Little research is in place to qualitatively understand the underlying mechanisms of the academic gender achievement gap in rural high schools. This study explores the meaning men attribute to the gender achievement gap in a rural, predominantly white, low-income high school. in the Northeastern United States. Drawing upon a hegemonic masculinity framework, I analyze retrospective interview data from 14 recently graduated young men. I find these men unconcerned, even confident in the face of academically superior girls. This confidence does not automatically translate to advantage in the real world, as I find roughly half the blue-collar participants working minimum-wage jobs after high school with little room for upward mobility. I also find a much smaller subset of college-going men experiencing varying outcomes in pursuit of post-secondary education. Findings suggest boys' underachievement in high school provides temporary power and privilege through masculine dominance, but translate to less predictable economic outcomes in early adulthood. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]