Dreaming Kester displays the conflict of childhood dreams and innocence versus adult responsibilities and realities. Its attempt to do so is admirable. However, it failed to do so entertainingly. The film is mired with playful imaginations by Kester that are not playful to the eyes of the viewer. Kester's imaginations are not humorous enough, entertaining enough, and are littered with monotonous dialogue from both the narrator and Kester himself.