Biography from Been publishing, I’m back
James Montgomery Flagg was an early master of pen and ink, but he was much more. Born in 1877, he grew up along with the reproduction technology that allowed artists to select the pen as the illustrative tool of choice. Charles Dana Gibson, who pioneered 
many of the techniques that Flagg would draw upon, was ten years older. Others born within a year of Flagg include Stanley M. Arthurs, Ivan Bilibin, Walter Appleton Clark, Fanny Y. Cory, Frank Leyendecker, Norman Price, Harry Rountree, Frank Schoonover, Everett Shinn, J. Allen St. John, Sarah Stilwell, and J. Scott Williams.
A true child prodigy, Flagg sold his first illustration, to the prestigious St. Nicholas Magazine no less, at the age of twelve. You can read about his early encounters with the editor in a 1915 article in The Century.
This early sale proved not to be a fluke. By the age of 15 he was on staff at both Life and Judge, the premier humour magazines of the day. Below left is an 1894 illustration from Life. Below right is an early drawing from Judge, probably circa 1905.
It’s kind of hard to imagine today, but the teenage Flagg grew up in the company of some of the most respected magazine editors of the day. Drawing was his passion and the traditional pastimes of youth were of no interest to him. Although he spent several years in art schools, most notably the Art Students League (1894-1898), his real education came from the material that passed over the desks of the editors of St. Nicholas, Judge and Life. These he was allowed to study and the lessons he learned from them were more valuable than all of his schooling. Those same publishers made use of the young Flagg for his earliest magazine covers are from 1895 and ’96.
From 1898-1900 Flagg studied painting in England and France. His first book was Yankee Girls Abroad (1900). That same year he had a portrait accepted to the Paris Salon, but he felt that painting was not his forte and returned to illustration. Above left is an image from the January 1902 issue of Harper’s Monthly – perhaps the only work he did for the magazine.
Most of the early years of the century were still spent at Judge and Life and Harper’s Weekly – Life released four collections of his "limericks" (just clever poems, really) in 1904. By 1905 he began to illustrate books again. At right is one of the plates from An Orchard Princess from that year. These early efforts were mainly paintings, despite his focus on pen & ink at the humour magazines. It wasn’t until about 1906 that his recognizable pen style appears in his book illustrations. A good example is show below from Simon the Jester (1909).
Flagg was a rakish fellow whose cocky self-assurance served him well in the highly competitive illustration markets. Stories abound of his deeds and misdeeds. Susan E. Meyer in her excellent James Montgomery Flagg relates how he persevered in his 
attempts to break into the Scribner’s Magazine market. He was finally, so the story goes, asked to tackle an assignment that had stumped three other artists. Flagg supposedly solved the problems of this difficult Voodoo storyline and became a regular contributor.
All well and good, except I’ve checked all the Scribner’s from 1904 through 1907, when he is an established contributor to the magazine, and there doesn’t seem to be any JMF Voodoo story. In fact, his first appearances in 1906 are rather pedestrian. But it makes a great story…
Flagg was outspoken and lived a bohemian style of life. Despite a marriage that lasted from 1899 until his wife’s death in 1923, he was known for his cavorting around town with pals like John Barrymore. He was close friends with many of his contemporaries: Arthur William Brown, Walter Appleton Clark, Ham Fisher, Rube Goldberg, etc. Flagg was a founder member of the infamous Dutch Treat Club in 1906 (its president in 1913), a loose association of creative types that turned into an organization still going strong today.
Retrorambling 