In 1925, Douglas intended to pass through Harlem, New York, on his way to Paris to advance his art career. He was convinced to stay in Harlem and develop his art during the height of the Harlem Renaissance, influenced by the writings of Alain Locke about the importance of Harlem for aspiring African Americans. While in Harlem, Douglas studied under Winold Reiss, a German portraitist who encouraged him to work with African-centric themes to create a sense of unity between African Americans with art. Douglas worked with W. E. B. Du Bois, then-editor at The Crisis, a monthly journal of the NAACP, and became art editor himself briefly in 1927. Douglas also illustrated for Charles S. Johnson, then-editor at Opportunity, the official publication of the National Urban League. These illustrations focused on articles about lynching and segregation, and theater and jazz. Douglas' illustrations also featured in the periodicals Vanity Fair and Theatre Arts Monthly. In 1927, Douglas was asked to create the first of his murals at Club Ebony, which highlighted Harlem nightlife.