Cottingham is best known for his work depicting cropped close-ups of the building facades, shop fronts, and signage of American cities, an interest that began during his childhood in New York with visits to Times Square. At twelve years old, Cottingham had what he called a "seminal moment" at the Whitney Museum of American Art in New York. Wandering through the galleries, he came across one of Edward Hopper's most iconic paintings, "Early Sunday Morning." Cottingham said, "It was the first time I realized that a painting could talk to you. Here was something that was feeding back to me. I had discovered another language - a silent language. It not only determined how I would paint - that I would be a realist painter - but it determined that I WOULD paint." After spending some time in London and finding the city signs too foreign, Cottingham settled in rural Connecticut, when he painted "Barber Shop." This particular watercolor is eerily reminiscent of the barber shop pole and store front in Hopper's "Early Sunday Morning." Cottingham filled in some of the details, such as the text on the sign behind the barber pole. Many of Cottingham's paintings show an interest in typography and lettering, aligning with his former career in advertising. Cottingham painted the watercolor of "Barber Shop" in 1987, revisiting the scene a year later as an oil painting. The text on the signage is slightly altered from one version to the next.