From the early 1920s to the late 1940s, the painter Hale Woodruff (1900-1980) demonstrated a consistent interest in creating portraitures of New Negro types and modern landscape painting. This dissertation will be the first sustained treatment of Hale Woodruff's important career, examining the artist's treatment of these subjects in relation to his class mobility and the cultural and social forces that shaped his art. In an effort to examine the significance of these topics in the artist's work, this dissertation will look critically at the artist's career beginning in 1900 (the year of his birth) and 1946 (the year he joined the faculty at New York University. I will explore the thematic transitioning of the artist's work within four chronologically organized periods: (1) Woodruff's childhood in Nashville, Tennessee; (2) Woodruff's association with W.E.B. Du Bois and the African-American intellegencia in Indianapolis during the 1920s; (3) Woodruff's interest in landscape painting in France late 1920s and 1930s; (4) Woodruff's tenure at The Atlanta University Center, beginning in 1931.