In his earliest poetry, Oppenheimer shows clearly the influence of William Carlos Williams, but he soon developed his own style. While at Black Mountain, Oppenheimer met and married his first wife, Rena Furlong. He left the school in January of 1953 without taking a degree, eventually settling in New York and working in a print shop while continuing to write poetry.
Drawing from Life, posthumously published in 1997, gathered 92 columns written for the Village Voice. Library Journal wrote that Drawing from Life "emphasizes several favorite themes: baseball, politics, and the role of the changing seasons in our lives".