This thesis explores two twentieth century blues artists, Son House and Honeyboy Edwards, and the confessional and critical voices in their art and lives. House (b. 1902), grew up and became musically competent in the black Baptist church in the American south during a period after reconstruction but before civil rights. When House reached adulthood in the 1920s the blues was prohibited and denounced by the Baptist church. House wrote and recorded "Preachin' the Blues" in 1930 in order to work through his anxiety regarding church ordinances that branded blues music as sinful and evil. In this text, House confesses the reality of his desire for whiskey, many devoted women, and a heaven of his own. In describing his fantasies House effectively criticized and resisted church efforts to promote temperance, chastity, and collective homogeneity. Honeyboy Edwards (b. 1915) aims his critical gaze at other institutions and ideologies. For Honeyboy, the blues is both an outlet for confession and a means of resisting the interpellative call of sharecropping, prison, police, and the draft; all these institutions view black males as anonymous and exchangeable and seek to collect and co-opt black male individuality for laborious and deathly purposes. Honeyboy's autobiography contains overwhelming evidence of the limited options available to black men from the nineteen-twenties to the nineteen-sixties as well as the brutal nature of work farms and white-operated prisons. Honeyboy's blues allows him to avoid and subvert such systems and, by playing the blues, reassert and recast his own personhood and agency. His song, "Build Myself a Cave," challenges the call of Uncle Sam's World War II draft by depicting the life Honeyboy will be forced to give up: freedom of movement, drinking and partying, and his lover's affection. Though House and Honeyboy criticize different institutions and each bear different apprehensions, their ultimate goal is very much the same. The two artists use their blues to candidly express desire and fantasy--the way things ought to be--and both men reconfigure their own place and purpose in the world through the blues. In doing this work of reorientation, both men reveal a deep and emotive understanding of the realities and limitations of the institutions and ideologies at work in their lives.