While Norman Rockwell (1894–1978) painted rural America, James Montgomery Flagg (1877–1960) focused on the urban ideals. Born in 1877, Flagg was a child prodigy (child having extraordinary talent) whose talent saw him earning a steady income as an artist in all the popular magazines of the day by the time he was a teenager. Flagg was outspoken and lived a decidedly bohemian (not living by conventional values) lifestyle. His healthy ego served him well in the highly competitive illustration markets of the day.

Flagg's work featured many of his favorite models. His wife, Nellie, appeared in numerous illustrations, but the majority of his models were professional. They became known as "Flagg girls," and they were highlighted in books and posters, as well as every major magazine published at the time. These women always reflected the artist's view of the ideal woman rather than any current fad regarding...