Pain is an evolutionary and adaptive mechanism to prevent harm to an individual. Beyond this, how it is defined, expressed, and borne is dictated culturally. Thus, the study of pain requires a holistic approach crossing cultures, disciplines, and time. This volume explores how and why pain-inducing behaviors are selected, including their potential to demonstrate individuality, navigate social hierarchies, and express commitment to an ideal. It also explores how power dynamics affect individual choice, at times requiring self-induced suffering. Taking bioanthropological and bioarchaeological approaches, this volume focuses on those who purposefully seek pain to show that, while often viewed as “exotic,” the pervasiveness of pain-inducing practices is more normative than expected. Theory and practice are employed to re-conceptualize pain as a strategic path towards achieving broader individual and societal goals. Past and present motivations for self-inflicted pain, its socio-political repercussions, and the physical manifestations of repetitive or long-term pain inducing behaviors are examined. Chapters span geographic and temporal boundaries and a wide variety of activities to illustrate how purposeful pain is used by individuals for personal expression and manipulated by political powers to maintain the status quo. This volume reveals how bioarchaeology illuminates paleopathology, how social theory enhances bioarchaeology, and how ethnography benefits from a longer temporal perspective.