This chapter begins by discussing the importance of the act of play within Jung’s analytical psychology. I present video gaming as a modern creative medium within which moments of self-reflection and aspects of individuation can occur while engaged in immersive gameplay. I focus on The Legend of Zelda franchise as the central game series due to its rich archetypal content and because it is a beloved and enduring classic among gamers old and new. I pull examples and illustrations of archetypal engagement from numerous games from within the franchise throughout the chapter. I use Campbell’s (1949) and Vogler’s (2007) treatment of the hero’s journey as a framing device for the narrative progression of the game which both the main character and the player follow. The chapter concludes with considerations of future applications of Jungian concepts to video gameplay.