- Awesome Music: The entire soundtrack is probably John Debney's best as well as one of the top modern swashbuckling film scores - or just top film scores, period. A number of veteran film score collectors consider it even superior to the music from Pirates of the Caribbean. To note how those notions translated to objective success, Debney was just about the only participant in the film whose career actually benefitted from working on it - he remains a prolific, in-demand composer to this day.
- Complete Monster: Douglas "Dawg" Brown is the Black Sheep of the Adams pirate brothers and the captain of the ship Reaper. Each of the four brothers has a piece of a map to a fabulous treasure and Dawg wants it all to himself. The first thing we learn about him is he murdered one brother and has another hostage to murder after he gets his piece of the map. When his brother gives his map to his daughter Morgan, Dawg stops at nothing to kill his niece. He attacks his last brother Mordecai and threatens to run him through if Mordecai doesn't give up the map. When a luckless mook accidentally falls into Mordecai and impales him on Dawg's knife, Dawg kills the man growling that he killed Dawg's brother, though he's only angry Mordecai died before Dawg got the map. He tries to torture Morgan by trying to let an eel eat her face, guns down a crewman when the man complains they're running out of food and stops at no crime short of trying to steal the treasure from Cutthroat Island.
- Critical Backlash: The film is one of the biggest box office bombs ever and the film credited with the sinking of the pirate flick genre, so it is natural that many people who have watched the film consider it at least not as bad as to deserve such a dishonor. In fact, there are quite a few who have come to believe it's actually a genuinely good movie regardless of the economic mismanagement and production troubles that led to its failure. Roger Ebert of all people was among those; at the very time of the film, while most professional critics were panning it, he gave it three out of four stars, the same number he would give years later to Pirates of the Caribbean: The Curse of the Black Pearl.
- Before blowing away her uncle, Morgan lets out a cringeworthy Pre-Mortem One-Liner.Morgan: Bad Dawg.
- "Dawg" in itself is a pretty stupid name for a bad guy anyway. You could get away with it for a random henchman, maybe, but for the Big Bad? Not so much.
- The overly glorious and over-the-top music, especially those moments featuring Ominous Latin Chanting or some variant thereof, makes the comparatively mundane onscreen events seem almost parodic. Spoony, in particular, argued it.
- Geena Davis's performance. As Lindsey Ellis puts it, she comes across less as "bloodthirsty pirate queen", more as "Cool Aunt taking some kids to an R-rated movie."
- During the final battle, one of the pirates is actually providing background music using a violin.Captain Long John Thomas: Bloody hell, this movie has become a self-parody at this point!
- Before blowing away her uncle, Morgan lets out a cringeworthy Pre-Mortem One-Liner.
- Narm Charm: Even at its worst, the film is not difficult to enjoy. Its corny and sometimes weird dialogue, its magnificent and almost literally too good soundtrack, and the mix of acting glee and spirited incompetence by the cast all together can be rather endearing.
- So Okay, It's Average: Watching the film without any of its historical background in mind can easily give the impression that it's just a small step away from being a legitimately decent movie. Everything — the action, the humour, the dialogue, the romance, the characters — is generally okay, sometimes even good, but they carry something that make them seem just a bit... off. It might be the subtext of its Troubled Production, the inexperience of some cast members, or simply that the genre Cutthroat Island buried was certainly dying by itself and it didn't translate well to the cinema style of The '90s. The only thing that totally works is John Debney's score, which is phenomenal - in fact, some people have said it's actually too good, as in so epic that the movie can't live up to it, and draws attention to how mediocre everything else is.
- Took the Bad Film Seriously: Both the My Year Of Flops review and The Nostalgia Chick review credit Frank Langella for trying his best to save the movie despite a conspicuous lack of effort from everyone else. Of course, to hear Langella tell it, he wasn't trying to save the movie... he was just having a fantastic time playing pirates.
- They Wasted a Perfectly Good Plot: General consensus on the movie is that there's a good story in there somewhere, behind all the messy rewrites, awful dialogue, and giant explodey setpieces. The characters of Morgan Adams and William Shaw could have been delightful if handled by a more talented crew, and the idea of a movie about a female pirate could have been amazing and genre-changing if it had been done competently. Sadly, the movie's massive financial failure and talented cast stand mostly as a monument to things that could have been better.
- Vindicated by History: To a degree. While definitely not a Cult Classic, the movie has its fans today.
YMMV / Cutthroat Island