James Montgomery Flagg, James Montgomery Flagg was born in New York City on 18th June, 1877. He had a difficult relationship with his parents. he later wrote: "Loyalty to family as such doesn't seem to me pertinent. Family isn't sacrosanct to me. To hell with the snobbery of inheritance."
Flagg was a talented artist and when he was twelve years old he sold his first illustration to St. Nicholas for $10. The Century Magazine later reported that the editor recalled: "There was something in those easy, unstudied lines that breathed ability and capacity so great that words of praise and encouragement seemed only a duty."
By the age of fourteen he was a member of staff of the humorous Life Magazine. His work was greatly admired by the industry and two years later he was working for Judge, the most popular magazine in this field. In 1893 Flagg went to the Art Students League. Although he made some very good friends at the art school, such as John Wolcott Adams and Walter Appleton Clark, he was disappointed about his development as an artist.
In 1897 he visited London with his friend, Richmond Kimbrough. He also attended the art school run by Hubert von Herkomer. He later recalled: "There are no art teachers. Art cannot be taught. Artists are born that way.
They educate themselves, or else they do not become educated... I happen to have been born an artist. Ask anyone who doesn't know. I wasted six years of my young life in art schools. As far as any benefit accruing to me from them - I was working on the outside all the time, anyway. Nothing but total disability or death could have stopped me. I had to be an artist - I was born that way... You can't breed an artist. You can only breed mediocrity."
Flagg's main artistic heroes during this period were Howard Pyle and John Singer Sargent. However, he disliked the artist when he met him: "Sargent was more English than the English; in fact, not to be too refined about it, his manner was snotty." This experience did not stop Flagg from admiring Sargent's artistic gifts."
On his return to the United States he married Nellie McCormick, a woman eleven years senior. Flagg pointed out in his autobiography: "Here was the beautiful woman who had turned down a number of rich suitors to marry a poor but promising artist who was madly in love with her.... Nellie was a St. Louis socialite and knew all the richest people in all the big cities; up to then a realm of society entirely beyond my knowledge. In the early days of our marriage when I was short of cash, she put her allowance at my disposal in an utterly generous and unselfish way."
