Working at the intersection of literature and history that is fundamental to medieval studies, this dissertation joins the ongoing reevaluation of Richard II’s reign by putting his reign into conversation with its literary intertexts and literary afterlives. I argue that viewing Richard II’s reign through a queer lens that is informed by Lee Edelman’s idea of reproductive futurity better contextualizes the critical tensions which have long existed around Richard II’s sexual orientation as well as the ongoing affinity queer subjects have had for the king in twentieth- and twenty-first century literature and performance. Overall, I assert that while Richard II can be understood as queer, his queerness comes from a lack of engagement with the logic of reproductive futurity rather than any particular sexual or romantic object choice. I first look at Richard II’s literary contexts and intertexts as I discuss the cultural norm of royal fecundity evident in insular romance, including Octavian, Sir Tryamour, Sir Eglamour of Artois, Havelok the Dane, and The Marriage of Sir Gawain and Dame Ragnelle. This context reveals the obviously missing children in Troilus and Criseyde and the documents and chronicles of Richard II’s reign, allowing us to see that Richard II’s heirlessness was tied to perceptions of his lack of manhood in a way that can be seen as queer. His queerness was, in my assessment, a fundamental part of why he struggled to maintain his power and assert his majority, and a fundamental part of why Richard II’s history has often been viewed as fated. Because of his queerness and the normalizing forces of history, Richard II’s literary intertexts, as seen in my examination of Richard Maidstone’s Concordia create queer experiences of temporal asynchrony for readers. Further, it is through an affinity for the struggles he endured because of his sexuality that there has been a queer affinity for the subject of Richard II across time, as facilitated by productions of Richard II, and as seen in texts such as Richard of Bordeaux and Plague Over England.