Art Young was born in Stephenson County, Illinois, on 14th January, 1866. His family moved to Monroe, Wisconsin, when he was a child to run a general store and a twenty-acre farm. When he was a boy Young borrowed a book from the local library that had been illustrated by Gustave Dore. Young was so impressed with these drawings that he decided to become an illustrator.
Young sent his drawings to journals in Chicago and at the age of seventeen had his first work accepted by the Judge Magazine. Soon after the publication of his first drawing, Young moved to the city where he studied at its Academy of Design. He paid for the course by illustrating news stories in the Chicago Evening Mail. Young soon developed a reputation as a talented artist and was offered work with the Chicago Daily News and the Chicago Inter-Ocean. In 1985 he married Elizabeth North and three years later they moved to New York City and Young became a student at the Arts Students League.
Young also had his cartoons published in Life and Puck and provided drawings to illustrate news stories for the Evening Journal. One of these assignments included a speech given by Keir Hardie, the British trade union leader and the first socialist member of the House of Commons. Later, Young recalled how listening to Hardie encouraged him to start questioning his previously held, conservative views.
In March 1902 Young was commissioned to draw an anti-immigration picture for Life. After it was published he sent back the $100 cheque and vowed that in future he would only draw pictures that reflected his own political beliefs. By this time Young's work was so highly valued that newspapers and magazines were willing to accept his drawings attacking inequality and supporting causes he believed in such as women's rights.
When Piet Vlag decided to start a new socialist magazine, The Masses, in 1910, he asked Young to join him. Other early members of the team included Louis Untermeyer and John Sloan. Organised like a co-operative, artists and writers who contributed to the journal shared in its management. According to Barbara Gelb: "After about a year and a half the Masses floundered and its tiny staff of contributors, which included the artist, John Sloan, the cartoonist, Art Young, and the poet, Louis Untermeyer, held an emergency session to rescue it. It was Young's idea to ask Max Eastman, a twenty-nine-year-old Columbia professor who had recently been dismissed for his radical views, to take over the editorship of the Masses."
In 1912 Max Eastman, a Marxist, agreed to become editor of the journal. In his first editorial, Eastman argued: "This magazine is owned and published cooperatively by its editors. It has no no dividends to pay, and nobody is trying to make money out of it. A revolutionary and not a reform magazine: a magazine with a sense of humour and no respect for the respectable: frank, arrogant, impertinent, searching for true causes: a magazine directed against rigidity and dogma wherever it is found: printing what is too naked or true for a money-making press: a magazine whose final policy is to do as it pleases and conciliate nobody, not even its readers."
Art Young later recalled: