The term ‘lost generation’ evokes both the gilded decadence of the 1920s and the pulsing undercurrent of post-war disillusion, themes dominating seminal literary works of the 20th century. The writers of the lost generation were artists and intellectuals, standing on the outskirts of culture, while simultaneously creating what would become epitomes of the modern condition. For this reason, many historians argue that the lost generation is a myth. However, this claim overlooks the fact that many of the writers indeed felt ‘lost’. In truth, the term is a broad generalization that erases the complexity of the collective mood among many people, including the writers, during an age of tumult. This essay attempts to clarify the ambiguity surrounding the term Lost Generation. It begins with a documentation of the term’s origins and evolution, followed by an analysis of the autobiographies, fiction, and lives of three Lost Generation writers: Ernest Hemingway, F. Scott Fitzgerald, and T.S. Eliot. The exploration of their literary works, alongside their lives, offers an insight into understanding their worldview and whether the term ‘Lost Generation’ accurately encapsulates their sentiments. This essay further reveals nuances layered in our current understanding of the Lost Generation and shows how it is a truth in abstraction, having some resonance with the 20th century, without taking full account of the experience of American intellectuals.