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It's like, the closer the reproduction of its subject the harder gleaning meaning from the painter expressing it. We look for warbles, imperfections in the representation, as some sort of clue, some sort of drip as content declaring its expression. "...appear to be silkscreened when they were in fact hand-painted." But the painters lack of "expression" leaves the information all the hamfistedly plainer. "Look" declares the painter. "But surely something else, too!" responds the viewer. And we become anthropologists to a receipt, what we've recieved, deciphering for the overflow of content we expect must be there. Like On Kawara, the reaching attempt for the sign to fully contain what it denotes and the distance from it actually, a single day or a free coffee, is the pathos of its content. Open your own wallet and see the days. This distance, this nostalgia, is the loss, the pathos deployed.
See too: On Kawara at the Guggenheim