Picasso is generally considered to have begun his Classical Period (aka Neoclassical; think Greco-Roman) in 1917, when he journeyed to Italy to design the set and costumes for Diaghilev’s Ballet Russe, and that is certainly when he began in full force. But three years earlier, during the height of his Cubist Period, while summering in Avignon, all the while creating many, many great Cubist works, he produced a handful of fully realized classical works. Except for the below painting, the most beautiful of them by far is this drawing, Head of a Man, with his surprisingly broken nose.
You may have seen, or seen illustrations of, the most famous of these first Classical pieces, the unfinished masterpiece (intentionally so, as most writers conjecture), L'artiste et son modèle (OPP.14:027, Musée Picasso, Paris), which interestingly remained unknown until after Picasso’s death:

To underscore the Classical nature of this work, John Richardson juxtaposes its illustration in A Life of Picasso right next to a photo of an Ingres, the great 19th Century Neoclassicist whose work influenced Picasso. That summer, Picasso also made a few drawings of the male subject of this painting, as well as four drawings of a ruggedly handsome man with a broken nose.
Picasso’s interest in men with broken noses first found artistic expression in 1903, with the small but wonderful bronze, Tête de Picador au Nez Cassé:

The picador seems sad, in that special Blue Period way. His misshapen nose is a metaphor for the human condition—all of life’s pain and suffering are concentrated in it. Yet this man bears his burdens proudly. His visage evinces world-weariness and resignation perhaps, but at the same time his upturned lip hints at a snarl, betraying his fighting spirit.
A few years later, there were four works entitled Le Boxeur or Les Boxeurs, beginning with a Blue Period watercolor and three cubist works of 1911-12 (although the painting among these three Cubist works bears no apparent resemblance to a boxer, as far as I can see). Although these are interesting works, none of them pack the emotional punch of the bronze.
When the broken nose next appears onstage in 1914, its bearer once again has a very expressive countenance, although stripped of all the Blue Period blues. He impresses us now with his sensitive eyes and mouth, and with his proud bearing.
Picasso was certainly capable of realism, as he did at age 12 or 13 with one of his earliest Classical works, a reproduction of a Greco-Roman statue (OPP.93:005, Musée Picasso, Paris) that you’ve probably seen illustrated before:

But he was never content to play it straight, at least not for long. At first glance, our Tête d’homme also looks fairly realistic, but upon closer inspection, as is so often the case with Picasso, the realism begins to break down. Bit by bit, the viewer begins to appreciate Picasso’s departures from reality: the rollercoaster lips, the bulbous cheeks, the wheat-like eyebrows, and, as usual, the asymmetric eyes and ears. And this one, which escaped me at first: the double philtrum (the vertical groove between the nose and mouth). Moving south, the left side of the neck and shoulders are what we’d expect to see, but on the right, with their misshapen contour and with the clavicles in between that much more resemble the wings of a bird in flight, Picasso has sacrificed naturalism in the service of anatomical invention. Yet all the component parts, realistic and not, fit together to form this wondrously graceful, stunningly beautiful portrait.
The striking work at hand is by far the best of the series, the only great one of the four. (See for yourself on the Online Picasso Project—the others are numbered OPP.14:112, OPP.14:113, and OPP.14:114. There is also the somewhat related OPP.14:142. While doing so, you could also convince yourself that his nose is actually broken, if indeed you don’t yet buy it.) This drawing is also the only one of the four that Picasso signed. In short, this is a highly important and exceedingly rare exemplar of the beginnings of Picasso’s Classical Period.