For many contemporary artists, failure has been an instrument of experimentation and self-expression, of investigation into existential questions and manifestation of utopian tensions. In this paper, I will discuss how some of the well-known strategies of experimental and avant-garde artistic practices with failure involve risky actions, challenging or impossible attempts, loss of control, and compulsive repetition of inconclusive acts. In those experimentations, the ideal model of an effective and successful action performance (in which a goal is defined through a clear intention, a plan and a well-controlled execution) is willfully sabotaged in its stages. In this regard, a distinction between failure and mistake will be highlighted: if failure could be traced back to the tradition of heroic or tragic defeat in front of adverse odds, mistake on the contrary means doing something wrong that one is expected to control. While failure negatively reflects our tension toward autonomy, the focus on mistakes is the expression of rigidity and heightened risk aversion in contexts where maximal efficiency and self-optimization are expected. This paper will argue that equating the category of failure with that of mistake is not faithful to the motives underlying those artistic traditions. In this respect, artistic experimentations in the “aesthetic of failure” can also be viewed as a critical response toward a general mindset defined by the anxiety of control and obsessive mistake avoidance that seems typical of our current times.