The first use of emoticons in print came in the March 30, 1881 issue of Puck magazine. You can see the faces of joy, melancholy, indifference, and astonishment in a short piece about ‘Typographical Art’.
Puck was an American magazine of political satire and other humor, published in English and German editions in the 19th and early 20th century. The full text of Puck magazine can be accessed through the HathiTrust. The HathiTrust is a partnership of academic and research institutions, offering a collection of millions of titles digitized from libraries around the world.