This paper aims to analyze the concept of the Lost Generation as presented in the novelistic re-writings of the lives of the great American authors, F. Scott Fitzgerald and Ernest Hemingway. Their life stories are repeatedly used as plot lines in postmodern biofictions, which underline the connection between fiction, biography, and autobiography by developing texts that are “both self-reflexive and yet paradoxically also lay claim to historical events and personages” (Hutcheon, 2003, p. 5) These stories inherently carry the information about the time and places where they lived while the creative process involves specific textuality to genre-blending, makes use of different facts, fictional characters, literary works and practices, themes and subjects, which are re-ordered in a constantly changing world of doubling, mirror reflections and fluctuations constructing concepts of the time and culture in a literary form from a most recent perspective. The Lost Generation is one such concept that forms a constitutive part of these narratives, allowing for the plausibility and uniqueness of the story. This paper unravels the notions of the Lost Generation in the biofiction genre and the techniques used for that portrayal. The biofictional rendition is especially relevant, marking a hundred years since the establishment of the concept of the Lost Generation and the understanding of it in the contemporary world.