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Illustration from Compton Mackenzie's Kensington Rhymes, 1912

John Robert "Jack" Monsell was born on 15 August 1877 at Cahirciveen, County Kerry, Ireland, the son of William Thomas Monsell, the Resident Magistrate. He grew up in County Limerick, spending much of his childhood at the home of his great uncles, the poet Sir Aubrey de Vere and the politician and scholar Sir Stephen de Vere, and was educated at St. Columba's College, Rathfarnham, Dublin. In 1902 the family moved to Chelsea, and Jack initially pursued a career on the stage.

His sister, Elinor May Monsell, won a scholarship to the Slade School of Art in London and became a painter, printmaker and illustrator, but Jack had no formal art training. Despite this, he became an illustrator, beginning with The Pink Knight, a story he had written, and illustrated in his notebook, to tell to a group of children. The publication of the book led to further titles such as Funny Foreigners, The Jingle Book, and Notable Notions all in 1905.

He contributed to magazines like the London Magazine and Little Folks while also working in comics, drawing "Dolly Dimple" (1904) and "Fido and Young Reggie" (1905) for The Monthly Playbox and many of his sketches appeared in Arthur Mee's Children's Encyclopedia.

During the First World War he served as an officer in the British Army, and suffered shell shock. He married the novelist Margaret Irwin in 1927, and went on to illustrate some of her historical novels. He also wrote librettos and designed sets and costumes for light operas, including an adaptation of Sheridan's The Rivals, which was performed in London. He died in Battle, Sussex, on 20 March 1952.