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‘When the people of the world all know beauty as beauty, there arises the recognition of ugliness,’ observed Lao-Tzu, the sixth century BC Chinese philosopher. Impossible apart, ugliness and beauty are antonyms and have common elements. Some people are uncomfortable talking about or attempting to define ugliness, the kind one can see. Some deny it exists, but pretending that ugliness does not, when experience and mirrors tell those who are physically unattractive otherwise, denies their experience, existence, pain, and transcendence. While the history of human ugliness and its related topics, the deformed and monstrous, has been explored in the visual arts and in literature, and studies conducted about body dysmorphic disorder, deformity, and looksism are common, actual in-depth qualitative research about how ugly men and women live their looks is not. This chapter, emerging from thirty years of sociological research as well as extensive interdisciplinary research across the humanities, social sciences, and medicine, redresses the problem. It focuses on case studies of women and men whose lives confirm their ‘ugliness,’ while contextualizing their experience through the lenses of identity, culture, history, gender, religion, and politics. The ugly provide a spectacle for others, just as the beautiful do. Theynd learn that their appearance can become a focal point that disrupts interactional flow. Using the philosopher Charles Horton Cooley’s concept of the ‘looking glass self,’ as well as other social learning and symbolic interactionist theories such as labelling theory, stigma, and the presentation of self, the chapter provides case studies of documented ugly men and women who freely admit to that status.