In his monumental The Legends of the Jews, which attempted over a century ago to paraphrase the entirety of ancient rabbinic interpretation of the Bible, Louis Ginzberg incorporated a detail into his presentation of the Joseph narrative that likely took most early 20th Century readers of the Bible by surprise: “…there was something boyish about Joseph. He painted his eyes, dressed his hair carefully, and walked with a mincing step.” This description bears closer scrutiny; how did such an interpretation come about? Moreover, why should or would such behaviors be considered “boyish”? My paper begins with the rabbinic traditions that underlie Ginzberg’s paraphrase, and continues with a close reading of other ancient and early medieval rabbinic texts that incorporate similar themes with respect to the character of Joseph. Each of these rabbinic interpretations present the biblical narrative as manifesting an unconventional gender dynamic. I will also examine several biblical texts in which an unconventional gender dynamic may be present. While it is true that these biblical and rabbinic texts ran contrary to the normative ideational and behaviorally prescriptive traditions concerning sexuality presented by the main body of biblical and rabbinic texts, it is nonetheless true that the texts I examine invite readers to see an alternative dynamic through their stories. Finally, I will consider methodologies through which one might most profitably examine the rabbinic texts I present.