List of Caldecott Medal WinnersList of the Caldecott Medal winners from 1938-2023. The Caldecott Medal was named in honor of nineteenth-century English illustrator Randolph Caldecott. It is awarded annually by the Association for Library Service to Children, a division of the American Library Association, to the artist of the most distinguished American picture book for children. The Academy of Art Library has all 81 award winning titles in our collection. Come by and check them out!