This paper examines Vygotsky's conception of play as a leading activity in the contexts of children's contemporary play worlds. Commencing with an examination of the relationship between leading activities and the development of psychological functions, the paper moves into a consideration of the relationship between imagination and reality as a basis for play as a leading activity. The relationship is considered in the context of current discussion regarding the sociology of childhood and the sociology of consumerism to explore the ways in which children's experiences in digital-consumerist contexts possibly shape learning and development. Drawing on the example of the highly popular character Thomas the Tank Engine[TM], the paper examines the implications associated with understanding play as a leading activity within contemporary contexts, and how these might relate to existing perspectives on play, pedagogy and curriculum in early childhood education settings.