Awesome, Dear Boy: Frank Langella considers Dawg to be one of his three favorite roles (the other two are Richard Nixon and Skeletor), 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.
Box Office Bomb: Third largest confirmed loss in history at $89 million, $140 million when adjusted for inflation.
Breakthrough Hit: Despite the film flopping, it got John Debney (who mostly had been a television composer before this) noticed in the film scoring circles and launched his career.
Contractual Obligation Project: The film's existence had a lot to do with it being this for many of the people involved. The producers, for example were obligated to make the film because the money had already been raised and Geena Davis and Renny Harlin were contractually tied to do it.
Creator Killer: Cutthroat Island bankrupted the studio Carolco, as well as destroying Geena Davis' career and her then-husband Renny Harlin's respectability as a director (only the distributor came out rather unharmed). The flop of this film (as well as that of The Long Kiss Goodnight, also starring Davis and directed by Harlin) is widely credited with destroying their marriage, as Harlin had pushed for Davis, then known for comedic roles, to headline the two blockbusters.
Epic Fail: A meta-example with what happened at the box office and how it affected almost everyone involved. Not only was it the biggest bomb in film history, Geena Davis's career was derailed, her marriage to the director collapsed and she never fronted a major release again. Not only that, but the director, Renny Harlin, had his career destroyed as well, and it also succeeded in sinking the company that released it. It also managed to successfully kill the swashbuckling genre for two decades until Pirates of the Caribbean came round.
Genre-Killer: Some have accused the film of being this for swashbuckling pirate movies. In reality, the genre was already dead at the time; Cutthroat Island just failed to revive it (an admittedly spectacular failure, that is). We would not see another swashbuckling pirate movie from a major studio until Disney released Pirates of the Caribbean: The Curse of the Black Pearl in 2003, and more than a decade afterwards the genre is still devoid of major titles not belonging to said franchise.
Renny Harlin and Geena Davis, who had a reasonably successful marriage and creative partnership at the time, began to explore the possibility that she might be able to expand from the light comedies she'd made her name with to action movies. A pirate movie seemed like a good place to try to start.
Michael Douglas conditioned his appearance on getting an equal amount of screen time as Davis. After he began to suspect the filmmakers were adding scenes for her without letting him know, he quit. Many other prominent male stars turned it down before Matthew Modine took the part. While it was partially a boon to the producers in that he actually knows how to fence, he was also not the first or even the 17th person you'd think of for an action-adventure swashbuckling male lead at the time.
Due to the casting distractions, 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.
Oliver Reed had been cast as Mordechai "Fingers" Adams, but had to be replaced after (surprise!) he got drunk and flashed Davis on the set. By that time Davis and Harlin had lost any enthusiasm they had originally had for the project and were strictly in it because they were contractually obligated. And they were getting paid.
Matthew Modine several years later went on record to explain some of the reasons why the film's costs spiralled 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 Harlin and 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.
Broken pipes caused raw sewage to pour into the water tank where the actors were supposed to swim.
The less than $10 million the film made at the box office against a budget over ten times that led to cascading Creator Failure: Carolco, the studio, went bankrupt. Harlin and Davis tried one more film together, The Long Kiss Goodnight, and then called it a marriage. She hasn't been the A-list lead she was before then, and his projects since have mostly been low-budget genre films. The film is also blamed for killing the pirate movie until Pirates of the Caribbean. Although it's more accurate to say it failed to relaunch the genre, since there hadn't been many made before it.
Meryl Streep was also very, very close to playing the part of Morgan but had too much of a busy schedule to work it in.
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.