Some art can be made in solitude, straight out of the artist’s head. But portraiture is a game for two. That’s the lesson of The Encounter: Drawings from Leonardo to Rembrandt, a marvellous little exhibition at the National Portrait Gallery. It is essentially a medley of Old Master works on papers from various British collections — which might sound a little on the quiet side. But that would be the wrong conclusion: on the contrary it poses intriguing questions and is full of visual pleasures.

‘Head of an Elderly Man
Wearing a Cap, probably Mino da Fiesole’ (c.1480–3) by Filippino Lippi
Notable in the latter category is a long row of Holbein’s studies of the early Tudor court and a striking array of works by Annibale Carracci and his school. But there is much else to pore over: these are often intimate works, which take you physically close to the marks of the artist’s hand. It’s worth peering to take in a tender little study by Filippino Lippi of a fellow artist, the sculptor Mino da Fiesole (c. 1480–3), or to examine a tiny Parmigianino profile of a little boy (c. 1535). But The Encounter also makes a serious point: any portrait is the record of a meeting between two people — which is why it is a complicated business.

‘Woman in a Netherlandish Headdress’ (c.1526-1528) by Hans Holbein the Younger
For one thing, a portrait may be affected not only by what the artist knows about art, but also by how well he or she knows the subject. One of the most touching in the show is Carlo Dolci’s red and black chalk study of his shoemaker (c. 1630). This tiny, careworn man with enormous ears is half smiling, as if chatting with the painter — as he probably was.

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