Purpose: Much scholarly hand-wringing has concerned the academic engagement of Black and Latino boys. At the center of these conversations are questions of culture. Cultural disconnects between home and school are profound for students from marginalized communities, particularly so for young men. Prudence Carter asserts that young men in urban settings are more reluctant than their female peers to become "cultural straddlers"--students who adeptly navigate the cultural distance between school and urban communities. However, many Black and Latino boys succeed in school. This article will interrogate why some young men acquiesce to the cultural expectations of schooling, whereas others do not. Research Methods/Approach: Leveraging relational ethnographic methods, this article details the relationships, experiences, and masculine identities of two groups of young men--the Alpha Gentlemen fraternity and the Serpents of Steel Robotics team. Findings: This article argues that whether cultures of masculine play and toughness fit in academic settings depends on how masculinity is molded in relational contexts. Although dominant ideologies of masculinity--including play and competition--were significant in both groups, how the young men played and competed within their relational networks shaped identities that were more or less capable of straddling the cultures of home and school. Implications: The findings here elaborate Carter's framing of boys' cultural straddling, with implications for enhancing academic engagement among young Black and Latino men.