16. Citizen Kane
It is almost impossible to discuss the history of a film without touching on Orson Welles’ masterpiece Citizen Kane. The drama, which portrays the life of a thinly veiled William Randolph Hearst figure named Charles Foster Kane, was filmed using many new and revolutionary techniques that would later become standard in filmmaking. The film’s length, superb quality, and experimental style have long caused it to be ranked as the greatest film ever made. Despite this, Citizen Kane lost the Best Picture award to John Ford’s How Green Was My Valley.