In 1877, James Montgomery Flagg was born at Pelham Manor, New York. Flagg also known as J. Montgomery, he was an early master of pen and ink, but he was much more. He was an American artist and illustrator who gain reputation during the first part of the twentieth century. He worked in media ranging from fine art painting to cartooning but he is mostly known for his political posters. Flagg was married twice. His first wife was Nellie McCormack who survived till 24 years and ended when she died. Dorothy Wadman was his second wife and did not have any children. He had a complicated relationship with his parents. He was enthusiastic about drawing from his young age James Montgomery Flagg is generally regarded by art historians as an extraordinary talented child, because at the young age of twelve, he sold his first illustration to a well known magazine. From 1898-1900 he studied fine art in London and Paris with his friend, he believed that artists were born with talents, not trained, and counted his formal art training as a waste of time. After that he came back to the United States where he created countless illustrations for books, magazine covers, political and humorous cartoons, advertising, and spot drawings. After a few short years later, Flagg was already an employee of illustrator for two main humor magazines. Although he created some achievement early in his career as a painter, illustration was his true passion. His earliest books illustrations, such as Yankee Girls Abroad (1900) and An Orchard Princess (1905), were done in paint. He had started to illustrate with pen and ink in 1906, a distinction that he would be defined by in the years to come in works such as Simon the Jester (1909).