The aim of my paper is to illustrate the effects of trauma, loneliness, sportsmanship and the crisis of masculine identity on the verge of adulthood through the comparison of two well-known literary works published in the 1950s, which are also stories of liberation and self-awareness. These narratives are strikingly similar in respect of their protagonists, themes and opinions of the newly emerging era of consumerism: one is The Catcher in the Rye by the reclusive American writer, Jerome David Salinger, and the other is “The Loneliness of the Long-Distance Runner,” a short story by the working-class British author, Alan Sillitoe. The greatest difference between the two teenage figures (besides their social background) is evoked by the titles: the prep school dropout Holden Caulfield aims to catch something, which implies a quick and sudden movement, starting from a relatively motionless position, while the borstal boy, Colin Smith, is running, which is a mechanical motion that usually takes a longer time and has a goal. In my essay, I wish to analyse these dissimilarities by foregrounding questions that are linked to all the issues a sensitive adolescent could be interested in and explore them through the two tropes, catching and running. For instance, the authority figures, Mr Spencer in the novel and the borstal’s governor in the short story, compare life to either team sports or sports that one plays with a partner or alone, in order to help the boys make sense of life either as a group activity or as an action one has to perform alone. I am going to explain how their relations to society are determined by the fact that Smith is a sportsman, constantly under control, while Holden does not really care about sports anymore. My paper is also going to investigate the construction of masculine identities in the social and cultural context in which these narratives appeared, aiming to offer a comparative analysis of the significance of individuality, (team) sports, and the oppressive systems of control in British and American societies in the 1950s.