BackgroundIn a pain drawing (PD), the patient shades or marks painful areas on an illustration of the human body. This simple yet powerful tool captures essential aspects of the subjective pain experience, such as localization, intensity, and distribution of pain, and enables the extraction of meaningful information, such as pain area, widespreadness, and segmental pattern. Starting as a simple pen-on-paper tool, PDs are now sophisticated digital health applications paving the way for many new and exciting basic translational and clinical applications.ObjectiveGrasping the full potential of digital PDs and laying the groundwork for future medical PD apps requires an understanding of the methodological developments that have shaped our current understanding of uses and design. This review presents methodological milestones in the development of both pen-on-paper and digital PDs, thereby offering insight into future possibilities created by the transition from paper to digital.MethodsWe conducted a systematic literature search covering PD acquisition, conception of PDs, PD analysis, and PD visualization.ResultsThe literature search yielded 435 potentially relevant papers, from which 53 methodological milestones were identified. These milestones include, for example, the grid method to quantify pain area, the pain-frequency maps, and the use of artificial neural networks to facilitate diagnosis.ConclusionsDigital technologies have had a significant influence on the evolution of PDs, whereas their versatility is leading to ever new applications in the field of medical apps and beyond. In this process, however, there is a clear need for better standardization and a re-evaluation of methodological and technical limitations that no longer apply today.