Painter, printmaker, and illustrator Howard Jacob Simon was born on July 22, 1902, in New York City. Simon showed an early interest in art and would frequent the National Academy of Design as a child and teen. While still in high school he attended classes at the New York Academy of Arts and worked as an illustrator for newspapers, earning enough money to travel to Paris by age seventeen. There, he studied for three years at the Acacemie Julian, primarily under Jacques Alexander, and took lessons in woodcut techniques from Japanese artists. He began establishing a career as an artist with a focus on social realism and landscapes. In 1926 he married fellow Academie artist Charlie May Hogue, a sculptor and children's book author who was born in Arkansas, and two years later they returned to the U.S., settling in San Francisco.

By 1930 the couple had relocated to Arkansas near Charlie's hometown of Monticello, building a log cabin in an attempt to live off the land while also maintaining their respective careers. As the Depression gripped the nation, the two focused on bartering their art for goods and services, and Simon divided his time between the cabin and New York, where he was on the faculty of New York University. In Arkansas he focused primarily on woodcuts and illustrations, and among the books he was commissioned to illustrate were La Rive Gauche, History of California Pathfinders, Candide, and more. He participated in shows in New York, San Francisco, and London. By 1936, however, Simon became disillusioned with homestead life and he and Charlie divorced, though they would remain artistic collaborators for many years, with Simon illustrating several of Charlie's books.

Howard Simon lived for a time in Paris, creating a series of etchings and paintings of the Bohemian crowd that he socialized with during his time there. In 1942 he wrote and illustrated 500 Years of Art in Illustration, published by World Publishing Company, and in 1970 he published Cabin on a Ridge, detailing his time in Arkansas and the people he met while homesteading. In 1971 he joined the faculty of the Barlow School in Amenia, New York, where he remained until his death on October 15, 1979. 

Simon exhibited with the California Society of Etchers, the San Francisco Art Association, and the Oakland Art League. He also exhibited at the Stanford Art Center (1928) and Paul Elder Gallery in San Francisco (1928, 1939). His work is held in the collection of Mills College (Oakland, CA), Grammercy Park Hotel (NYC), Baltimore Museum (MD), the New York Public Library, and more.