Shirreff was born in Haddington, the son of an East Lothian farmer. He entered the Trustees’ Academy in Edinburgh in 1802, at the time when John Graham was master. Graham introduced oil painting into the curriculum, and also initiated a scheme of premiums for the best historical paintings. In 1805, Shirreff won the top prize for his first major attempt at history painting using oil paint. The picture is now in the National Gallery of Scotland’s collection (NG 2255). Sadly, and aged only eighteen, Sherriff died of consumption before the prize was awarded. It was bestowed posthumously.