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In this chapter, I consider two nearly forgotten artistic practices: that of British painter Thérèse Lessore and circus proprietor and manager John ‘Broncho Bill’ Swallow, whose circus Lessore painted on several occasions. Despite Lessore’s significant output and the positive critical attention her artwork received during her lifetime, her career has been overshadowed by that of her second husband, Walter Sickert. Both artists shared an interest in watching, drawing, and painting popular entertainments. Even before they were married, they frequently attended music halls, theatres, and circuses together to gain inspiration for their art. From 1927 to 1934, the couple became regular attendees at the annual World’s Fair circus in Islington, which Lessore captured in several paintings. Dating back to 1883, the World’s Fair, with its circus, animal menagerie, rides, and other novelties, brought the splendour of the summer fair into the Christmas period where it was sheltered from the winter elements by the Royal Agricultural Hall. From 1920 to 1938, the fair’s circus was overseen by John Swallow, a skilled acrobat and equestrian who had acquired his reputation in the circus industry with his famous Broncho Bill Circus and Wild West Show which toured Britain in the late 1910s and 1920s. ‘Swallow’s Circus’, as the Christmas circus under his directorship came to be known, was the highlight of the annual fair. It was Swallow’s Circus that the Sickerts sat down to draw in the winter of 1927, and in subsequent winters until 1934, their final year in Islington together. As well as offering a double resurrection of Lessore’s and Swallow’s careers, this chapter considers the ways in which Lessore and other women artists were critically excluded from modernist art discourses; and how, by attending to a subject that had historically been the domain of the male modernist – for example, the circus – Lessore appears to insert herself into a specific modernist lineage.