The research aims to deepen Robert Smithson’s theoretical study in relation to the concept of entropic landscape during the first years of the Land Art and the consequential impact on today’s concept of image. The late 1960s was the time of feminism, of worker and student uprisings in Europe and in the US, of Cold War, of the first satellite image of Earth. In this context, environmental art represented a radical shift in the use of the image in art: isolated artworks, such as Spiral Jetty and Dissipate, changed our point of view. The project explores and interrogates the reflections and successive considerations on landscape and image that the artist developed during his career. The main topic is critique and analysis of landscape through visual art. These experiences inaugurated a new and avant-garde approach: the aesthetics of the entropic, which leads to a form of socio-political debate that will be analysed through photography and video. The idea of an art that builds a new vision reflects the collective action toward reality, simultaneously expressing the landscape condition and the current entropic, instead of resolving it in the form of an object belonging to an armoured dimension. This change of cultural and visual coordinates found absolute consensus in the words of Simmel when he refers to painting and frame: true line between the contingency and the absolute.