The concepts of what a toy is and what play as a phenomenon represents, evolve. This paper examines how play is affected by digital toys and toy robotics, conceptualized here as play machines. The position paper offers pluralistic perspectives on play machines in an era heading towards a post-digital state by combining earlier research on the historical trajectory of mobile toys with current developments in interactive toys. The paper reconceptualizes toys as interactive media connecting with thingness, transmedia, and technology as perspectives on the toy medium. Finally, the paper illustrates the connections between an emerging category of toys, Internet-connected character toys, and companion robotics, which in speculative toy fiction emerge as future ‘toy friends’ or Artificial Friends, offering enriched possibilities for motion and emotion in player engagement.