In the summer of 1938, he also studied mural painting with famed artist Diego Rivera.

Woodruff earned early recognition for his works when his paintings were excepted for a juried exhibition in Indiana and were shown in a 1928 Harmon Foundation exhibition. Woodruff was awarded a cash prize from the Harmon Foundation for his entry. He used his winning to travel to Paris. Woodruff returned to the United States in 1931 and embarked on a highly career as a teacher and administrator at Atlanta University. At the same time, patronage of Woodruff’s figurative work and watercolors was growing.

Woodruff’s work was also influenced by the time he spent in Europe. He was among a community of disaffected black artists—many of whom were expatriates, that narrated their angst about the brutalization and violence against blacks in the United States. One of Woodruff’s best known images from the late 1930 and early 1940s speaks to his keen awareness and consciousness of historical events that highlighted the disenfranchisement and dehumanization of blacks.

Woodruff’s Amistad murals at Talladega College in Alabama were “commissioned in celebration of the one-hundredth anniversary of the mutiny by African slaves aboard the slave ship Amistad in 1849.” The grand scale, curvilinear lines, muscular figures, intense color and directional elements, offer the artist’s dramatic interpretation of slaves uprising against their captors. The scale and intensity of this image also recalls the influence of Woodruff’s contact with famed muralist Diego Rivera

Conversely, Woodruff’s Georgian landscapes of the 1940s are more muted in their depiction of “tarpaper shanties, community wells, and outhouses to the extent that he frequently referred to this group of landscapes as the "Outhouse School.” In reflecting the “social realism” of the moment, Woodruff called attention to the run down housing conditions and other economic disparities in the South’s black communities.

In the late 1940s, Woodruff moved to New York where he taught at New York University for over twenty-years. He and one of his contemporaries, artist Romare Bearden, helped to found the Spiral Group. “Spiral was a New York–based collective of African-American artists that came together in the 1960s to discuss their relationship to the civil rights movement and the shifting landscape of American art, culture and politics. The group included artists Charles Alston, Emma Amos, Romare Bearden, Calvin Douglass, Perry Ferguson, Reginald Gammon, Felrath Hines, Alvin Hollingsworth, Norman Lewis, Earl Miller, William Majors, Richard Mayhew, Merton D. Simpson, Hale Woodruff and James Yeargans.”

Following a long and distinguished career, Woodruff died in New York in 1980.