Pippin followed his own idiosyncratic method for painting: Having suffered an injury in World War I that limited the mobility of his right arm, he worked on small canvases and visualized images without any preparatory drawings or sketches. He built his scenes with blocks of color and very little perspective, resulting in a graphic quality that set his work apart from that of his contemporaries and offered intimate glimpses into the world of his imagination.

Pippin drew his subject matter primarily from the activities of small-town life and likely found the inspiration for Amish Letter Writer in Lancaster County, a center of Pennsylvania’s Amish community near his home. The work was painted just as Pippin was beginning to receive attention from museums, collectors, and dealers. Robert Carlen, an art dealer in Philadelphia, took a great interest in his work and mounted his first solo exhibition in January 1940. The visionary collector Albert Barnes saw Pippin’s paintings as they were being installed at Carlen’s gallery and bought several on the spot.