[4] After a short stint as an illustrator for the U.S. Navy, Gottlieb moved to New York City; he became a scenic and costume designer for Eugene O'Neill's Provincetown Theater Group.

In 1935, he joined the Federal Art Project (FAP); he was one of the first members of the WPA/FAP's Silk Screen Unit, along with Anthony Velonis, Elizabeth Olds, Hyman Warsager and other fellow printmakers.

[5][6] Gottlieb remained active as a painter and screen printer after the closure of the Federal Art Project, and served as the first director of the short-lived American Artists School in New York City.

Art historian James Watrous wrote in 1984: "The mounting interest in printmaking with silkscreen was affirmed by several other events that occurred around the turn of the decade.

In March 1940, the ACA (American Contemporary Art) Gallery sponsored the second one-man show of silkscreens, a display of prints by Harry Gottlieb.

Among the twelve works was Winter on the Creek, elaborately printed with eleven colors that projected a picturesque scene of ice skaters in a seasonal American landscape.

Gottlieb and other artists, including Warsager and Leonard Pytlak, "often chose to ignore a graphic aesthetic and seized the opportunity to use many screens, colors and complex printings in order to simulate the nuances and illusions that usually had been reserved for watercolors and oils.