by women, making its failure somehow sexist on top of everything.
Cutthroat Island was a miserable experience on all fronts. It should stand today as a lesson to everyone with any involvement in the world of cinema. The story of Cutthroat Island is a sad one for all involved, but at least it's pretty funny to watch rich people make bad bets and lose.