Chapter 4 examines the rise and evolution of hypertext fiction, from classic works such as Michael Joyce’s afternoon: a story (1987) through to early twenty-first century works, including Shelley and Pamela Jackson’s The Doll Games (2001). The analysis provides the second axis to the author’s analytical framework, namely, longitudinal and historical, charting the development of hypertext fiction from postmodern disorientation to the affective earnestness of metamodernism. The chapter argues that Mark. Z. Danielewski’s House of Leaves was one of the first printed novels to explore a new kind of transmedial hybridity, positioning the physical book within a network of paratextual digital material. At the same time, hypertext works such as The Doll Games (2001) and William Gillespie, Scott Rettberg and Dirk Stratton’s The Unknown (1998) embraced new fusions of participatory and performative storytelling.