* AwesomeDearBoy: Creator/FrankLangella considers Dawg to be one of his three favorite roles (the other two are [[Film/FrostNixon Richard Nixon]] and [[Film/MastersOfTheUniverse 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.
* BoxOfficeBomb: Budget: $98 million. Total box office returns: $10 million. It suffered the second largest confirmed loss in history at $89 million, $176 million in 2020 dollars when adjusted for inflation, alongside ''Film/{{The Lone Ranger|2013}}'' (which lost at least as much if not more).
* BreakthroughHit: Despite the film flopping, it got Music/JohnDebney (who mostly had been a television composer before this) noticed in the film scoring circles and launched his career.
* CastTheExpert: Creator/MatthewModine was cast partly because he is an experienced fencer.
* ContractualObligationProject: 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 Creator/GeenaDavis and Creator/RennyHarlin were contractually tied to do it.
* CreatorCouple: Director Creator/RennyHarlin and star Creator/GeenaDavis were married at the time of the film's production. They have since divorced.
* CreatorKiller: ''Cutthroat Island'' finished the already dying studio Carolco, as well as destroying Geena Davis' career and her then-husband Creator/RennyHarlin's respectability as a director (only distributor Creator/MetroGoldwynMayer and composer Music/JohnDebney came out rather unharmed, though it added to the already monstrous debt of MGM's backers, the French bank Crédit Lyonnais). The flop of this film and ''Film/TheLongKissGoodnight'' (also starring Davis and directed by Harlin) is widely credited with shattering their five-year marriage, as Harlin had pushed for Davis, then known for comedic roles, to headline the two blockbusters, only for the move to backfire on both of their faces (that and Harlin cheating on Davis with her own personal assistant and even fathering a child in her back).
* FakeBrit: American-Canadian actor Creator/MauryChaykin plays John Reed, who is from Britain.
* FollowTheLeader: This film was made after ''Film/RobinHoodPrinceOfThieves'' brought swashbuckling adventure films back on the map.
* GenreKiller: Some have accused the film of being this for swashbuckling pirate movies. In reality, the genre was already dead at the time since at least the failure of Creator/RomanPolanski's ''Film/{{Pirates}}''; ''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 ''Film/PiratesOfTheCaribbeanTheCurseOfTheBlackPearl'' in 2003, and almost three decades afterwards the genre is still devoid of successful titles not belonging to the ''Franchise/PiratesOfTheCaribbean'' franchise.
* InternationalCoproduction: The film was co-produced by Creator/CarolcoPictures and Tele-Communications, Inc. in the United States and Creator/StudioCanal in France.
* MisplacedNamesPoster: See the main Film page image.
* NoStuntDouble: Creator/GeenaDavis performed Morgan's LandInTheSaddle stunt herself.
* PlayingAgainstType: Harlin hoped this movie would turn Creator/GeenaDavis, an actress that had made her career on light romantic comedies, into an action star. It failed.
* StarDerailingRole: Not only was the film a studio-destroying disaster, it negatively affected the careers of its two stars:
** Creator/GeenaDavis achieved her breakthrough in the '80s, winning an Oscar for Best Supporting Actress in ''Film/TheAccidentalTourist'', then followed it up with her iconic turn (and Oscar-nominated role) in ''Film/ThelmaAndLouise''. Her star, however, had began to fade a few years later with ''Angie'' and ''Speechless''. ''Cutthroat Island'' was supposed to a vehicle by her then-husband Creator/RennyHarlin to reinvent Davis as an action star, but it ended up being the final straw for her A-List career after the film ended up being one of the biggest box office disasters in history. It didn't help matters that Davis immediately regretted accepting the part when it became apparent that it was doomed to fail and tried to back out, only to find she was forced to remain on the project due to contractual obligations. After this film, Davis and Harlin collaborated again on ''Film/TheLongKissGoodnight'', which fared better commercially but still lost money, and on top of that, the two divorced a few years later. Davis then retreated to television, with the occasional supporting role in a feature film.
** Creator/MatthewModine hoped that this would be his breakthrough role as the male lead, originally written for Creator/MichaelDouglas. After ''Cutthroat Island'' bombed, he returned to television, and like Davis, his film roles were relegated to supporting parts. However, he received attention for his role on the Netflix series ''Series/StrangerThings''.
* ThrowItIn: Creator/MatthewModine was hit on the head by a falling barrel during the tavern escape - the shot was kept in the film.
* TroubledProduction: Where to start?
** Creator/RennyHarlin and Creator/GeenaDavis, 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.
** Creator/MichaelDouglas 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.
** Creator/OliverReed had been cast as Mordechai "Fingers" Adams, but had to be replaced after (surprise!) he got drunk and flashed Davis on the set. By this point, Davis and Harlin had lost any enthusiasm they had originally had for the project and were strictly in it because they were [[ContractualObligationProject contractually obligated]] (and at least 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.
** There is at least [[ShroudedInMyth a legend]] that Davis "fell in love" with a small white donkey in Malta and begged Harlin to buy and fly it on a private flight to her home in Los Angeles (on the movie's budget, of course).
** Broken pipes caused raw sewage to pour into the water tank where the actors were supposed to swim.
* UncreditedRole: Renny Harlin appears as a pirate with a rifle and Daragh O'Malley portrays Bourke, but both actors are uncredited.
* WhatCouldHaveBeen:
** 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 Creator/RennyHarlin, 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.
** Creator/MichaelDouglas was initially cast as William, but decided that he wasn't getting enough screentime and dropped out. Creator/JeffBridges, Creator/GabrielByrne, Creator/RussellCrowe, Creator/TomCruise, Creator/RalphFiennes, Creator/MichaelKeaton, Creator/DanielDayLewis, Creator/LiamNeeson, Creator/KeanuReeves, Creator/TimRobbins and Creator/CharlieSheen all turned it down before Creator/MatthewModine was cast. Part of the problem may well have been that most of them were bigger stars than Geena Davis, but the story required them to play second banana to her.
** Creator/MerylStreep was also very, very close to playing the part of Morgan but had too much of a busy schedule to work it in.
** Creator/OliverReed was originally cast as Mordechai Fingers, but he was fired after getting in a bar fight and mooning at Geena Davis.
** An unused score was composed by Music/DavidArnold.