A slip of a boy with a halo of brown curly hair and an intense stare stands with one hand in the pocket of a brown pea-jacket, his scarf casually knotted to one side. He could be a 21st-century model or indie pop singer, but this is Bob Dylan in 1966, posing in a freezing Manhattan street for Jerry Schatzberg, who is shooting the cover of his new album, Blonde on Blonde.

The singer personally chose the blurry one over the mutedly colourful set and this exhibition of 60 portraits (1963-66) includes two previously unseen from the shoot: Dylan hunching into the camera with a mock-menacing stare, and emitting an inscrutable Mona Lisa smile. Earlier, in the studio, he rolled on the floor wrapped around a conga drum and Schatzberg shot him from an angle, as if man and drum were propelled into space; he was, of course — into the unknown universe of superstardom.

The blurriness was no problem for Schatzberg: while most images are breathtakingly pin-sharp black and whites, a small, intensely dark picture has a porthole of light illuminating just the halo of hair, and elsewhere he is blown up to the point of distortion and the negative, scratched with “Bob Dylan”, shines like neon.

All through the collection, Dylan is mostly effortlessly cool, his look predating the Mods with meticulous double-buttoned shirts and sleek suits. Hunched over papers in the studio, as he adds finishing touches to Highway 61 Revisited, he is oblivious to Schatzberg’s gaze, but my eye is also drawn to the silhouetted Chelsea boots in this perfect period piece — and frozen historic musical moment.

Dylan’s trust in Schatzberg shines through these sessions. Today, we know of the singer’s other life as a painter and can reinterpret his blowing smoke like a shaman over a small painting of a woman, or posing with a Michelangelo repro. Like the paintings, these images lend new perspective on the intense, beautiful young man who became a poetic mouthpiece for millions.
Until 28 January (020 7839 4942, www.proudgalleries.co.uk).