This research explores ways that masculinity is depicted in the HBO series The Wire, which aired for five seasons from 2002-2008. More specifically, I examine and analyze the character of Omar Little and his portrayals of hegemonic masculinities (HMs) and nonhegemonic masculinities (nonHMs) through a framework proposed by gender theorist James Messerschmidt. He calls for an unraveling of the concepts of HMs and nonHMs to aid in discovering which gender presentations accurately legitimate unequal patriarchal gender relations (2016). Omar Little transcends traditional notions of HMs based on his social location and provides insights about HMs and nonHMs that enhances clarity and understanding. An analysis of Omar’s gender presentation through the Messerschmidt framework offers young men and boys, and people in general, an opportunity to break away from the conventional ways in which masculinity is depicted and perceived in society. As an alternative to the traditional views of manhood that provide a standard to which young men and boys may feel compelled to fulfill, such representations of HMs and nonHMs in The Wire challenge the status quo and convey less oppressive and less violent ways of being a man.