James Montgomery Flagg (1877–1960) was one of those rare naturally gifted artists who seemed to be practically born with a pencil or paintbrush as an appendage.
By the time he was 12 years old, he had sold his first illustration―not to a family member or friendly neighbor―but to Scribner’s St. Nicholas magazine. By the age of 14, he was regularly contributing illustrations to Life magazine. He was a staff member of Life magazine’s primary rival, Judge, at 16.
He was born about 10 miles northeast of Midtown Manhattan, created illustrations for various magazines, and soon perfected his craft by studying at the Art Students League of New York from 1894 to 1898, as well as art schools in London and Paris from 1898 to 1900. In 1904, he made his home in New York City, opening a freelance art studio. The demand for his work was consistent and lucrative….