This chapter discusses how the big-boy bedroom has been depicted in Hollywood cinema since 2000 and how adult men still living with their parents are portrayed. Developmental psychologists and rearing experts have long argued that the teenage bedroom is necessary for proper gender and sexual development, but in Western – and, particularly, North American culture – it is also considered a place that adolescent males need to leave behind lest they be considered immature or even a moral threat. These concerns have been echoed by contemporary pundits across the political spectrum. Drawing on a queer temporality perspective, I call into question normative assumptions pertaining to personal development by demonstrating how some life trajectories may be bent by diverging from the expected life course. Rather than seeing cinematic representations of grown-up men living with their parents as an expression of men’s juvenility, irresponsibility, or avoidance of long-term relationships, I argue that the pathologization of big boys in their bedrooms may be masking broader economic patterns that disadvantage young men and their opportunities for social mobility. Understanding the obscurantist nature of these bedroom anxieties helps us illuminate young men’s forgotten realities and their economic struggles in a neoliberal age.