On 1 December 1783, Edmund Burke delivered an impassioned speech in the House of Commons, urging Parliament to reform the East India Company, which Burke argued was ruling Bengal with venality, cruelty, and corruption. If Parliament failed to act, Burke cautioned, not only would Britain’s Indian subjects suffer the consequences but so would Britain itself: “as English youth in India drink the intoxicating draught of authority and dominion before their heads are able to bear it . . . neither nature nor reason have any opportunity to exert themselves for remedy of the excesses of their premature power.” Burke’s fear that the imperial project was corrupting the moral pedagogy of young British men – “the boys we send to India” – illustrates the intricate links in the British imagination between empire and masculinity, a pairing that this dissertation explores in the context of eighteenth- and early nineteenth-century literature. As a range of writers with diverse social and political allegiances attempted to make sense of the unfolding imperial modernity, two questions appeared inseparable: what it meant to rule an increasingly vast, transoceanic empire and what it meant to become a man, specifically a gentleman. The enormous wealth sailing up the Thames from colonies abroad was radically transforming historical modes of gentlemanly authority, allowing boys and young men the alluring possibilities of radical self-transformation and social ascendancy as old paradigms of title and consanguinity slowly gave way to cunning, industry, and capital. Yet Burke’s warning to the Commons hints at a darker obverse to these enticing prospects – the idea of imperial man becoming not a virtuous, right-feeling gentleman of the settled Whig order but a capricious tyrant who threatened the very foundations of that order. Although I take as my object of inquiry the eighteenth-century gentleman – that allegedly hegemonic masculine typology – my work develops, as well as contests, recent accounts by critics such as Nancy Armstrong, Felicity Nussbaum, and Srinivas Aravamudan. These studies have greatly expanded our understanding of the central role of women, members of the non-propertied classes, and colonial subjects in the ideologies and historical-political struggles of the age. By renewing attention upon the British gentleman, I argue that even within the most idealized, authorized versions of masculine identity, the ambivalences and upheavals brought about by imperial modernity roil just below the surface. While Erin Mackie has compellingly written that the British gentleman of the latter half of the eighteenth century worked to revise “patriarchal power as paternalistic benevolence,” I demonstrate that producing a coherent account of authority in a beneficent modernity while perpetually referring backwards to premodern, absolutist patriarchy was a balancing act always already on the verge of collapse. The heroes of empire that my chapters explore do not succeed in assuaging the trauma and anxieties of the imperial world so much as they do in registering the weight of those tensions. The arc of the dissertation encompasses four masculine types, emblematic of the period, to assess how the interplay between representations of masculinity and imperial ideology transformed over the century. But I also assess striking commonalities that illuminate the evolving set of discourses these figures sought to reconcile. My first chapter treats Daniel Defoe’s Robinson Crusoe (1719), a novel generally understood as oriented emphatically around a Whig view of commerce and empire but riddled with Crusoe’s repeated assertions of absolutist patriarchalism (an ideology anathema to Defoe as a political writer). I focus on these frequently overlooked and easily dismissed moments to uncover the serious moral and ethical dilemmas colonialism raised even at this early period. This chapter argues that Defoe sets these assertions against the novel’s Whig and proto-capitalist ethos to suggest the creeping tyranny that could develop in young men abroad, laboring far from the civilizing constraints of British society. At one level, Defoe’s novel presents the colony as a potentially liberating location (for Europeans), where the man of industry and capital could rethink and rearticulate his social and political identity. However, Robinson Crusoe also presents the colony as a profound threat to classical-liberal modernity – a wild and ominous space where the Old World’s despotic political demons threaten to reemerge in European colonists. Masculinity in Defoe’s novel is thus a site of possibility and a lens through which to critique the drives and desires that made empire so alluring. The anxieties that grow out of this opposition are present throughout the texts my subsequent chapters take up, although the ways