Working in collaboration with his wife Diane, Leo Dillon illustrated award-winning children's books and designed covers for many mass-market paperback books, especially science fiction titles. Leo Dillon, of Trinidadian immigrant parentage, was raised in East New York. He joined the Navy for three years to fund art school. Dillon met Diane Sorber in 1953 at the Parsons School of Design in New York City, where they both studied. They graduated in 1956 and married the following year.
The Dillons collaborated for more than 50 years, coming to see their work as that of a third artist. They won a 1971 Hugo Award for science fiction illustration, Caldecott Medals for children's books in 1976 and 1977, and in 1978 they were the runners up for the Hans Christian Andersen Award.