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The struggles with masculinity by male characters in following August Wilson’s plays; Jitney, Fences, Joe Turner Come and Gone This paper will examine the male characters in the following August Wilson’s plays; Jitney, Fences, Joe Turner Come and Gone and their struggles with masculinity. There’s is a silent scream among the male characters to prove their masculinity. The male characters in each of these plays are fighting to prove their worth while trying to escape from someone or something. Each male character cry out for their sense of dignity and will fight to death to get it. August Wilson’s plays; Jitney, Fences and Joe Turner Come and Gone represent characters struggling with masculinity. Most of the male characters in these plays are attempting all means to prove their masculinity. They try to prove their worth either through avoidance of the expected responsibilities, or by running away from other people or things. This paper shows how male characters struggle with masculinity in August Wilson’s plays namely: Jitney, Fences and Joe Turner Come and Gone Wilson shows the African-America’s struggle at different times since the abolition of slavery in America. Whereas male characters in Joe Turner Come and Go fight for identity and authority as per the African believes, Troy in Fences is fighting a losing war by trying to protect his family against what he believes to be injustice. The place of women in the society also causes confusion as most women aren’t ready to be subjected to patriarchal slavery experienced during their days as slaves. Men on the other hand are struggling to be the main providers and family protectors, despite the hardships in securing well-paying jobs or other opportunities. It their attempt to show their masculinity, most of the male characters fail terribly. How have African American men defined their masculinity? Assimilation to or separation from hegemonic masculinity is the first question that appears to attract August