David Small was born on February 12, 1945, in Detroit, Michigan. He studied art and English at Wayne State University, and went on to complete graduate studies in art at Yale. After receiving his MFA degree, he taught drawing and printmaking at the State University of New York, Fredonia College, Kalamazoo College, and the University of Michigan. He also created editorial cartoons for publications such as the New Yorker, the New York Times, and the Wall Street Journal. In the 1980s, he lost his teaching job due to cutbacks. It was then that he committed himself to combining his loves of writing and art.
His first picture book, Eulalie and the Hopping Head, was published in 1981. He earned a 1997 Caldecott Honor and The Christopher Medal for The Gardener, written by his wife, Sarah Stewart. In 2001, he received the Caldecott Medal for his artwork in So, You Want To Be President? by Judith St. George. His editorial drawings regularly appear in publications such as The New York Times, The New Yorker, GQ, and The Washington Post.
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