A bust length portrait of a man, facing front, bald on top, with a wing collar and tie.

The author Henry James (1843-1916) was born in New York, visiting Europe several times in his early life, and after studying briefly as a painter he contributed pieces of art criticism to American periodicals. In 1876 James settled in London, and on a trip to Paris in 1884 he befriended his compatriot, the portraitist John Singer Sargent. Two years later James persuaded Sargent to move to London, and thereafter wrote about his art repeatedly, most notably in Picture and Text (1893). By then Sargent was in great demand by British and especially American high-society sitters, but towards the end of his career he drew back from his lucrative portraiture practice, concentrating instead on murals and landscapes, and preferring charcoal to oil paint for his portraits.

Sargent had first drawn James in 1885, but he considered the portrait a failure and destroyed it; the following year he tried again, with more success, and the portrait was later reproduced in the literary journal The Yellow Book. In 1911 the author Edith Wharton (1862-1937) commissioned Sargent to execute another drawn portrait of James, and he sat to Sargent three times between 1 February and 14 March 1912. The first two sittings did not go well, and before the third James wrote to Wharton that ‘I have a certain amount of impression that he may sacrifice the work of the two other sittings and make a fresh start’. But on 16 March he wrote again to tell Wharton:

‘I have sat again to Sargent with complete success, and he has made an admirable drawing. He kept on with the work of the two previous séances - and brought it round, beautifully developed, and redeemed and completed. It’s a regular first class living, resembling, enduring thing. Now he wants to know if: first he has your leave to have it, for safety, photographed, in one or two copies. Second if he shall then send it to you to Paris - or if it shall await here - in his hands - your next possible, and it is hoped probable, coming ... P.S. He will have the thing at any [rate] glazed and framed - so as to guard against the rubs of the charcoal, etc.’.

Despite James’s approval, it appears that both artist and patron were unhappy with the portrait. Puzzlingly, Sargent wrote to Wharton on 28 March 1912: ‘The photograph that has reached me proves that I am right in considering H.J. drawing a failure - I will try again if his patience holds out - at any rate I consider your commission unfulfilled’. It is hard to imagine how a photograph can have persuaded Sargent that his own drawing was a ‘failure’; but for whatever reason the drawing remained with the artist. James was naturalised as a British subject in 1915, having been classified as an ‘alien’ and thus subject to restrictions on his movements on the outbreak of war. He was appointed to the Order of Merit at the beginning of 1916, shortly before his death, upon which Sargent presented the portrait to King George V.

Signed and dated below John S. Sargent 1912

Text adapted from Holbein to Hockney: Drawings from the Royal Collection