Fray Antonio de Guevara (1482-1545), the most prolific writer of pseudo-historical prose in sixteenth-century Spain, was named official chronicler by Emperor Charles V in 1526. Despite his title, Guevara never wrote a conventional history. A master of fictional semblance, Guevara self-fashioned his own literary personae or masks – among them those of friar, bishop, chronicler, courtier, imperial counselor, and court buffoon. In his pseudo-historical prose, Guevara resoundingly uses the voices of both the novelist and the court buffoon, entertaining the reader with humor, wit, satire, and irony. Artistically manipulating both classical and contemporary history, Guevara innovatively creates a vast and labyrinthine web in which history and fiction form an inseparable hybrid: a pseudo-historical narrative that heralds the essay and the modern novel.