ASCII Art in 1939 (Jun, 1939)
Yes, I know the ASCII standard wan’t established until 1967, but it’s the same general idea.
Typewriter Artist Produces Pictures Like Tapestry
Pictures that resemble tapestry are produced with a typewriter by Rosaire J. Belanger, a mill worker in Saco, Me. Belanger first draws a pencil sketch on a sheet of paper, then inserts it in his typewriter and fills in the sketch with various characters to produce shading and outlines. With carbon paper, he transfers the picture onto graph paper, and copies it on blank paper.