The SPIE Passive and Active Millimeter Wave Imaging conference has provided an annual focus and forum for practitioners in the field of millimeter wave imaging for the past two decades. To celebrate the conference's twentieth anniversary we present a historical review of the evolution of millimeter wave imaging over the past twenty years. Advances in device technology play a fundamental role in imaging capability whilst system architectures have also evolved. Imaging phenomenology continues to be a crucial topic underpinning the deployment of millimeter wave imaging in diverse applications such as security, remote sensing, non-destructive testing and synthetic vision.