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Terrible Chicago artist draws terrible Chicago portraits

Gulf Today

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August 27, 2025

Jacob Ryan Reno, long and boyish, wearing the kind of blue smock you imagine a painter would wear in a cartoon about a painter, is not good at his job. He draws and has become pretty popular in Chicago for those drawings. Yet... he's so bad at it. So bad he inspires a perverse confidence in that lack of talent, partly because he warns everyone with a sheepish smile that he's not very good.

- Christopher Borrelli, Tribune News Service

When I asked a woman in Logan Square why she was waiting for Reno to draw her portrait, despite knowing his skills were questionable, she replied, with irony: "He must be talented if there's a line." She added, "I mean, what if he becomes famous someday?"

Then she mentioned, even more straight-faced this time, that she was an "art enthusiast." And Reno, for sure, is an artist, a young Chicago one, just 26, and all that entails, doing a little this, a little that, living in Logan Square.

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