John Armstrong was born in 1893 in Hastings. He studied at St. John’s College, Oxford, 1912-13, and then at St. John’s Wood School of Art 1913-14. During the war he served in the Royal Field Artillery 1914-19, before briefly returning to St. John’s Wood School. He began his professional career as a theatre designer in London, gaining important patrons including Lillian and Samuel Courtauld, who commissioned Armstrong to decorate a room in their Portman Square home. His first solo exhibition was at the Leicester Galleries in 1928. In 1933 he joined Unit One alongside Ben Nicholson, Paul Nash, Edward Burra, Henry Moore, Edward Wadsworth, John Bigge and Barbara Hepworth, with whom he exhibited at the Unit One exhibition. From the early 1930s onwards his work became Surrealist in style – uncanny, romantically dream-like and heavily imbued with symbolism. Armstrong died in 1973. His work is held in numerous international public collections including the Tate, the Imperial War Museum, the National Galleries of Scotland, and the National Gallery of Australia.

The first appearance of Harlequin, a stock clown figure from Italian commedia dell’arte of the sixteenth century, in Armstrong’s oeuvre was in 1941, when he painted himself as Harlequin. From this point onwards Harlequin and clowns became essential characters in Armstrong’s output, and were the protagonists of the battle series and related works. Following the famous literary tradition, the clown or fool in Armstrong’s politically tinged works represents the only good and truth-telling man in a world full of lies, evil, cowardly and foolish acts. In the introduction to the catalogue for his 1951 Lefevre show, Armstrong expanded on the figure of the clown, writing he is “the image of frustration, fighting battles of nothing, attempting a leap forward but doing a back-somersault instead…[assuming] other aspects of humanity in its predicament”. In this sense, Harlequin also becomes the Everyman, tossed in the turmoil of a chaotic world.

The Jockey is very closely linked to the earliest self-portrait Harlequin, 1941, and part of a small group of paintings in 1947 including Bust of Harlequin, Pierrot (another named commedia dell’arte character) and Puppet. These commedia dell’arte figures were frequently used in puppet shows, and evidently Armstrong plays with the connections between puppetry, theatre and folklore stories such as Pinocchio, whilst also foreshadowing the central scarecrow character of his monumental history painting, Victory, 1958; Royal Academy Collection [cat. 19]. The Jockey appears disconcertingly somewhere between human and toy with a wooden nose and glass eyes, wearing jockey silks with the recognisable lozenge patterning of Harlequin. The portrait bust format plays with the Dutch Golden Age genre of the tronie, generally depicting an unknown sitter in costume. With the suggestion of a ruff collar and puffed, ruched sleeves Armstrong paints The Jockey with tongue firmly in cheek. This select group of puppetry inspired busts are particularly uncanny, with the sitters suspended between animate and inanimate and tinged with shades of the underlying menace of many folklore tales, recalling the Surrealists’ fascination with the uncanny ‘living doll’ of the mannequin. The Jockey, as with Armstrong’s other harlequin paintings, is a deliberate continuation an international avant-garde tradition – not just of the Surrealists but also conscious of the legacy of Picasso’s Rose Period harlequins.