Hackstoun was from Scotland and trained as an architect in Glasgow before starting a career in music and opera. In 1878 however, he introduced himself to John Ruskin as an artist. After seeing Hackstoun’s work, Ruskin said that although there was ‘real gift’ in his painting, there was ‘no use whatever in your seeing me. Work from Turner’s early drawings for six months and you will know all I can tell you.’ Hackstoun carried out these orders, and copies by Hackstoun of Turner’s works can be found in the Ruskin Collection.
Ruskin later started to tutor Hackstoun personally, taking him London’s National Gallery and intending to send him to France and Switzerland to paint landscapes for the Guild. Despite commissioning works in northern France, Ruskin seems to have lost interest in Hackstoun a few years later, unkindly saying that he would never be more than an amateur. After this, Hackstoun returned to Scotland and painted landscapes in his local area of Perthshire, where his works take on a more colourful and slightly dreamlike style.