Woodruff won an award from the Harmon Foundation in 1926,[3] which enabled him to spend four "crucial years studying in Paris from 1927–31.

Woodruff met leading figures of the French avant-garde and began collecting African art, which was a source of inspiration for many other modernists, including Pablo Picasso.

[9] He taught classes at the university's Laboratory High School, as well as for students at Morehouse and Spelman, a related college for black women.

[10] In 1936 Woodruff went to Mexico to study as an apprentice under the famed muralist Diego Rivera, learning his fresco technique and becoming interested in portrayal of figures.

After his return to the United States in 1936, Woodruff applied his understanding of Post-Impressionism and Cubism to painting and printmaking for social advocacy.

[11]In the spring of 1938, Woodruff was commissioned to work on a series of murals for the lobby of the Savery Library at Talledega College in Alabama.

The circular motion of the bodies increases the drama of the struggle...The figures are designed in an overlay fashion so that they are seen as one complete unit moving from the left bringing the eye around to the escaping sailor, who reappears in the second panel as the accuser.

The library has another series of three Woodruff murals exploring events related to the black college's role in African-American history, including freedmen enrolling after the American Civil War and the construction of campus buildings.

[14] In 1942, even with World War II raging, Woodruff initiated the Atlanta University Art Annuals, an exhibit and competition that was conducted until 1970.