John Held, Jr. attended the University of Utah from 1907 to 1909, and while there illustrated the Utonian, the university yearbook. He was also sports' cartoonist for the Salt Lake Tribune. In 1910, with $4 in his pocket, John went to New York to make his fortune in commercial art. He initially designed streetcar posters, but quickly advanced to art work for Wanamaker's. He enlisted in the U.S. Navy during World War I. Then after the war, the artist continued his college studies at Princeton, where he was voted “'Favorite Artist.”' His best known cartoon character, “'the flapper,” began to evolve in drawings during those days.

By the end of 1920, a rather pudgy, single-eyed “cutie” had appeared in the pages of Judge. She went through several stages as she appeared in such publications as Judge, Life, and Collier's, and in a syndicated newspaper strip called Margie. Much of this work did not really surface until after his death.

For John Held, Jr., the crash of 1929 signaled not only “the demise of the flapper,” but the destruction of his personal fortune. Held went to Hollywood in the mid-30s, and hung out a shingle that read: “Open for screen-writing after 4 years of experience in Hollywood.” In that same year, he also spent time in Utah giving talks on personal aesthetics at the Art Barn and the Hotel Newhouse. While Held was in the state, a friend and fellow artist, Roscoe Grover, asked the New Yorker what his favorite color was. 'Plaid,' he answered.