Born in New York City. As a child Glankoff taught himself to paint by copying miniature paintings he had seen at the Metropolitan Museum of Art.
Attended the 1913 Armory Show, the first international exhibition of modern art in America.
As a conscientious objector of WWI, left for Cuba, where he was falsely accused of espionage, imprisoned, and then released in 1919.
Returned to New York. Worked for Rosenberg Art Service Studio, and other art service studios, where he did woodcut illustrations, woodcut book illustrations and pen and ink advertisements.
Received a copy of Das Holzschnittbuch, the first book to publish German Expressionist woodcuts. After seeing these images, Glankoff began carving woodcuts with the grain in the German Expressionist style.
At the invitation of Juliana Force, exhibited paintings and woodcuts in the annual group shows of the Whitney Studio Club at the Anderson Galleries, for which Glankoff (Glanckopf) received critical acclaim from The New York Times.
Began living with Frances Kornblum, his partner for forty years. Glankoff and Kornblum spent the majority of their time in Woodstock in a large one-room stone house, where the attic served as Glankoff's studio.