Christenberry received his bachelor's (1958) and master's (1959) degrees in fine arts from the University of Alabama, studying under abstract expressionist Melville Price. Beginning in 1968 he taught at the Corcoran College of Art and Design in Washington, D.C.His artistic career began with the painting of large abstract-expressionist canvasses, but gradually he began to be drawn to material that spoke about the place of his childhood. Although he was raised in Tuscaloosa, Christenberry spent his summers with extended family in rural Hale County. After graduating from the University of Alabama and beginning a promising, if not immediately rewarding, artistic career in New York City, he came across the 1941 book, Let Us Now Praise Famous Men, in which James Agee describes in prose, and Walker Evans in photographs, the experience of living among the dirt-poor farming families of Hale County during the Great Depression. Some of Evans's photographs made a deep impression on Christenberry.
One of the results of this pilgrimage was a series of photographs documenting the decay of individual structures, which are photographed as nearly isolated objects. In 1974, Christenberry began translating some of these photographed buildings into detailed sculptures that accurately reproduce their state of decay and patina. Although detailed and properly proportioned, Christenberry did not refer to these creations as models, as he says they are not based on precise measurements, and he preferred that they be called sculptures. The bases for these sculptures often are set in soil taken from these places. On many of these trips, Christenberry collected old advertising signs and other found objects which inspired him. Some of these are incorporated into his work, while others hang in his studio.