Adrienne Miller got her lucky break when she was hired as an editorial assistant at GQ magazine in the mid-nineties. Even if its sensibilities were manifestly mid-century, GQ still seemed the red-hot center of the literary world. It was there that Miller began learning how to survive in a man’s world. Three years later, she forged her own path, becoming the first woman to take on the role of literary editor of Esquire, home to the male writers who had defined manhood itself— Hemingway, Mailer, and Carver. But this was also a unique moment in history that saw the rise of a new literary movement, as exemplified by McSweeney’s and the work of David Foster Wallace. A decade older than Miller, the mercurial Wallace would become the defining voice of a generation and the fiction writer she would work with most. Their intellectual and artistic exchange grew into a highly charged professional and personal relationship between the most prominent male writer of the era and a young woman still finding her voice.