In game studies, meaningful play is commonly discussed and situated through Salen and Zimmerman’s (2004) definition describing it as the integrated and discernible relationship between player actions and system outcomes within the context of the game. However, this overlooks other ways that play can be meaningful. Based on observation and interviews with 20 Australian players, this article examines experiences with death in the tabletop role-playing game Dungeons & Dragons (D&D). In the context of meaningful play ( Salen & Zimmerman, 2004 ) and positive negative experiences ( Hopeametsä, 2008 ), we discuss (1) the impact of shared physical and social realities on death in D&D, (2) the design of death in D&D, and (3) how death in D&D shapes the future play and lives of players. From this, we argue that play can have meaning that transcends game boundaries, subsequently proposing the concept of “ pivotal play” to describe appealing, memorable, and transformative play experiences.