This paper presents a case for reading sport films like The Loneliness of the Long Distance Runner (1961) within an intertextual framework. To that end, Tony Richardson’s classic film is read alongside Paul Willis’ equally classic cultural studies text Learning to Labor (1977). Both reflect critical responses to a particular historical and cultural moment in post-World War II Great Britain. For deeper insight into the character of Colin Smith, these texts are also read next to the Alan Sillitoe (1959) novella on which the film is based. The compelling focus of each is on acts of resistance, yet in the end, each recounts an ironic tale of the reproductive power of rebellion. Taken together they explore in different ways the troubling suggestion that, satisfying as these acts might be, they can operate as a form of entrapment.