Philip II (r. 1556-98) was Titian´s most important patron, and together they forged one of the most fruitful artistic relationships of the European Renaissance. Philip surpassed all of the Venetian painter´s previous patrons both in the number of commissions and in their variety. Unlike his father, Emperor Charles V (r. 1519-56), Philip was not satisfied with only portraits and devotional works; he also requested mythological scenes. The most important of Titian´s works in this genre were his poesie paintings, which constitute what may well be the most influential group of mythological paintings in Western art. They include Danaë (c.1553; Apsley House, London); Venus and Adonis (1554; Museo del Prado, P422); Perseus and Andromeda (c. 1554-56; Wallace Collection, London); Diana and Acteon (1556-59; National Gallery, London); Diana and Callisto (c.1556-59; National Gallery, London/National Galleries of Scotland, Edinburgh); and Europa (1559-62; Isabella Stewart Gardner Museum, Boston). Many of these works were openly erotic, which may come as a surprise because of the stereotypical image of Philip II as a champion of the Counter-Reformation, and therefore divorced from any sensual pleasures. Yet religious zeal and the appreciation of erotic art were not incompatible for Philip, especially from his youth through the crisis of 1568, the year that witnessed the start of the Eighty Years´ War between Spain and the Netherlands. In fact, at the time of his death Philip possessed the largest and finest group of erotic paintings in Europe, including outstanding works by Correggio and Titian. Philip kept these works at the Alcazar Palace, the royal family´s official residence in Madrid, and while we do not know their exact location therein, they must have hung on the ground floor, in rooms adjacent to the gardens, following the example set by Francis I of France (r. 1515-47) in the baths at his château in Fontainebleau

Titian and Philip II met on two separate occasions: in Milan in 1548-49 and Augsburg in 1550-51. During those years, Philip was still crown prince, and he posed for the artist in both instances. These meetings resulted in two portraits: the present three-quarter likeness that shows Philip wearing a rich, ermine-lined cape, his hand resting on a table and the other clutching a sword, and another, full-length depiction in which he wears armor. In contrast to the latter image, which celebrates Philip´s military prowess, this portrait evokes a subtle dignity and regal bearing. The Italian writer Pietro Aretino (1492-1556) celebrated the portrait in a sonnet, praising the prince´s profound gaze and majestic air. Titian executed both portraits for the prince himself, but the artist subsequently made replicas for family members and courtiers. These works constituted the basis for two other types of royal portraits: one in which Philip is seated (c. 1550-51; Cincinnati Art Museum) and the other, a full-length depiction in civilian clothing (c. 1554; Museo di Capodimonte, Naples; and c. 1554; Palazzo Pitti, Florence). The latter two works were not commissioned by Philip or by members of his family or court, but they must have been painted in response to the growing demand for images of the prince among leading Italian families, in this case, the Farneses and the Medici, respectively.

This portrait is usually identified with Titian´s first meeting with Philip in Milan. Titian painted a first (and now-lost) version for Philip as well as various replicas. The present work is likely one of the latter, and was probably commissioned by Mary of Hungary (1505-1558), Charles V´s sister and governor of the Netherlands. On November 13, 1553, Antoine Perrenot de Granvelle (1517-1586), minister of the Habsburgs in Brussels and bishop of Arras, wrote to Charles V´s ambassador to the English court, Simon Renard (1513-1573), to inform him that Mary was sending this portrait of Philip to his fiancée, Mary Tudor (1516-1558). In the letter, Granvelle warns that the portrait is not recent, and that it shows Philip with an inferior complexion than at present, as well as less mature and with a sparser beard. On November 19, Mary of Hungary wrote to Renard, explaining that the painting had been made three years earlier, and, while it had been considered a striking likeness at that time, it was now slightly damaged by age and by the trip from Augsburg. Mary closed with a suggestion that the portrait be contemplated with the proper light and distance, like all of Titian´s works (Text drawn from Falomir, M.: Splendor, Myth, and Vision. Nudes from the Prado, 2016, pp. 68-70).