What is it about the concept of a Space Shuttle that has been so inviting throughout the 20th century? A winged, reusable space vehicle for human flight beyond Earth dominated thinking about the task prior to the space age, but to compete with the Soviet Union in the human space spectaculars that began in the late 1950s the USA opted for easier to build and fly ballistic capsules. No sooner had that competition ebbed, however, than NASA returned to the pursuit of a spaceplane, resulting in the building of the winged, reusable Space Shuttle which flew for 30 years. This essay reviews the more than 40-year history of the quest for a spaceplane that eventually found fruition with the operations of the Space Shuttle and continues with current attempts to create a replacement and ensure that spaceplane dreams are kept alive. Three major lessons concerning this quest come to the fore and are highlighted in this essay: (1) the power of an idea to push engineering reality, (2) the delta between technological knowledge and potential, and (3) the reality of how critical design elements are not only fostered by hard-headed engineering analysis but also by other conventions and priorities.