Exact statistics are hard to come by, but some estimate that 1 in every 250 people self-mutilate, primarily young women. Often medically described as Non Suicidal Self Injury (NSSI), self-harm includes biting, bruising, burning, scratching, scraping, hitting and, perhaps most well-known, cutting. This chapter addresses how self-harm in art sophisticatedly developed from harming oneself in the name of art to thoughtfully exploring the nuances of the disease, particularly including the psychology of the illness. Beginning with early extreme performance artists Ulrike Rosenbach and Vito Acconci, quickly artists such as Lisa Steele, Cynthia Maughan, Barbara T. Smith and Nancy Buchanan, Sanja Iveković, and Kiki Kogelnik move beyond creating pain in art to exploring the context of harming in art. Marking or writing on the flesh can recall self-harm practices of cutting, scratching, and marring the flesh. Photographers Jo Spence and Catherine Opie as well as painter Jenny Saville utilize the strategy to comment on issues of health and insecurities about body size. Gina Pane, Marina Abramović, and Kira O’Reilly force a confrontation with the actual act of cutting and self-harm by actually performing the self-mutilation in front of an audience. Yet they are still lacking the connections to the specificities of NSSIs. Emerging artists Laura Hospes, Chen Zhe, and Kristina E. Knipe turned to their cameras to document experiences being institutionalized, fresh injuries, painful scars, and conversations that directly address mental health. By examining the range of self-harm techniques and strategies, the deeper prevalence of NSSIs become very clear, and in drawing more attention to these concerns, can they be fully understood and helped.