His mother saw that he was interested in art early on, and she enrolled him in the Columbian Council School, which later became known as the Irene Kaufmann Settlement.
Samuel Rosenberg spent one year at the National Academy of Design in New York, and then he came back to live in Pittsburgh.
During 1930s, Rosenberg's paintings were portraying the happiness and difficulties of life of the black and Jewish neighborhoods in the Hill District.
[3] Samuel Rosenberg painted for almost six decades in the twentieth century, during the Great Depression, and 2 World Wars.
Some of his students were Mel Bochner, Philip Pearlstein, Andy Warhol, Lois Katz Blaufeld, Rochelle Blumenfeld, Aaronel deRoy Gruber, Jane Haskell, Virginia Holzman, Anita Freund Morganstern and Abe Weiner.
His work was included in renowned exhibits, such as San Francisco's Golden Gate Exposition and 1939 New York World's Fair, and his paintings were selected by the Whitney Museum of American Art for inclusion in their early biennials.
In 2003 the Westmoreland Museum of American Art organized the exhibition Samuel Rosenberg: Portrait of a Painter with accompanying catalog of the same name.
[14] Samuel Rosenberg met his future wife, Libbie Levin (1898–1987) in the Hill District Library.