Driven by the operational needs of modern warfare, the helmet-mounted display (HMD) has matured from a revolutionary, but impractical, World War I era idea for an infantry marksman’s helmet-mounted weapon delivery system to a sophisticated and ubiquitous display and targeting system that dominates current night warfighting operations. One of the most demanding applications for HMD designs has been in Army rotary-wing aviation, where HMDs offer greater direct access to visual information and increased situational awareness in an operational environment where information availability is critical on a second-to-second basis. However, over the past 40 years of extensive HMD development, a myriad of crashworthiness, optical, and human factors issues have both frustrated and challenged designers. While it may be difficult to attain a full consensus on which are the most important HMD design factors, certainly head-supported weight (HSW), exit pupil size, field-of-view, image resolution and physical eye relief have been among the most critical. A confounding factor has been the interrelationship between the many design issues, such as early attempts to use non-glass optical elements to lower HSW, but at the cost of image quality, and hence, pilot visual performance. This paper traces how the role of the demanding performance requirements placed on HMDs by the U.S. Army aviation community has impacted the progress of HMD designs towards the Holy Grail of HMD design: a wide field-of-view, high resolution, binocular, full-color, totally crashworthy system.