This essay offers a comparative study of U.S. American literature in the 1920s and the 2020s through the lens of Ezra Pound’s modernist injunction to “make it new.” It examines how writers in both periods respond to moments of profound social, cultural, and technological transformation by reimagining literary form, voice, and subject matter. The analysis is divided into 4 different sections—Fragmentation and Formal Innovation; Identity and the Self; Race, Power, and the American Dream; and Time, Memory, and History—highlighting how each era negotiates the tension between continuity and rupture. In the 1920s, modernists such as T. S. Eliot, Gertrude Stein, William Faulkner, and F. Scott Fitzgerald broke with linear narrative and conventional representation to address postwar disillusionment and cultural instability. In the 2020s, authors including Claudia Rankine, Ocean Vuong, Colson Whitehead, Jennifer Egan, and Percival Everett employ hybrid forms, multimedia structures, and intersectional perspectives to confront racial injustice, climate crisis, queer identity, and the digital transformation of experience. While modernist fragmentation often sought aesthetic mastery and mythic coherence, contemporary fragmentation embraces instability as both political stance and artistic method. The essay argues that “making it new” in the twenty first century entails ethical as well as aesthetic innovation, with literature functioning as a site for historical recovery, social critique, and the rearticulation of marginalized voices. Over the course of a century, the drive to reshape persists, yet the “new” now emerges as a palimpsest—layered over inherited forms, in dialogue with the past, yet attuned to the urgencies of the present.