Ancient Greece has been represented in cinema several times over the years and has received mixed reviews, unfortunately primarily negative. The genre appears to have fallen behind the dark shadow of Rome and perhaps with good reason. Despite any failures that filmmakers have made along the way, films based in antiquity continue to be popular for they possess the ability to bridge the gap between the past and the present, offering spectacular and compelling interpretations of history that are both relevant and educational for viewers. This can be said for both Greek and Roman history, yet what is it about Greek history that seems so difficult to portray on screen? Evidently, there are three primary issues in regards to filming Greek history in a manner that modern audiences will be able to both understand and connect with: the problem with “Greek love;” the lack of unity within ancient Greece; and the difficulty of filming key “Greek” ideas. The famous tales of the battle of Thermopylae and Alexander the Great have emerged as the most “successful” Greek stories to be represented in film, however, they are not without fault. By examining how filmmakers have addressed the issues of representing Greek history through films such as Alexander the Great (1956), Alexander (2004), The 300 Spartans (1962), and 300 (2007) the success and failure of each will be identified as well as how such films may mark a shift in this trend of unpopularity.