Henry's paintings include depictions of striking landscapes, symbolic folk tales, Japanese themes and society portraits. Born in Ayrshire, he studied at the Glasgow School of Art and joined the circle of painters known as the Glasgow Boys. His friendship with Edward Atkinson Hornel led to some collaborative work and they were among the first British artists to visit Japan, traveling there together in 1893. On their return in 1895 Henry's compositions reflected the impact of this visit but he concentrated on the more lucrative painting of portraits and established a successful studio in London.
The Glasgow Boys were a loose group of young artists that represented the beginnings of modernism in Scottish painting. In the early 1880s, 'the boys’ were united by their disillusionment with traditional academic painting, with its strong focus on historical subjects and high levels of finish. Instead, they painted contemporary rural subjects, often working out of doors and painting directly onto the canvas.