Douglas Hamilton was born in Dublin, the son of a wig maker. He trained at the Dublin Society School of Drawing under Robert West. After leaving the academy, Hamilton set up his business as a portraitist, painting small, oval portraits in pastel – or crayon as it was known. His relocation to London by the early 1760s brought commissions from the royal family, and in 1779 he was sufficiently wealthy to move to Italy with his wife and daughter. During his time in Rome he started painting large-scale history scenes in oil, in the popular neoclassical style. After his return to Ireland in 1792 he was widely regarded as the best portraitist in Dublin and was never short of work. From 1804 onwards he painted few works, and after his death some of his late portraits were finished by his daughter.