Matthew Modine, Geena Davis, 1995
Was Cutthroat Island ahead of its time? Eight years before Disney made franchise gold with their Pirates of the Caribbean, this swashbuckling flick sank to the bottom like so much cannon fodder. Then again, the movie didn’t have Johnny Depp doing his best Keith Richards. Oh yeah, and it was terrible. Michael Douglas had originally signed on to play opposite Geena Davis, but Douglas dropped out, leaving the film with little star power to shoulder its bloated-by-1995-standards $115 million budget. The film is the all-time biggest inflation-adjusted box-office bomb, loosing a cool $147,157,681.