The term “cool” has become such a part of America’s modern lexicon that it seems to have lost its meaning. This stellar collection of photographs from the National Portrait Gallery and from prominent artists, museums, and archives nationwide would argue otherwise. The idea of cool is not only older than we think—it’s also constantly changing, aided by the mediums of portraiture and film. Readers will find unexpected and familiar faces here: Walt Whitman, Frederick Douglass, and Georgia O’Keeffe, as well as James Dean, Bob Dylan, and Chrissie Hynde. In perceptive essays, Joel Dinerstein investigates the evolution of cool from the 1930s to the present while Frank Goodyear explores how the mediums of film and photography have helped define the term. An extensive selection of one hundred chronologically arranged portraits, with biographical information about each subject, profiles major eras and movements of the past decades, each with its own brand of coolness. Exploring cultural icons, this volume encourages readers to find new meaning and depth in the idea of American cool.