Letterio Calapai had a fruitful artistic career that spanned over fifty years, during which he was deemed "a printmaker for the twentieth century" by The Chicago Sun-Times in 1984. As a child, Calapai frequented the Museum of Fine Arts in Boston and the Fogg Art Museum in Cambridge, where his exposure to works of the Old Masters would come to have a profound influence on realism in his art.
In 1928, Calapai relocated from his hometown of Boston to New York City where he enrolled in drawing classes at the Art Students League and sculpture classes at the Beaux Arts Institute of Design. In the years following, Calapai expanded his artistic repertoire to include printmaking. He explored wood engraving, developing religious and literary themes. He often used the words of authors such as William Carlos Williams and Thomas Wolfe in his artwork. In 1946, Calapai began to explore the abstract realm of printmaking, primarily as a result of his exposure to Stanley William Hayter's intaglio workshop, "Atelier 17." His images continued further into abstraction as he became interested in Social Realism, German Expressionism, and Post-Expressionism, as seen in his "Jehovah's Eye" and "La Valse." Calapai also took inspiration from nature, and experimented with organic, circular shapes and color.
While Calapai absorbed new ideas from established artists and movements, he also imparted his knowledge to promising young artists. He founded and chaired the Graphic Arts Department at the Albright Art School in Buffalo, NY (1949-1955), taught art at the New School for Social Research (1955-1965), established the Intaglio Workshop for Advanced Printmaking in New York (1962-65), and was involved with numerous other colleges and universities.
Letterio Calapai continued to explore the technical and aesthetic aspects of all artwork in his studio in Glencoe, Illinois while maintaining the tradition of teaching through his workshop.