Stories of homelessness, both fictional and non-fiction ones, tend to occlude the factors that cause a loss of housing. From the time the term “homeless” first came to denote a person’s lack of long-term private housing in the late nineteenth century until today, what makes people unhoused has been and continues to be ignored, oversimplified, glamorized, or otherwise misrepresented. Whether it be novels, life writing, television, film, comic books, or journalism, cultural representations of unhoused lives predominantly center around a white, cis-male protagonist. Unlike most unhoused women and unhoused queer characters, the homeless cis-het white man may be placed in the role of hero, an admirable individual who overcomes hardship or who personifies a critique of the societal shortcomings of his time. This type of homeless hero thus serves to invisibilize the black and brown majority of unhoused persons in the U.S. as well as the large group of gender-queer folx and womxn among the homeless. My study traces the origins of this one-sidedness in stories of homelessness while also looking at some of the exceptions. My question is, firstly, how does the typical unhoused hero make us ignore the structural causes and realities of homelessness? And, secondly, how do those texts that bring a different perspective—different from the heroized cis-het white guy, that is—negotiate the relational and structural entanglements of poverty and marginalization?