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Hervey Cleckley (1903–1984) was probably among the most influential psychiatrists of the 20th century, but the history of his intellectual contributions to psychopathy is not especially well known. Not all of Cleckley’s writings have stood the test of time, but others seem prescient, arguably anticipating current debates regarding such contentious issues as successful psychopathy and the treatability of psychopathy. Although Cleckley’s seminal writings on psychopathy are familiar to many contemporary scholars, Cleckley’s role as an expert witness and his writings on other topics, such as dissociative identity disorder, may be less familiar to many readers. Cleckley’s rich and diverse body of work is worth revisiting for its keen insights regarding psychopathy and personality pathology more broadly.