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.
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.
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. 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.