Born in Râmnicu Sarat, Romania, Steinberg began his career studying philosophy at the University of Bucharest but opted not to finish his degree, instead enrolling as an architecture student at the Politecnico di Milano in Milan. Steinberg fled Italy in 1941 with the rise of the anti- Semitic policies, eventually settling in the United States. He went on
to become one of the most recognizable illustrators of his generation, creating over 1,200 drawings for The New Yorker, including 87 covers. At the same time as his career as an illustrator soared, Steinberg was exhibiting paintings and drawings in galleries and museums. In 1946, he was included in the critically acclaimed Fourteen Americans show at The Museum of Modern Art, New York, exhibiting along with Arshile Gorky, Isamu Noguchi, and Robert Motherwell, among others. Steinberg went on to have more than 80 one-artist shows in galleries and museums throughout the US, Europe, and South America.