Born in Boston, Massachusetts in 1902, Letterio Calapai studied at the Massachusetts Normal Art School, the School of Fine Arts and Crafts, Boston, and with portrait painter and watercolor landscapist Charles Hopkinson. He later moved to New York City where he continued his studies at the Art Students League and the Beaux Art Institute of Design.
While in New York, Calapai became a member of Atelier 17 where he studied with British printmaker Stanley Hayter, and began to take up printmaking. He became interested in German Expressionism and Post-Expressionism. It was at this point in his career when his work became more abstract, fantastical and imaginative.
He later moved to Glencoe, IL where he set up his own workshop.
During his lifetime he exhibited at the Salons of America, Pennsylvania Academy of Fine Arts and Art Institute of Chicago, among others. His work is included in the permanent collection at the Metropolitan Museum of Art, Fogg Art Musuem, Cambridge, MA, Boston Museum of Fine Arts, and Bibliotheque National de France, Paris, among others.