This chapter explores some of the ways in which masculinities are made and remade through the representation of films, for example in the fight film genre and what could be called 'boxing films'. It examines the ambivalences in cinematic representations and the contradictions boxing reproduce, all of which contribute to the development of theories which offer explanations of the enactment, representation and experience of masculinity in the context of accommodating disruptions and managing anxiety. The chapter traces some of the transformations that have taken place, notably since the 1940s and 1950s into the new cinematic age of the twenty-first century. Films engage with and reconstruct dreams, fears, aspirations and dramas that are woven into the routine of everyday life, none more so than in 'boxing films'. Boxing films, like so many in the mainstream of cinema, which is a medium that trades in fantasy, may also appear to represent hyperbole and excess.