Sickert developed his famous composition of Ennui in a series of drawings, probably in late 1913 or early 1914, and made five related paintings of the subject. There followed three etchings of different sizes: small, medium and large. Ruth Bromberg also inferred the existence of an unfinished soft-ground etching of Ennui. All three finished etchings were made in or around 1915, but only the large plate was published at the time. It belongs to the series of Sickert’s etchings published by the Carfax Gallery. The medium plate was not published until 1929, but the unpublished proof states were most likely made in 1915 when Sickert first developed the plate. Ruth Bromberg recorded only two impressions from the fifth state of Ennui (The Medium Plate), and the other is owned by the Victoria & Albert Museum, London.

The models for Ennui were Sickert’s factotum, known only as ‘Hubby’ (he was presumably someone’s husband), and his charlady Marie Hayes. They were his domestic servants but also his accomplices. The scene is illuminated by artificial light and this casts a sharply defined shadow behind Hubby. The room in Ennui is identifiable as Wellington House Academy, and Robert Emmons stated that Ennui was painted there. Between 1910 and 1914, Sickert made many two-figure genre scenes in Camden Town that are among his best-known work, several of which—including Ennui and Jack Ashore—were studied from life in his room on the corner of Granby Street and the Hampstead Road. He referred to this address as Wellington House Academy after a school that operated from the premises in the early nineteenth century. Charles Dickens had been a day scholar there and based some of David Copperfield on his experiences at the school.