Hamilton, Hugh Douglas (1740–1808), portrait- and subject-painter, was son of a Dublin wig-maker. He entered the Dublin Society School of Drawing about 1750 and was a pupil there for some eight years, studying under Robert West (qv) and James Mannin (qv), and winning three premiums for the best drawings of 1756. In that year he was a fellow student of the future dramatist John O'Keeffe (qv), who later wrote that Hamilton ‘was remarkable for choosing, when drawing the human figure, the most foreshortened view, consequently the most difficult’. Hamilton probably left West's academy in the late 1750s, and soon set up a flourishing business as a portraitist in pastels. By the early 1760s he had moved to London, and in 1764 was awarded a premium by the Society of Arts for a now lost oil of ‘Priam and Hercules lamenting over the corpse of Hector’.
Portraits continued to be his main activity, and he exhibited them at the Society of Artists throughout the 1770s. In the early 1780s, economic security allowed him to move with his wife Mary and his daughter Harriott to Italy, where he stayed for about ten years. Hamilton lived mainly in Rome but also spent time in Florence (1783–5), Venice (1784), and Naples (1788). He painted an extensive number of pastel portraits, in both oval and rectangular frames, of British and Irish grand-tourists, including resident émigrés such as Prince Charles Edward Stuart and his family (1785–8; examples in the National Portrait Gallery, London, and Scottish National Portrait Gallery, Edinburgh) and long-term residents such as Frederick Hervey (qv), 4th earl of Bristol and bishop of Derry (c.1786; National Trust, Ickworth House, Suffolk). While in Rome, Hamilton developed a close friendship with fellow artists such as John Flaxman and especially Antonio Canova, solidifying his relationship with the latter by including him in a superb large-scale pastel (1788–9; Victoria and Albert Museum, London) where he stands with another artist, the Irishman Henry Tresham (qv), next to the early model of Canova's celebrated ‘Cupid and Psyche’ now in the Musée du Louvre.
A few years earlier, Hamilton made one of his first known attempts at a large-scale subject picture in oils, ‘Diana and Endymion’ (1783; private collection). Strongly influenced by the then current neo-classical style, this painting has much in common with the derivative antiquity that permeates Roman painting of the 1780s. At the same time Hamilton was purchasing a representative collection of old-master prints and pictures. Part of this collection was sold by Christie's in 1811. One item, the first volumes of L'antichita d'Ercolano (a lavish collection of fine engravings illustrating the discoveries made during the excavations around Naples earlier in the century) greatly influenced Hamilton's few attempts at historical oil paintings during these years. These influences found their most considered exposure in the oil painting ‘Cupid and Psyche in the nuptial bower’ (1792–3; NGI). During his thirteen years in Italy, Hamilton was successful and sociable; yet he stayed clear of factions, and his fellow Irishman, the sculptor Christopher Hewetson (qv), affirmed in a letter of 1792: ‘[he] belongs to no party yet [has his] share of business’. Hamilton also penetrated the Italian establishment, being elected to the Accademia del Disegno in Florence (1784) and painting a pastel self-portrait for Maria Louisa Bourbon, queen regent of Tuscany, who in 1805 bequeathed it to the Uffizi gallery, where it now hangs on the Corridorio Vesariano.
Hamilton returned to Ireland in 1792. While in Italy he had received commissions from a number of Irish grand-tourists, and he now renewed his acquaintance with such prominent families as the wealthy bankers, La Touche. Hamilton produced a series of pastel portraits for their various homes in Wicklow and Dublin. Similar commissions followed for William Robert Fitzgerald (qv), second duke of Leinster, Ireland's premier peer, at Carton, Co. Kildare. Hamilton had been reluctant to leave Italy, but political events made it a sensible decision. His regret on leaving Rome and his many friends are articulated in a number of letters written to Canova between 1794 and 1802, which inform us of the artist's activities and of the artistic stagnation and unenlightened patronage to be found in Dublin at the turn of the eighteenth century.
Yet Hamilton was never short of work. He complained to Canova of the large number of portraits that he had to complete, most of which were now in the more time-consuming medium of oils. He was by far the best portraitist in Dublin in the 1790s, and received the best commissions. In 1797 William Drennan (qv), a radical as well as a poet and physician, visited Hamilton's studio and commented on the range of portraits being produced – a large canvas of the charity preacher Walter Blake Kirwan (qv), as well as various portraits of the liberal peer Lord Moira (qv), and portraits of the United Irishmen Lord Edward Fitzgerald (qv) and Arthur O'Connor (qv). Between 1800 and 1804 Hamilton exhibited in Dublin with great success at the Society of Artists of Ireland exhibitions. He painted little during the last four years of his life, concentrating his time on a newly developed interest in science. His daughter Harriott finished off some of her father's late portraits. He died 10 February 1808 in his home on Lower Mount St., Dublin.