This chapter explores how twentieth-century feminist and LGBTQ+ literature deconstructs and reimagines gender in formal experimentation and genre-bending. It proposes that this literary tradition contributes to a larger cultural conversation that tends to think in binaries: trans vs. queer, gay vs. straight, male vs. female. The work of a diverse group of writers-- Djuna Barnes, June Arnold, Bertha Harris, Armistead Maupin, and Leslie Feinberg—reinvents conventional understandings of gender in forms that range from avant garde experimentation to popular and autobiographical novels. Genderqueer American writers remind us that the complexities of gender and sexuality always exceed our attempts to describe them. When we incorporate genderqueer texts by queer American writers into the larger conversationwe can access another theoretical language, one written within contingency and resistance.Only radical reimagination and continual (re)creation can ever hope to approximate the complex play and multiplicity of genders.