This article explores Annie Proulx’s representation of trailer homes and those who live in them as illustrating her description of life as “slippery.” It reads several of her short stories and one novel to examine the ways in which Proulx acknowledges and undermines the stereotypes of people who live in trailers, subverting readers’ expectations and asking them to question their assumptions that trailers and trailer parks are synonymous with social marginalization, violence, and licentious behavior. In her darkest texts, Proulx uses the trailer motif to critique the idea that a poor or even middle-class person can easily thrive and attain social mobility, the American ideal. She takes a deterministic view that slippery forces of socioeconomic gravity pull one downward against the forces of free will and perseverance needed to transcend one’s socioeconomic class. The trailer, a form of relatively cheap housing that is flimsy and easily damaged, is the perfect architectural trope to represent such slipperiness.