Via a synthesizing analysis of representative Vaudeville Blues songs in relation to the affiliated advertisements posted by recording labels in a major black newspaper, the Chicago Defender, in the 1920s, this dissertation project seeks to illustrate how the image of “wild” black women is presented, or performed in an ambivalent but contested space created by contending social, political, economic and cultural forces in the race record industry. Constrained by racist and sexist gaze, such presentations and performances of “wild” black women still seize rare chances to invite conscious feminist interpretations, as their “wildness” voices out female independency, assertion and agency even in pain and sufferings. Under the influence of such “wild” imagery created by Vaudeville Blueswomen, Ma Rainey and Bessie Smith in particular, August Wilson, playwright, and Sherley Anne Williams, poet and novelist, both carry on the tradition of characterizing “wild women” but also diverge into two different destinations while engaging their individual artistic instincts in their works. Adapting five songs by the real Ma Rainey as the basis of characterization, Wilson remolds a “wild” “Ma Rainey” via his fictional incarnation in the play Ma Rainey’s Black Bottom (1982), who asserts her temporary and confined power in a sophisticated and shrewd fashion to defend her sexual subjectivity and musical integrity, within the boundaries of racist and sexist oppression and exploration in the recording industry. In contrast, Williams adapts the title, the theme, structure, language, idioms from Bessie Smith’s song “Any Woman’s Blues” and renders them interpretatively into her poem “Any Woman’s Blues,” to manifest the “wild” mindset of modern black women on the imperfections of relationship, such as loneliness, interwoven with senses of identity and belonging. The outstanding literary contributions of Wilson and Williams combining the Vaudeville Blues and literary works mark another vital endeavor of writing orature into literature. In this sense, this interdisciplinary synthesis would hopefully reinforce the necessity of researches on the intersection between music and literature which responds to the call of “a new tradition built on a synthesis of black oral traditions and Western literate form.”