Gender issues have been a persistent topic of investigation in European culture for more than a millennium. Today, perhaps no topic is of more immediate interest to students and scholars than sexual identity. If earlier eras imagined the categories of male and female as fixed, our own age has come to believe that notions of gender are, to a considerable extent, constructed by society and thus necessarily unstable. Using current understandings of sexuality, the contributors to this collection examine afresh such diverse works as Augustine’s Confessions, the Old English Beowulf, the French Richard Coer de Lyon, German mæren, Chrétien’s Yvain, writings by Wyclif and other Lollards, the poetry of Aemelia Lanyer, and an Italian portrait by Leonardo da Vinci. As the authors of this collection demonstrate, these thinkers persistently challenged the status quo, questioning assumptions felt as facts. In turn, they demonstrate how the medieval and Renaissance writers who are the subject of these essays helped prepare the way for understanding masculinity and femininity as masculinities and femininities.