tomorrow I'll be shaking up the early history of another niche area, typewriter art, where the oldest extant examples are these (1893/1898)
in this thread, I'll be tweeting rediscovered 1800s typewriter art, including a new set of oldest extant works—current record is this (1893)
sources call Stacey's 1898 butterfly (left) the second earliest example, but six of her works were published in an 1897 newspaper (right)
in 1895, the Chicago Tribune held four contests for typewriter art and received many entries—here's winners from the two I could turn up
this forgotten 1895 piece is by Frederick Carles—a pioneer of the form who doesn't get the nearly the amount of credit afforded to Stacey
it turns out that Stacey's 1897/1898 butterfly was actually first published in 1893, a few weeks after her "Santa Maria" first appeared
I thought these set a new record, but it turns out that @alexismadrigal already included them in this great article: https://www.theatlantic.com/technology/archive/2014/01/the-lost-ancestors-of-ascii-art/283445/
this 1892 bicyclist by T. F. Adams probably doesn't count, & if it does, it's predated by e.g. H. C. Dodge's work of 1883 (h/t C. Philippo)
but Frank Baunelle's 1892 piece depicting a hunter and his dog certainly does count—apparently this lengthy verse (right) is embedded in it!
which was barely preceded by another 1891 example—the earliest non-lettering example I could find—which seems to have appeared anonymously
if we include lettering examples, we can go back further—this is how the classifieds section of the Brooklyn Daily Eagle looked in 1890-91
Ballou's was pioneering the form in ads posted in the New York Times in early 1860, and they seemed to have influenced others (later 1860)