“Generation” is a twofold term. Understood as generational identity (generationality) the history of “generation” can be traced back to its foundational moment during the First World War. In its second meaning, as genealogy, the idea of generation is age-old. While sociological and historical research tends to focus on generationality, literary and cultural studies have recently reinvigorated the study of generation as genealogy. Both concepts are deeply enmeshed with literature and other representational media. Such entanglements point well beyond our field’s traditional practice of using the notion of generation as a means of writing literary history (from the “first-generation Romantics” to the “angry young men”). What is at stake, rather, is the development of comprehensive and conceptually rigorous approaches to the many-layered interrelationships between generation, memory, and literature. “Generation” deserves to be put on the agenda of a “new” literary history. This article therefore proposes an integrative literary- and memory-studies perspective on generation, combining classic and more recent theories of generation with historical case studies. It reconstructs three discursive constellations around “generation” that have shaped the past century (the First World War and the “lost generation,” the Holocaust and the “generation of postmemory,” and the nexus between immigration and generation) with a focus on the question of how literature and literary studies have intervened in these discourses. It does so in order to show the rich, and still largely untapped, potential of studying generationality and genealogy as part of literary history.