In The Lives of Cleopatra and Octavia, Fielding reclaims classical learning for practical purposes by making the life stories of characters from distant cultures applicable to her readers. The Cleopatra of Fielding’s text remains exotic, yet in her enslavement to passions, she presents basic human qualities that transcend geography, time and culture. As a member of the Roman aristocracy, Octavia makes choices that Fielding’s readers would never face, but those same readers can learn much from her unhappy marriage to Anthony. In presenting the stories of these infamous and renowned women, Fielding explores a form of biography distinct from the panegyrics, hagiographies and spiritual biographies that preceded it and anticipates the directions of later-eighteenth-century life writing. In its unflinching depiction of the Egyptian queen’s darkness, the Cleopatra narrative, for example, captures the gritty realism of Sir John Hawkins’s Life of Johnson. In fact, Boswell’s critique of Hawkins’s biography—that the work contains “a dark uncharitable cast, by which the most unfavorable construction is put upon almost every circumstance in the character and conduct” of the subject—fits Fielding’s work more accurately than it does his rival’s. 1 The depiction of Octavia, at once nuanced, irreducible and ultimately tragic, looks toward the later achievement of Oliver Goldsmith’s Life of Richard Nash, which, like Fielding’s work, includes substantial embellishments in service of an instructive theme. 2 Although the words merit, folly and greatness carry different connotations in the Nash biography than they do in the Octavia narrative, Goldsmith’s overarching theme—that Nash had “too much merit not to become remarkable, yet too much folly to arrive at greatness”—captures the essential humanity of Fielding’s Roman matron. 3