Born in San Diego, California, Freeman studied at the San Diego School of Fine Arts, and in 1928 at the Art Students League in New York City under John Sloan and Harry Wickey. Freeman spent most of his career depicting the everyday life of New York City in the 1930s and 1940s. A talented artist, Freeman was an author, illustrator, painter, and lithographer. He spent the last 20 years of his life in Santa Barbara, California.