This study delves into the critically uncharted world of edutainment podcasts, specifically those that turn to historical narratives for their content. Through analysis of two case studies, a pair of topics covered by four edutainment podcasts, it explores the ways in which educational or informational aims may be shaped, for good or bad, by an entertainment mission. The topics are drawn from the often disturbing field of medical history, a common choice for edutainment podcasts but a source of content that repels as much as it attracts, presenting a challenge to creators attempting to balance learning and diversion. The study finds that the audio format is both a help and a hindrance to this process, but the most important factor in these podcasts’ structure and relative success or failure may be their dialogic nature.