It is tempting to hanker after a simpler, more stable and predicable if not golden age in schooling, when administration and management were predominantly the responsibility of the principal or head teacher, and almost everyone else in the schoolhouse got on with the business of teaching. Alas, a very different tune in more recent times has been popularised by policy-makers and researchers alike, and in many contexts the polyphony has been embellished, enhanced, adapted and embraced by principals and their colleagues. However, many practitioners assert that the research community continues to add dimensions to leadership, to expand the score while deleting nothing, thus, by default or by design, and looked at from the principal’s perspective, only the heroic need apply! Some commentators may even suggest that expanding leadership agenda contributes considerably to the decline in interest in the principal position. Against this general backdrop and set of considerations, the paper seeks to distil from selected literature identifiable continuities that traverse some conceptualisations over time, while seeking simultaneously to document distinctive features underneath the chameleon’s camouflage. On the premise that concepts are bound by time and place, products of culture, the paper begins with the mythic and heroic, and situates this within organisational change and school reform literature, while taking a Herculean-Achilles perspective, identifying strengths and weaknesses, thus seeking to indicate that as the project of school reform/ school effectiveness/ school improvement has taken on various hues, collaboration has been supplanted by teacher and distributed leadership. While following the trajectories of these concepts, the paper documents and puts in perspective the commonalities and differences of these concepts while also seeking to document and understand their dominant shaping influences, a product of international social movements. Part of the argument presented is that without such a situated perspective, key aspects of new and emergent concepts remain poorly understood, superficially adopted, thus perpetuating cycles of fashionable adornment more than sustainable change.