This introductory essay discusses central issues of European portraiture in the period of its decisive transformation in the later Middle Ages. Starting with the notion of an individual in the Middle Ages it moves on to consider means of pictorial representation of men in the High and later Middle Ages, and to reflect on portraits’ power to make an absent man present. All these issues are considered based on Central European examples, namely, portraits of Casimir the Great, the king of Poland; those of Charles IV, the holy roman emperor and king of Bohemia, and a celebrated portrait of Rudolph IV, the archduke of Austria, thus stressing their relevance to the development of early modern portraiture.