Cutthroat Island – $89 million
Cutthroat Island is a movie about pirates. But, unlike Pirates of the Caribbean, Cutthroat Island ended up losing $89 million after the two-hour film only raked in $10 million at the box office. This movie came out in 1995, so it set a pretty low bar for subsequent pirate movies.
In fact, Cutthroat Island did so poorly that it made the Guinness Book of World Records for being the biggest box office flop in history. Roger Ebert gave it three stars out of four but said that it wasn’t a “necessary movie” since there was absolutely nothing unique about Cutthroat Island. The production studio, Carolco Pictures, went belly-up after the movie bombed.