World War II interrupted his studies, and McCloskey served in the Army from 1942 to 1945. Although he was struggling financially, he won the Prix de Rome in 1939 to further his art education in Italy. He worked steadily at his paintings, but sold hardly any. After graduation, he found jobs as a muralist in Boston and at home in Hamilton. He spent summers taking art classes in Provincetown, Mass. McCloskey finished art school in Boston and moved to New York City, where he entered the National Academy of Design in 1936. “After that, I tackled everything I could in drawing and painting, thinking I might become an illustrator of children’s books some day,” he told the Bangor Daily News in July 1996.
His prize was a scholarship to Boston’s Vesper George School of Art in 1932.
In his senior year, he won an art contest sponsored by Scholastic, the magazine for young students. McCloskey discovered his love for art when he took up printmaking, engraving and woodcutting in high school in his hometown of Hamilton, Ohio.
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