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Although in countercurrent, we can identify some contemporaneous artists who share a concern for the problematization of the category of obsolescence, which goes through the significant updating of these matters in the present, throughout an anamnesis to the various historical meanings of these forms. We intend in this research note to examine the theoretical procedures that this significant updating of the obsolete is connected, namely the thought of Walter Benjamin (method of dialectical images) and his conceptualization of the surrealistic practices. Finally, we will try to clarify how obsolescence translates into a fundamental category for what Rosalind Krauss defines as the reinvention of medium “specificity” in contemporaneity, as a way for the critical positioning of artistic practices in light of the increasingly prevailing dictates of capitalism and its effects on the artistic domain, thus being a fundamental reinvention for the assent of a sphere of artistic and political freedom.