Bareback Rider belongs to Walt Kuhn's most significant body of work—his depictions of circus and theater performers. This series not only showcases Kuhn's commitment to modernist painting techniques but also reflects his deep fascination with the New York theater scene. Kuhn is well-known for his portrayals of female stage performers, often painted in the intimate setting of his studio. While capturing his subjects in full costume and makeup, Kuhn strips away the theatrical glamour and stage context, revealing a more profound psychological portrait of his sitters.

Bareback Rider epitomizes Kuhn's style and subject matter. The female performer stands in a confident pose, directly engaging the viewer—an indication of the skills she must possess as an acrobat, mastering daring maneuvers on the backs of moving horses. Despite her powerful stance, outside of her glamorous circus context, her expression is one of disillusionment, perhaps reflecting Kuhn's empathy for his subject, having worked as a theater director and costume designer in the early 1920s, where he gained firsthand understanding of the physical and emotional demands of the profession.

Kuhn, a Brooklyn-born artist, traveled to Europe in 1901 to receive formal art training in Paris and Munich, drawing inspiration from modern masters like Paul Cézanne. Upon returning to New York, his work as an illustrator brought him into the circle of progressive Ashcan School artists, including Robert Henri. Kuhn's unvarnished depictions of urban popular culture paralleled their work. He became a founding member of the Association of American Painters and Sculptors (AAPS) alongside Arthur B. Davies. This group would go on to organize the influential Armory Show of 1913, credited with introducing European modernist forms, such as Cubism, Fauvism, and Expressionism, to the American public. 

Kuhn's portraits of female circus and theater performers are widely recognized as an important moment within the history of American modernism. Other notable examples of his work are held in the collections of The Metropolitan Museum of Art, New York, The Brooklyn Museum, New York, The Crystal Bridges Museum of American Art, Bentonville, Arkansas, and The Phillips Collection, Washington, D.C., among others.