Born in Brooklyn, Silverman attended the School of Music and Art in Manhattan, where he was classmates with Harvey Dinnerstein, and the Art Students League. He graduated from Columbia University with a BA in art history, and served in the United States Army in 1950–51. In 1956, he and Dinnerstein traveled to Montgomery, Alabama, where they made drawings of the Montgomery Bus Boycott. Silverman built a career as a figurative painter, art instructor, and portraitist for magazines including Time and The New Yorker. Silverman has had many solo shows including a major retrospective at the Butler Institute of American Art. His work is in the collections of many museums including the Brooklyn Museum, the Denver Art Museum, the Smithsonian Museum of American Art, and the Philadelphia Museum of Art.
