The Winfield Daily Free Press, Kansas, April 18, 1904
Flora Stacey’s typewriter works, published in 1897 but likely made even earlier. From James Ryan’s thread on the history of typewriter art.
The article The Lost Ancestors of ASCII Art shows works from a typewriter-focused magazine from 1893. The butterfly on the far right has been around the netz for a while, but middle one (by the same author, Flora Stacey) and the ship (by Frederick Carles) are new to us atleast.