Henry Holiday was a painter, illustrator, glassmaker, enamelist and sculptor. He showed an aptitude for artistic practice early on, studying at Leigh's Academy before being admitted to the Royal Academy in 1855 aged just 15. His figurative work is heavily influenced by the Pre-Raphaelites, particularly Edward Burne-Jones in whose studios he spent a large amount of time. Holiday’s most famous illustrations were produced for Lewis Carroll's The Hunting of the Snark and this collaboration with literature is further seen in this drawing.

In Characters from Shakespeare Holiday recontextualises some of the most familiar faces from literature, placing Shakespeare’s characters all in one setting. Lovers like Romeo and Juliet, Hamlet and Ophelia, and Titania and Bottom take up space in the centre whilst shadier characters like the three witches and Macbeth lurk behind them. The back of the drawing names each character.