Charles's feature debut was "Masked and Anonymous" (2003) which he directed, and co-wrote with Bob Dylan (under the pseudonyms Rene Fontaine and Sergei Petrov, respectively). The film received a mixed reaction from audiences and critics alike; it did poorly at the box office. Charles maintains it takes many viewings to get true enjoyment from the film: "I want the movie to be like a great Bob Dylan song that is listened to over and over and for people to back and see it again and get a lot more things, or totally different things."