This chapter focuses on Jerome K. Jerome and Israel Zangwill’s portrayals of urban men who carry out both voluntary and involuntary doublings and transformations, adopting different identities and having identities imposed upon them. The city of London is a space of particular transformations and disguises. These malleable selves engage with a crisis of national ideas of masculinity and manliness at the end of the century, where perceptions of class and gender in flux compete with the public image and stereotypes of urban, suburban, and low clerkish men. With these tropes New Humour is shown to be concerned with pretence and reality in society, discrepancies between social ideals and the way society actually is. New Humour’s men reject imposed identities and work to construct new modern ones.