This chapter features the contributions of influential and lesser-known essayists who have written persuasively and engagingly on gender and sexuality in the twentieth and twenty-first centuries. Issues of identity and difference have had a profound effect on the writing of our age, and certainly on the essay, the most elusive of genres. This chapter considers the intersections of the essay, gender, and queer studies/consciousness over the last few decades, first in a general sense, and then through the lens of specific essayists who have had the most significant impact on the direction of the essay since 1970 in the United States. Beginning with second-wave feminism, this chapter discusses the work of those essayists in feminist and LGBTQ+ communities whose foundational writing on gender still resonates today. The chapter examines important essays that emerged from third- and fourth-wave feminism and then pursues the stylistic and thematic innovations brought by lesbian, gay, trans, and queer writers who have explored topics such as gender as performance, HIV and AIDS, misogyny and misandry, intersectionality, discrimination, and the medicalization and mediatization of desire.