Hobson Pittman is highly regarded for his reminiscent and slightly mysterious landscapes and interiors which captured moments of reflection or recalled memories–real or embellished–of his youth. He gained widespread recognition from reproductions of his paintings in Life magazine. He was on friendly terms with Clare Boothe and Henry Luce, the head of Time Life and owners of Mepkin Plantation near Charleston, South Carolina. Pittman visited them there and painted a majestic scene of the grounds when it was in full flower. 

Pittman was born in Epworth, North Carolina, a crossroads town in the eastern part of the state dominated by his family’s general store, home, and the church they had built. When he was six years old the family moved to nearby Tarboro, and soon afterward he displayed an interest in art. He studied at the local Rouse Art School from 1912 until 1916. The loss of both parents before age 16 spurred him north, towards his already established sisters. After graduation from high school he attended Pennsylvania State College, 1921–1922; the Carnegie Institute of Technology, in Pittsburgh, 1925–1926, and Columbia University, in New York, 1926–1928. Beginning in 1920, and for the ensuing eleven years, he spent his summers in Woodstock, New York, a thriving art colony in upstate New York, where both Birge Harrison and Alfred Hutty resided seasonally.

As a teacher Pittman was much in demand. Starting in 1931 he took the position of Director of Art at the Friends Central Country Day School, located in a Philadelphia suburb. He remained there for twenty-six years and during summers he taught at Pennsylvania State College, the Philadelphia Museum of Art, and the Pennsylvania Academy of the Fine Arts. He lived in an old carriage house in Bryn Mawr surrounded by two acres of formal gardens. 

A critic once called Pittman a poet-painter because of the nostalgic haze that typifies his still lifes, landscapes, and interiors. His use of pastel in particular augmented this sensibility. Indoor scenes—such as his series of Charleston drawing rooms that appeared in Life—recall earlier, more elegant times and are characterized by a quasi-surrealist sense of absence: no people and empty chairs. 

For Pittman both nature and museums were important sources of inspiration, as he once indicated: “It is difficult for an artist to put into words how he feels about his work, but I firmly believe in the keenest observations of nature and a constant study and reflection of the museum at large. These are the best teachers. It is the assimilation of all this that one uses as a painting vocabulary, but be reminded that a personal translation should take place. The artist ‘sees’ his way and there is a difference between an artist and a painter.”