Emoticons in 1881, via Retronaut. Some more digging indicates these “typographical art” originated in the magazine Puck. [h/t @MAlexJohnson]
It was probably a major pain in the butt to do this with a letterpress in 1881. Still very much worth it though.
Eh, by 1881, depending on where you lived, you’d have a linotype machine so you no longer had to set everything by hand. Would have made it much simpler! And as someone who has some experience setting type in a living history museum, you get pretty quick at it. I’ve never seen faces like this before though!