The format of the Renaissance (and later) portrait medal had its origins in Imperial Roman coins, which bore the image of the Emperor on the obverse (primary face) and a device or symbol on the reverse. The development of the commemorative medal as a type followed the spread and assimilation of Renaissance ideals and the revival of an interest in the classical world throughout European culture.

The history of this process began in Italy with Pisanello (died 1455), who trained as a painter and signed himself as such in Latin on the reverse of his medals. Over the following centuries many specialist sculptors were attracted to the art form. It was recognised that there was a ready market for medals among the growing class of collectors, usually members of the intelligensia or the gentry, who were attracted to small-scale works of art; in addition medals, especially official ones, were often made in large numbers for presentation. For example, the Gonzaga family of Mantua, great patrons of the arts, commissioned Leone Leoni - master of the imperial mint in Milan - to make a medal of Ippolita Gonzaga in the middle of the 16th century for just such an occasion. Ippolita was already famed for her beauty and accomplishments by the time she reached the age of 15, when Leoni cast this medal. She appears on the reverse as Diana, the huntress and moon goddess, and - as indicated by the presence of Pluto, Proserpina and Cerberus - as Hecate, goddess of the underworld. The medal format proved ideal for this type of personal and intimate object.