in which these anxieties manifest shift with changing historical circumstance and location. Chapter Two reads Tobias Smollett’s Roderick Random (1748) alongside Henry Fielding’s magnum opus, Tom Jones (1749), as it works toward a theory of how the eighteenth-century novel reenvisioned squirearchy. I contend that Smollett and Fielding both conceive gentlemanliness as a social performance and that, especially for Smollett, this performativity at once allows for a liberating self-fashioning and throws into question the nature of masculine agency itself. The two novels explore a moral and behavioral pedagogy that ostensibly enables the modern would-be gentleman to persuasively inhabit his social position and gain control over his economic destiny by mastering a gendered performance; but these novels are also subtended by a fear that gentlemanly authority so founded becomes show without substance. The retention and revision of a premodern, patriarchalist identity symbolized by the English squire or Scottish laird serves as a means of defending an upper-class masculinity conceived as traditional and more concretely agential even as the conceptual underpinnings of this patriarchalism are put under tremendous pressure. In Smollett, the telos of the gentleman ensconced in his country seat and removed from the sphere of imperial commerce reads as the reward for successful participation in the imperial project, which also promises to confer British-gentlemanly status on young men of the Celtic periphery. In Fielding, inheriting Squire Allworthy’s estate appears as the pledge of Tom’s learned virtue and demonstrated capacity for beneficent authority. However, both texts are dominated by the fear that this revised squirearchy will fail; the anxieties of modernity are soothed only by recourse to a patriarchalist figure dangerously proximate to tyrannical absolutism – and whose coherence in imperial modernity is highly suspect. Thus, this chapter treats the insufficiency of an historic symbol of gentlemanliness alongside the failure to fully conceive a stable, alternate possibility. The second half of my dissertation tracks how the concerns that troubled Burke interrupted efforts to put iconic gentlemanly identities to the work of empire. Chapter Three discusses James Grainger’s 1764 georgic, The Sugar-Cane, which follows the English squire to sea, recasting the Caribbean planter as of a type with historic modes of masculinity in a bid for cultural relevance and to establish command over an alien, hostile place. Taking up the deep imbrication of Whig ideologies of property with planter prerogative in Grainger’s poem, I argue that The Sugar-Cane attempts to produce an almost boundless authority out of Lockean property right. The micro-focus on the colonial estate seeks to yield a British dominion that could span the globe, rendering the Caribbean gentleman as a foundational figure for a newly imperial subjectivity that Grainger works to establish. However, colonial inscrutability, metropolitan misapprehension and derision, and the inescapable horror of transatlantic slavery press the planter-as-squire conceit to its conceptual breaking point. I then analyze Samuel Foote’s 1772 farce, The Nabob, which explores the deleterious consequences for Britain itself if one vision of corrupted power and agency were to supplant enervated forms of gentlemanliness. Foote’s text, I argue, reverses Grainger’s concepts of imperial authority, envisioning wealth produced in the colony as the means for projecting power from the periphery back toward the metropole with vitiating malevolence. Finally, Chapter Four assesses the role of the country gentleman in early nineteenth-century national tales and historical novels. I contend that Sir Walter Scott’s Rob Roy (1817), Maria Edgeworth’s The Absentee (1812), and Sydney Owenson’s The Wild Irish Girl (1806) all deploy reformulated patriarchs in ultimately ambivalent attempts to anchor their vision of Union. In these three texts, all of which work through the place of the near-colony in the burgeoning empire, the reiterated squire is at once a stabilizing force of reconciliation and benevolent governance and a figure of tyranny and caprice who is paradoxically teetering on the verge of obsolescence. Throughout, the dissertation explores a dialectic of the residual and the emergent within masculine typologies that fail to reconcile received mythologies with unfolding imperial realities. By exploring the instabilities inherent in supposedly dominant gentlemanly typologies, and the ways that those instabilities are registered and mediated in literature, I aim to complicate received accounts of the ideological turmoil at the heart of empire in the long eighteenth century and to produce a more complete understanding of this turmoil’s continued reverberations.