Haile began to work in a surrealist style in 1936 while teaching part-time at the Hammersmith School of Art. Dream Carpenter is one of the artist's earliest known paintings in this manner; created before he became an official member of the British Surrealist group in 1937, and exhibited at the famous London Gallery in Cork Street, managed by Roland Penrose. The painting reflects the Surrealists' concern with the power of dreams and the unconscious mind. Haile was a lifelong insomniac, and would immerse himself in surreal painting sessions throughout the night, drawing upon somnambulant ideas and associations. The work bears resemblance to a watercolour by Haile entitled Woman Dreaming, 1940, in the collection of the Victoria & Albert Museum.

The often disturbing and violent imagery of Haile's work emerges from a consciousness profoundly disturbed by the spread of Fascism throughout Europe and the empires of the

Western capitalist states, whose overseas dominions had expanded after the First World War. And yet within such savagery there is - as Haile's friend, Charles Seward observed - a 'poetic sense of wonder and mystery, a sense of the revelation of 'deep-guarded secrets', which hint at least at the forces by which man can sustain his agonies and survive them'. He continued to write that the brilliant directness and economy of Haile's painting is nowhere better seen than in the oils executed between 1936-39: 'the execution is often of the greatest delicacy and elegance of line; the contour often beautiful'.