Insecure, Awkward, and #Winning: Intersectionality of Race, Gender, and Sexuality in the Works of Issa Rae is the first project dedicated exclusively to Issa Rae and her works. Her work offers a fertile space where contemporary issues intersect, encouraging audiences to discuss meaning and impact within their own lives, society, and cultural identities. The text offers analysis informed by Critical Media Studies, Cultural Studies, Critical Race Theory, and Intersectionality research. The book features a collection of provocative contributions from scholars from multiple disciplines-including literary, history, and communication. The project offers varying perspectives on Rae, insecure, her memoir, The Misadventures of Awkward Black Girl, and the relevance of her work to American culture. Throughout the book are dispersed brief reflections from veteran scholars, content creators, and industry professionals on the significance of Rae and her work. These pieces speak to the impact of Rae's cultural productions. The book contains five thematic sections that include a total of twelve chapters. Those chapters address a range of topics including Black sexuality, humor, gentrification, race in the workplace, White allies, and Blackness in digital spaces. The goal is to reach audiences both popular and scholarly. The authors hope this project sparks the interest of fans and those new to Rae's work. Among others, this book could be used in the following courses: Representation in the Media; Comparative Race and Ethnic Studies (in the Media); Research Seminar in Black Studies; Womanism, Black Feminist/Queer Theories; and The African American Storytellers.