Raphael was a precocious artist, developing a distinct and brilliant practice in his early years. 

But his Portrait of Baldassare Castiglione shows the indelible influence of Leonardo da Vinci, who influenced Raphael's work just after the turn of the sixteenth century. In only thirty-seven years of life, Raphael managed to influence entire generations of artists, writers, and leaders, including Henri Matisse.

Baldassare Castiglione was a courtier in early Renaissance Italy. A courtier was like the feudal equivalent of Smithers on "The Simpsons": no matter what, courtiers had to guess at the best thing to say that both preserved the illusion of independent thought and carefully stroked the ego of the boss. His 1528 Il Cortegiano, or "The Book of the Courtier," was very popular as a sort of "Pleasing Kings for Dummies," and it sold well for over a century, although eventually it began to serve as an emblem of the decadence and excess of monarchy which Nietzsche would satirize.

Castiglione was close friends with Raphael, whose portrait portrays the courtier presenting his most professional side, stylish enough to inspire his king, but not stylish enough to provoke jealousy. Then, as in today's apparently radically different society, artists needed to behave as courtiers themselves in order to maintain good relations with patrons, sponsors and other influential figures.  "The portrait of Baldassare Castiglione (1514-15) by Raphael projected images of unaffected self-confidence consonant with the main themes of "[The Book of] The Courtier"," i.e. the cultivation of sprezzatura, a studied nonchalance.  For both artist and courtier, the last gasps of the brittle feudal system required the most delicate balancing acts of humility and self-assuredness.

In 1519, the final year of Raphael's brief and effervescent life, Castiglione sat again for a portrait. Raphael may never have finished this painting. The artist was so engrossed in his work that when the ambassador of the Duke of Ferrara came to him on "urgent business," Raphael sent him away. There were extant, in 1908, three copies of a second portrait of Castiglione, which may have been finished by other artists from Raphael's lost original or his preparatory sketches, in which the courtier wears no cap, turning his head to the left, and which features "his armorial bearings and his name and deeds...inscribed in Latin on the panel."