The Great Gatsby (Scribner's, 1925)

Francis Cugat's jacket for the April 1925 Scribner's first edition: a pair of eyes and red lips floating in a night-blue sky above the glare of a fairground city. Cugat delivered the painting in 1924, before the novel was finished, and Fitzgerald asked his editor Maxwell Perkins to keep the jacket for him because he had written it into the book. Readers have tied those eyes to the billboard of Doctor T. J. Eckleburg ever since. This copy wears the first-issue jacket, which prints "jay Gatsby" with a lowercase j on the back panel.