James Montgomery Flagg in his studio

James Montgomery Flagg was an American Illustrator that was born in New York , 1877. Best known for his political posters, Flagg was a powerhouse of an illustrator that delved portrait painting, poster art, and illustration.

Flagg was phenomenal at a young age, showing great enthusiasm for drawing around this time. When Flagg turned 12, his illustrations were accepted into national magazines. When Flagg turned 14, he was making regular contributions to magazines such as Life magazine and Judge. From 1894-98 Flagg went to the “Art Students League Of New York”; an art school in New York City at the time.

Starting 1898-1900, Flagg studied fine art in London and Paris whereupon his return he started to produce illustrations for more books, magazine covers, political and humorous cartoons, advertising, and many others.


One of Montgomery Flagg’s best known works is undoubtedly the Uncle Sam recruitment poster that he did for World War I. The identity of Uncle Sam actually rose around the 1800’s but was really solidified with Montgomery’s versions of the established character.

Even after the Golden Age had passed, Flagg was still having success in his career, with many large magazine companies asking for his illustrations.

Montgomery Flagg’s most famous piece: The Uncle Sam Recruitment Poster for WWI
Your Forests – Your Fault – Your Loss.
Jack Dempsey & Jess Willard Boxing Match

Summary/Personal Insights

Story Illustration for “Collier’s” American Brands

Looking at Montgomery’s works is stunning and “inspirational”. I don’t quite like this term as from my personal experiences, the word “inspirational” carries a somewhat half-blinded meaning towards it, as if a person had nothing to say other than “inspirational”.

Montgomery Flagg’s works light up the artistic passion in my soul, telling and motivating me to get better at my craft. A powerhouse artist at the time and as time passes on, Montgomery Flagg’s works will most likely continue to be discussed heavily in the future to come.