Thomas Killigrew (1612–1683) was the son of the courtier Sir Robert Killigrew (1579/80–1633) and Mary Woodhouse. By 1632 he was a page of honour to Charles I and was painted twice by Van Dyck. In 1636 he married a maid of honour to Queen Henrietta Maria, Cecilia Crofts, who died in 1638. He married a second time in 1655 Charlotte van Hesse-Piershil. Killigrew supported the Royalist cause during the Civil War and went into exile after Charles I’s execution, during which time he went into the service of both James, Duke of York and Prince Charles, the future Charles II. Killigrew worked as a playwright and theatre manager with a company known as the King’s Men. His best-known work was The Parson’s Wedding (1637).

In Killigrew’s later years he was painted in two religious but nevertheless theatrical guises: in the 1670s he was depicted by an unidentified artist as a pilgrim of St James (British Museum, 1849,0315.70) and, at some point after 1680, Willem Wissing portrayed him as St Paul carrying the sword of his martyrdom (British Museum, P,6.38). The present oval portrait, signed by Wissing, appears to be a frank portrayal of the aged Killigrew, with a rather protruding lower lip, watery eyes, flat hair and an age spot on his cheekbone.

Another portrait of Sir Thomas Killigrew featured in the 1904 Raynham Heirlooms sale.¹ That portrait, purchased by Leggatt for £39 18s, and which depicted the sitter in ‘rich red dress, with breastplate and sash, white sleeves and lace collar, caressing the head of a dog’, was evidently a version of the much earlier portrait of Killigrew, c.1635, by Sir Anthony van Dyck, the original of which belongs to the Weston Park Foundation, Staffordshire.