Historically, male students have been known to score lower than their female counterparts in reading and writing on standardized measures of academic success. While scholars, teachers, and even policymakers have attempted to explain and mitigate this gender gap in reading and writing scores, male students have had little opportunity to offer their insight into the research. Moreover, there is limited research about the causes of the perceived gap in reading and writing scores, or the potential ways in which the high school English classroom could be reimagined to provide a solution. This qualitative multiple case study explored how the experiences outside of the classroom in the lives of high school male students enrolled in an alternative education program mediate their reading and writing in the high school English classroom. Furthermore, this study explored how high school male students enrolled in an alternative education program perceive pedagogical elements in the high school English classroom. In particular, this study focused on the experiences outside of school of three high school male students enrolled in an alternative education program. These stories were told through individual, narrative portraits composed by the researcher which were composed based on the analysis of data from two focus group sessions and two semi-structured one-on-one interviews. Findings from the study indicate that there is a need to expand the understanding of literacy skills, as well as how they are recognized, practiced, and assessed in the high school English classroom.