Writing the New Twenties is a critical investigation of the 2020s through a comparative study with a transformative decade for American literature and culture, the 1920s, also referred to as “the twenties.” Both decades present signs of major social change and transformative innovation, providing raw material for social tension, artistic creativity, and intellectual novelty. The “new twenties” are characterized by stark contradictions, as the proliferation of media is questioned by the rise of disinformation, while the emergence of new voices of American literature is undercut by threats to freedom of speech and fear of prosecution. Contributing authors trace these parallels across aesthetic forms, ranging from intermedial life writing and competing autobiographical renderings of the 1920s, to contemporary multimodal narrative experiments and current considerations of what it means to “make it new.” This special issue draws attention to the points of convergence between the 1920s and the 2020s as decades of transformative change and intense creativity, as well as chronicles our initial understanding of the present moment in American literature, history, politics, and society.