The setting in Fiddling His Way is a rural New England kitchen, where members of a white family have paused in their work to listen to the music of an itinerant black fiddler. Viewers of the day would have recognized the black man as a former slave, making his way out of the South by means of his talent. In an era marked by political upheaval and often violent social change, the musician is portrayed as noble and self-composed. His rustic white audience welcomes him as an equal as they listen respectfully to his music.
Eastman Johnson was one of America's most sophisticated painters of everyday life. In the years around the Civil War, African-American life became one of Johnson's favorite subjects, and the Chrysler's painting is one of his most famous works in this vein. Among his strengths were his tender portrayals of children and his skill with complex, multi-figure compositions. Both of these strengths are revealed in Fiddling His Way.