In celebration of the American Psychiatric Association’s 175th anniversary, the author presents an overview of major trends in psychiatric residency education over the past 75 years, from 1944 to 2019, using narrative review and personal perspectives infused with occasional irreverence. In both 1944 and today in 2020, psychiatric educators have been challenged by having too many patients, too few clinicians, too few teachers, and too little knowledge. Over the course of these years, psychiatric residency training has adapted and evolved in response to major ongoing shifts in psychiatric practice patterns shaped by economic, social, and cultural forces, academic regulations and processes, roles for psychiatry vis-à-vis other health and mental health professions, diagnostic and scientific models, psychotherapeutic, psychosocial, and biological treatment paradigms, methods of education, and methods of educational evaluation. Trends in psychiatric education have moved from loosely and irregularly structured clinical and didactic curricula to much more highly regulated and bureaucratized program requirements and processes, from faith-based beliefs and practices to increasing reliance on evidence-based faith, from the availability of Federal funds directly supporting stipends and teachers to the disappearance of those funds, from few to increasing numbers of women entering psychiatry (and all of medicine), and persistent concerns about recruiting excellent and diverse US medical school graduates into residency. Psychiatric educators will continue to help generate, synthesize, sustain, and disseminate meaningful narratives and to prepare future generations of psychiatric residents armed with iteratively better myths and conceptualizations about human nature, purpose, and our place in the universe—and about how to better confront and reduce psychiatric suffering through psychotherapeutic, psychosocial, and biological treatment strategies. Trends are onward and upward.