Remember when Geena Davis was in every movie? And remember when action maestro Renny Harlin ('Die Hard 2') was the Michael Bay of his day? Well, this infamous pirate movie put the kibosh on both their careers.

Its epic failure (only grossing $10 million after accruing a $90 million budget) is also responsible for the folding of Carolco Pictures, the one-time motion picture biggie behind the 'Terminator' movies. And when you factor in inflation, 'Cutthroat Island' is considered to be the biggest box office bomb of all time losing over $147 million. It would be years before Johnny Depp and Disney resurrected the pirate genre on the big screen.