The author reflects on the notable people he met during his career as a caricaturist and portrait artist, including his work for Vanity Fair. Using the pseudonym "Spy," he published over 1300 portraits in the magazine.

'When Winter Comes to Main Street' is a collection of book author profiles written by Grant Overton. The authors featured are those who are working with the American publishing company George H. Doran Company, namely Hugh Walpole, Rebecca West, Irvin S. Cobb, Frank Swinnerton, Steward Edward White, Mary Roberts Rinehart, Stephen McKenna, and W. Somerset Maugham.