This thesis argues that the representation of male thieves in eighteenth-century criminal life-writing is shaped by their relationship with objects, and shaped differently according to the nature of those objects. In spite of its formulaic, lowbrow and often uninspired characteristics, criminal literature proves in this respect a prime site for literary experimentation. Texts about criminals occupy a liminal space between high and low culture, a position mirrored by that of the criminals themselves and the objects they steal, as they circulate at the margins of legal society. The thieves' own hybridity is translated in the genres adopted by their biographers, ranging from poorly-written journalistic prose, more or less edifying sermons, to a plethora of literary forms such as plays or even epistolary fiction. The prevalence of objects as drivers of narrative affects every aspect of the criminal’s life, and invites investigation of matters of belonging, copyright, domesticity, gentility, and masculinity. Defined by their refusal, or inability, to conform with socially acceptable behaviours and occupation, thieves depend on their mastery of objects and the significations of those objects to succeed, whether in making a profit or evading arrest and execution. In accounts of thieves' lives, conversely, objects become animated and acquire a life of their own, dominating the narrative and representation, so that thieves themselves are in turn transformed into things, or manipulated into new functions. The thief’s relationship to objects varies in terms of both his own mobility and that of the objects he steals and fences. Hence, the thesis falls into two separate parts; the first considers London footpads and housebreakers, while the second is focused on highwaymen. While the London criminal circles might be seen as forming parallel dysfunctional underworld societies, highwaymen are more often treated as solitary itinerants at most in social relationship with an accomplice or a horse. I do not discuss female criminality except in so far as it plays a part in the biographies of the male felons examined here, as life-writing centred around criminal women focuses mostly on their illicit sexual practices rather than their relationship with the material world. An introductory chapter situates the analysis in relation to social, legal, and literary norms and conventions of the period as well as recent departures in critical thinking relevant to this thesis, such as thing theory and histories of material culture. Each subject chapter then investigates closely the distinctive and often carefully distinguished nature of an individual’s relationship with objects in the numerous publications that narrate his life. The first part of this thesis focuses on a London criminal underworld circle of the beginning of the century, each chapter dealing with one criminal figure in a group centred around the best known of them: Jonathan Wild. The first chapter is dedicated to footpad and housebreaker Joseph Blake, alias Blueskin (1700-1724), and his evolution from violent thug to picaresque figure. The next chapter follows escapist John Sheppard (1702-1724) and his struggle against material indicators of repressive legal power. The third chapter focuses on famed thief-taker and gang leader Jonathan Wild (1683-1725) and his peculiar position within eighteenth-century economic, criminal, and literary markets through his relationship with the material world. The second part of the thesis is centred on socially and geographically mobile highwaymen. It begins with a discussion of Dick Turpin (1705-1739) and his recreation and corruption of domestic structures. The next chapter is dedicated to James Maclaine, the Gentleman Highwayman (1724-1750), famed for his performative gentility, in which we observe character represented as possession. Finally, the last chapter focuses on John Rann, alias Sixteen-Strings Jack (ca1750-1774), and explores the representations of his sartorial choices in the context of popular gentility and masculinity.