2. Psycho (1998)
As bizarre career choices go, this one is way up there. In 1998, Gus Van Sant was at the height of his powers following the multi-Oscar winner Good Will Hunting. Credit where it's due, the director did not want to follow the most obvious path, and so for his next film, he embarked on a remake of Alfred Hitchcock's iconic 1960 classic. This alone took some nerve; but also, rather than updating it for the modern day, Van Sant made the curious decision of literally remaking the exact same movie shot for shot, with an almost identical script. It's in colour, blood and nudity are shown, and some references are contemporised, but otherwise it's literally a direct facsimile of Hitchcock's film. As an experiment in film-making, there may be a certain merit to what Van Sant and company achieved. Overall, though, it's hard not to wonder what in the world they were thinking.