Works by Jerome K. Jerome, Barry Pain, Israel Zangwill and Robert Barr are shown to have representations of clerks, and similar figures, that express anxieties of clerkish enervation, but which also push back against these to imagine a valid urban masculinity in the face of more hegemonic versions. Jerome comically sends up the stereotype clerk in order to dismantle it, urban enervation is revealed to be a social construct. For Jerome, systems of work are a prison and self-definitions are found outside of it. Pain’s works show the underlying comedy in urban office work and finance, while his clerk negotiates preconceived ideas of masculinity and domesticity, ultimately making a case for an everyday manly heroism. Zangwill’s clerks have a fraught relationship with Empire and finance, they are simultaneously of national importance but also in danger of not fulfilling an expected heroism. Barr’s clerks thumb their noses at clerkish stereotypes, and the bureaucratic systems which constrain them. Work is to be escaped, in order to define themselves as men.