Throughout the nineteenth century, Seurat's fairground subject—known as the parade in French and loosely translated as the "come-on" or sideshow—was a stock motif in the popular press, enjoying widespread currency in caricature. It became an acute device for mocking politicians who, like saltimbanques, parade their talents on the road, giving stump speeches from one makeshift stage to the next with all the promotional flair of sideshow attractions geared to pull in the crowds.

The great caricaturist Honoré Daumier (1808–1879) recognized the versatility of the parade motif in a broad range of works that fully realize its expressive potential for pointed and poignant social commentary. Having long peppered the pages of comic journals with lithographic images that cast high-ranking officials as performers of low-brow entertainment, the seasoned illustrator turned to paintings and watercolors that vivify the marginal world of traveling players whose meager livelihood depends on the fickle whims of the public. Greatly admired by artists and writers of Seurat's generation for his economical draftsmanship, antibourgeois attitudes, and matchless verve, Daumier set a powerful precedent—not least in pioneering the composition of looking over and around the heads of fellow spectators to catch a glimpse of the show.

In Circus Sideshow, Seurat brought his long-standing interest in saltimbanques and his newly minted pointillist technique to bear on the parade, a subject that had been given memorable form by Daumier and a contemporary edge by popular illustrators. Made in the wake of the succès de scandale of his huge sunlit park scene, A Sunday on La Grande Jatte, Seurat's first painting of a nighttime urban entertainment is the most geometric and mysterious of the half-dozen major figure compositions that date to his short career.

Seurat depicts a well-publicized attraction at a time-honored event: the Corvi Circus troupe and its audience at the annual Gingerbread Fair held just after Easter in a working-class district of Paris around the place de la Nation. Yet descriptive detail succumbs to overall pictorial harmony in a painting imbued with the evocative power of his tenebrous drawings. The twenty-seven-year-old artist made cursory sketches in the spring of 1887 that identify the site, which was also divulged by a reviewer when the "nocturnal effect" debuted the following spring at the Salon des Indépendants.

Seurat's sustained fascination with the theme of the parade unfolds on this wall, which situates Circus Sideshow in relation to the conté crayon drawings that advanced his conception and the figure painting he developed and exhibited in tandem—a contrasting daytime, indoor studio scene. On the wall opposite, Seurat's choice of subject is amplified by the work of commercial illustrators and poster designers, whose efforts serve not only to contextualize Seurat's magisterial composition but also to clarify its elusive imagery.

Seurat chose a subject that attracted contemporary naturalist painters of like ambition who, in keeping with mainstream practice in the 1880s, sought official success at the annual Paris Salon with scenes from modern life that rang true to everyday social reality and would be readily understood by all. Placing a premium on faithfully observed detail and gravitating to conventions commonplace in popular illustration, they put their talents to the test of vividly describing the familiar spectacle: the lineup of performers on the stage; the jostling crowds representing a cross-section of society; and the sensory experience of vying to catch sight of the show—the lights, color, action—over and around the heady mix of fellow spectators. The broad appeal of the sideshow subject tallied with the egalitarian ideals of the era or, as one critic put it, the "democratic mania" that had infiltrated the Salon.

Enter Seurat, who distilled the pulse and flux of a time-bound event into a freeze-frame image of timeless allure.

As a painter and draftsman, Seurat increasingly focused his aloof and ironic gaze on scenes of urban entertainment in the last years of his career. He announced the new direction of his art, or staked his claim, at the 1888 Salon des Indépendants by showing Circus Sideshow in the company of four drawings of Montmartre music halls, or café-concerts, which likewise explore staged, gaslit performances—with striking results. Elegant in their stylization, chic in their simplified silhouettes of fashionable clothing, and concise in their articulation of the performers' gestures, they project a deadpan quality and an aura of silence at odds with the rowdy nature of the locales. Then at the height of their popularity, café-concerts, which offered a nightly fare of food and drink along with lively entertainment (though "never of a high class," a contemporary guidebook warned), had become as much a staple of Seurat's neighborhood as artists' ateliers. He identified the local haunts in his titles for the works. The quartet of drawings featured in concert with Circus Sideshow may be appreciated ensemble for the first time since 1888.

Seurat's interests were echoed by his Neo-Impressionist colleagues, who took up the same motifs for their own experiments in using the dotted touch, whether in friendly collaboration or spirited rivalry.

The studios of Montmartre in the late 1880s were full of artists in their twenties, not long out of school, keen to assert their independence and make their mark on the Paris art scene—but not necessarily with the Neo-Impressionist dot. Too novel to ignore, Seurat's style proved a rallying point for creativity, whether as a magnet or a target. Having risen quickly in the ranks of the avant-garde to assume a leadership role and a devoted following, Seurat was a force to be reckoned with as artists competed for prime spots—in new exhibition venues, upstart journals, and galleries on the lookout for fresh talent—and jockeyed for position with alternative picture-making strategies for rendering naturalism passé.

The general shift toward more suggestive and synthetic styles fostered similar experiments and subjects that dovetail Seurat's preoccupations in Circus Sideshow, from nocturnal effects to the evocative potential of low-brow entertainment. With the rise of socialism in France, imagery of itinerant circus performers, which conjured notions of marginality and alienation, gained ground among artists of leftist sympathies, alongside views of the gritty industrialized suburbs and the cabarets and brothels on the doorsteps of their Montmartre studios.

During the 1890s, the great era of the poster, the sideshow subject attracted a new wave of interest from a steady stream of artists eager to establish their reputations through success in the commercial world. The poster was modern printing technology's extension of the time-honored parade; both functioned to pull the public into the show.