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Pain, and toothache in particular, belongs to the most basic human experiences. This paper describes how the experience of pain is shaped and modified by individual human minds and by specific medical cultures. It explores what social historians of medicine call the historical, social, cultural, and psychological construction of pain. The story of how people reconstruct the experience of pain in past and present demands that we look beyond the medical gaze. The voices most often neglected in medical history belong of course to patients. However, their testimony is difficult to recover, except for more recent times. We have to look therefore for their hidden voices in diaries, memoirs, essays, poems, novels and other literary genres. These scattered records and fragmentary episodes of bouts of illness suggest that the history of toothache cannot be reduced to a parable about biomedical progress, but stands at the crossroad of bodies, minds, and cultures.