4. Easy Rider
The film that defined its generation does not hold up because it is exactly the film that defines its generation. It so perfectly encapsulates its time that for todays viewer it is quite dated. It is a representation of hippie, nonconformist culture and it is structured in the way a nonconformist would structure it. With today, it feels like travelogue through the road as psychedelic rock plays throughout the film. Easy Rider is quite a bizarre film. Made by Dennis Hopper, it was not unusual for him to be on some sort of narcotic during the filming leading to some of the strange characterizations. In a modern way of looking, this is quite a pretentious film in which Hopper and Fonda stroke their egos as they pursue Fondas hobby of riding. The making of the film seemed to make a much more interesting film than the results as it dealt with the contentious Hopper with his crew, actors which included knives being pulled and actors pretending to talk to his dead mother.But, its influence on New Hollywood and the way it broke the greatest actor of that generation, Jack Nicholson, leaves a significant mark on our culture.