The Chinese pipa has long served as a symbol of traditional Chinese culture throughout its nearly two-thousand-year history. In Chinese literary, performing, and visual arts, the pipa is almost always associated with women, even though historically, both men and women played the instrument. Since the 1990s, however, the number of female pipa players has increased sharply, to the point of dominating the field in number. Despite the feminine associations and current-day dominance of women as pipa performers, women's names rarely appear in academic works focused on the pipa arts. Women, moreover, hold an othered status within the discipline. This dissertation argues that the gendered associations of the pipa have reinforced a power structure that privileges men and excludes women from participation in the professional community by devaluing women's musicality and entertainmentizing their creative contributions. This study examines historical materials to uncover connections between the pipa and women in historical contexts. It focuses particularly on the often-overlooked context of Chinese courtesan culture as well as the role that courtesan culture played in the instrument's gendering. Furthermore, through field research, I analyze the artistic and life journeys of three generations of 20th and early 21st-centuries female pipa musicians. My personal perspective as a pipa musician and ethnomusicologist provides a first-hand account of how female pipa players interpret and construe gender identities and performances through music making.