London-born artist Henry Singleton was brought up by his uncle, the miniature painter William Singleton. Henry attended the Royal Academy Schools from 1783 and started working as a professional portraitist at the age of sixteen. He exhibited some 285 works at the Royal Academy from 1784 until his death, but failed to become an associate of that institution. During his early career Singleton painted a number of remarkable history and genre paintings, many of which were widely distributed as engravings in mezzotint. Despite their success it was portraiture that earned him a living, with sitters including Lord Nelson, Lord Howe and James Boswell. In 1807 Singleton married his cousin – William’s daughter – who was a miniature painter known only as ‘Mrs Singleton’.