The dark tones and strongly modeled facial features of The Whistling Boy are characteristic of the Munich style that Currier learned at the Royal Academy.
Instruction at the Academy included the traditional emphasis on draftsmanship as well as exposure to the energetic style of the influential teacher Wilhelm Leibl. The Whistling Boy, completed soon after Currier left the Academy, balances these two emphases by using both free brushstrokes and a realistic approach.
Unlike most of the Americans to arrive in Munich in 1870, Currier stayed in Germany for many years. His painting influenced the Americans that arrived in 1880, who referred to him as the "old man" of the Academy.