Studies on History, and specifically the History of Education, can take on different outlines, colours, hues (as Jacques Le Goff would tell us). It can, breaking with the usual "what", present itself from other paths, in walks that sound different, while also inviting. That's what this book is: a distinctive historical dialogue about Brazilian education at the beginning of the 20th century; in this case, that confined to the Imperial Pedro II College in Rio de Janeiro, under the avid gaze of the memorialist judge Pedro Nava. By analysing the intrinsic and extrinsic aspects of his production, we seek to discuss-produce a kind of cross-border historiography: one in which borders, without such fixed limits, set the tone. History, Literature and Education, together, tell of a time, a way of educating, a school culture in a certain space, in those times that formed the ruling male elite. It is therefore a question of delving into the nuances of the History of Education of a time-spaceand, from there, recognising the specificities as well as the similarities of the reality that operated there and of this time that is ours.