This chapter begins by exploring the problems of defining ‘literature’ and establishes the capacious and intrinsically interdisciplinary nature of its study. The body of the essay argues for the long-standing proximity of history and literature and the difficulties, and even undesirability, of disaggregating their underpinning skills and techniques. It focuses primarily on examples from the late sixteenth century: a period when ‘literature’ meant not ‘fiction’ or ‘creative writing’ but a more general ‘familiarity with letters or books’ and the ‘knowledge acquired from reading or studying them’ (OED), and a time when notions of both poetry and history were fluid. If the former skirts close to rhetoric (as in Philip Sidney’s Defence of Poesy (c.1582)), the latter frequently connotes ‘story’, rather sequence of ‘factual’ events, as in Thomas Lodge’s often fantastical ‘history’ of ‘Robert, second duke of Normandy’ (1591). Even when endeavouring to adhere to the historical record, early modern, humanistically-trained historians – following their classical forebears – adopt fictive techniques, especially prosopopoeia: a ‘figure […] that to stirre and moove affection, attributeth speech to dead men, or to wals & such like’. School-room exercises drilled sixteenth-century pupils in this practice of personation, teaching them to ventriloquise the dead. As the essay goes on to demonstrate, prosopopoeia is particular useful when giving voice to those ‘overskipped’ by history, as seen from its centrality to The Mirror for Magistrates (William Baldwin et al.; editions from 1559) – a work which reflects self-consciously on the partiality of the historical record – and its use (alongside other fictive devices) by twenty-first-century historians and biographers seeking to restore voices lost or marginalised for reasons of race, class, or gender. The final section of the essay looks at how texts are shaped by their historical context (and vice versa) and the challenges of reading texts historically.