Raised in Danville, Illinois, Carl Woosley moved with his family to Indianapolis in 1921 and then to Long Beach, California in 1922. By this time, Woosley had taught himself how to paint, but he also received brief instruction from the artist Henry Richter in Long Beach. In 1925, Woolsey's father, Charles, moved the family back to Indianapolis where Carl continued his self-instrcution in fine art.
Woolsey became intrigued with Taos after viewing an exhibition in Indianapolis of paintings by Walter Ufer, a founding member of the Taos Society of Artists. He soon started a correspondence with Ufer who invited him to Taos. Woolsey arrived there with his wife and two children in 1927 and immediately started to work by painting in Ufer's studio. His skills blossomed under Ufer's informal instruction, and he enjoyed almost immediate critical success. His paintings were juried into the Hoosier Salon in 1927 and into the National Academy of Design Winter Show in 1928. In the following years he showed in twelve more Hoosier Salons, and participated in most National Academy exhibitions until 1936. Woolsey also exhibited at the Corcoran Gallery, the Pennsylvania Academy of Fine Art, the Museums of Art in Akron and Dayton and the Stanford Gallery in Palo Alto, California. He won many prizes including the National Academy's prestigious Hallgarten Award.
Throughout his career Carl Woolsey painted landscapes almost exclusively, with small figures rarely appearing in his work. He used naturalistic color and painted in a traditional, representational style but his often complex compositions are clearly owed to Walter Ufer and to the eastern modernists. With a dappled brush and careful control of light and shadow, Woolsey emphasized shape, contour and texture which also gave his best paintings a slight modernist edge.