Hopper’s enigmatic paintings look into the hollow core of the American experience—the alienation and loneliness that represents the flip side of to our religious devotion to individualism and the pursuit of an often-elusive happiness. In compositions such as Nighthawks, Automat and Office in a Small City, he captures stillness weighed down by despair, his subjects trapped in the limbo between aspiration and reality. His landscapes are similarly suffused with a sense that America’s open spaces are as purgatorial as they are limitless.

Edward Hopper, Self Portrait, 1906