The aim is to highlight what kind of play and learning is constituted in situations where preschool children are involved in activities with digital media. This paper presents the results from a research project of children encountering computer tablets in preschool settings. The study is located in a contextual perspective on play (Edwards, 2013), building on earlier studies of digital play and learning (Plowman, McPake & Stephen, 2008) and of digital media and popular culture (Gutnick, Robb, Takeuchi & Kotler, 2011). The theoretical framework for this study draws upon a sociocultural perspective on play and learning (Vygotsky, 1933; Wertsch, 1998), as well as the perspective on participation as a process where both activity and to join in a social practice are components (Lave & Wenger, 1991; Wenger, 1998). Two Swedish preschools with a total of 35 children aged 3- 5 years old participated. The material consists of video recordings followed by interaction analysis. Ethical standards were assured through written informed content by all parents and personnel, and oral consent from the participating children. Main findings show that within this specific context both play and learning takes place in parallel in relation to closeness and distance: on one hand in form of joint activities and mutual enjoyment, and on the other in form of struggle of power and strategies for cheating. Finally, in the children's activities with digital media, popular culture is abundantly present as a facilitator for play and learning, hence should be taken into account in the didactical practice.