On an inflation-adjusted basis, Cutthroat Island (1995) continues to be the biggest box-office flop in history. While that distinction alone may be worthy of the top position in my countdown, I just couldn't rank it higher than #3. In particular, the film lacked true star power and suffered from its studio's financial difficulties. For me, those qualifications make it less bust-worthy. At the same time, I recognize that the damage created by the movie's wake has been significant. Of note, the director (Renny Harlin), lead actress (Geena Davis), and lead actor (Matthew Modine) all have been relegated to the small screen. If you don't recognize those names, you now know why.