![\"Jacob](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/08\/CTC-L-ENT-TERRIBLE-PORTRAITS-28_232459126.jpg\")
Jacob Ryan Reno draws a \u201cterrible\u201d portrait of a group of people in Logan Square on Aug. 10, 2025. (Eileen T. Meslar\/Chicago Tribune)<\/p>\nJacob 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 \u2026 he\u2019s 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\u2019s not very good. 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: \u201cHe must be talented if there\u2019s a line.\u201d<\/p>\n
She added, \u201cI mean, what if he becomes famous someday?\u201d<\/p>\n
Then she mentioned, even more straight-faced this time, that she was an \u201cart enthusiast.\u201d<\/p>\n
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. Some acting, some performance art, a bit of stand-up, waiting tables. He radiates a rangy energy. He\u2019s thrilled to be creating anything. Maybe you know the type.<\/p>\n
Three months ago, he had an idea that he would take a folding table to the Sunday farmers market in Logan Square and draw portraits, for $5 a pop. But with a twist. He announced his services with a handprinted sign: \u201cTerrible Portraits. 5 Terrible Minutes.\u201d<\/p>\n
Since that Sunday in May, he\u2019s drawn 600 or so portraits, and become so popular via social media that he\u2019s been getting requests from a number of famous faces. Questlove wants one. The day I watched him work, he cut off the line for portraits earlier than usual because he was due at the Salt Shed that afternoon, having been asked by Wilco to draw the band before their show that night. He\u2019s just started getting hired to draw his miserable portraits at weddings and birthday parties.<\/p>\n
\u201cThe funny thing is, since starting, I\u2019m not getting better,\u201d he told me.<\/p>\n
No? I asked, wondering what his art looked like before it was merely terrible.<\/p>\n
\u201cNo,\u201d he said, \u201cI think I\u2019m actually getting worse.\u201d<\/p>\n
Fair enough. His repertoire, so far, is limited to faces and he\u2019s lousy at it. His heads resemble supermarket hams. His eyes look hypnotized or insane. He sketches hair with the sharp, slicing strokes a toddler might use to draw a haystack. His mustaches could be train tracks. His noses all look the same, like wine bottles. His mouths are bananas, as in the food. Like other visual artists, while he\u2019s working, he looks up to see what\u2019s in front of him, returns to his palette, looks up again \u2014 but I started to wonder if all that looking up was performative. I watched two very different friends get a joint portrait and after sitting in front of Reno for five minutes, the results were almost identical. Two long heads. Same black hair. Same sunglasses. They looked exactly like Oasis.<\/p>\n
Celia Simon, one of those women, studied herself on the heavy poster stock that Reno uses for his portraits. She coughed out a laugh, then, on second thought, decided she loved it. \u201cNo \u2026 god, it\u2019s actually perfect,\u201d she said. \u201cI mean, I\u2019m going to take this to my doctor\u2019s office. I keep telling them my nose looks crooked and they\u2019re just not getting it.\u201d<\/p>\n
Jacob Ryan Reno draws a \u201cterrible\u201d portrait of a group of people in Logan Square on Aug. 10, 2025. (Eileen T. Meslar\/Chicago Tribune)<\/p>\n
Jacob Ryan Reno, a native of Redondo Beach, California,<\/strong> arrived in Chicago a decade ago, for college. He attended DePaul University, studied screenwriting. The origin of \u201cTerrible Portraits,\u201d a story he\u2019s repeated many times while small-talking with whomever he\u2019s drawing, is that he and a friend from college were at a house party and decided to draw each other for fun. His friend was horrified at what Reno came up with. She asked: \u201cIs this how you see me?\u201d She was sort of kidding.<\/p>\n That was seven years ago.<\/p>\n Skip ahead to last spring, and Reno was slogging through a brand strategist that he decided \u201cdid not align\u201d with his values. He also didn\u2019t like the 9-to-5 lifestyle. So he quit.<\/p>\n About that time, he came across the original drawing from that house party and, on a whim, decided to re-create \u201cTerrible Portraits\u201d in the wild, partly for the money, partly because he likes to talk to strangers, partly because it seemed fun.<\/p>\n \u201cI was there first day,\u201d said Al Smart, his partner, themselves a sometime actor, sometime artist, sometime florist. \u201cHe was nervous. He was, like, \u2018Will people get offended? This could just be stupid.\u2019 But right away, that\u2019s not what happened. Right away, I think we kind of realized, this is a service, this is an experience. Without getting too heavy, we talked about art and how good art, no matter the medium, is about you creating for someone who is there with you \u2014 and ideally, the artist is getting just as much enjoyment from it.\u201d<\/p>\n Since that first attempt, a scene has sprung up every Sunday around Reno.<\/p>\n He sets pens in front of him. He tidies a thick sheet of paper. He waits. The other day, when I watched him make portraits \u2014 for almost three and a half hours, only taking a second to eat an empanada that had long gone cold \u2014 he was barely seated when his first client approached. Other than appearing across the street from the Logan Square Farmers Market on weekends, he pops up around Chicago during the week, at festivals, at parks. He doesn\u2019t announce where he is going on Instagram but has considered advertising his services by posting terrible self-portraits on Milwaukee Avenue that ask: \u201cHave you seen this man?\u201d He likes the surprise. At The 606 trail, a man stopped and asked him what he was raising money for. Reno said, \u201cI don\u2019t know. My vibe?\u201d<\/p>\n As he draws, clusters of hopeful muses hover nearby, waiting for their chance. They mutter that he looks like John Mulaney, which he definitely does. Reno places a speaker on the table and plays bebop. He wears a cravat around his neck, just like you know, artists.<\/p>\n No one, faced with their portraits, has gotten mad yet.<\/p>\n A 10-year-old boy, seeing his portrait, did scream, \u201cARGHHHH!\u201d And Reno screamed back, \u201cTHE HORROR!\u201d But mostly his clients make small talk about relationships and bike routes and apartments. They leave sly comments on the results: \u201cLike looking in a mirror!\u201d \u201cIt captures my beauty!\u201d Some said they liked the low stakes. Some said they could never afford, let alone show the patience, to sit for a traditional artist portrait.<\/p>\n \u201cDid you go to art school?\u201d a man asked, sincerely.<\/p>\n Reno winced and said, \u201cNOOOOOOOOOOO.\u201d<\/p>\n Still, a fair question. This could be a gag. Some wonder if he\u2019s secretly good. Another customer mentions to Reno what he\u2019s doing feels reminiscent of outsider art, or so-called naive art, the kind of self-trained, sometimes childlike work that\u2019s an art-world niche, filling places such as the Intuit Art Museum in West Town and the Art Preserve of Sheboygan, Wisconsin. Reno\u2019s portraits are never flattering, yet they offer a consistent vision. Plus, like other outsider artists \u2014 a term Reno only recently heard for the first time \u2014 he says he does this because, well, he just does it, has never thought about getting sick of it, hoping to be considered a professional artist or evolving as an artist.<\/p>\n The closest Reno gets to an artist statement is when he says that anything less than spontaneous about \u201cTerrible Portraits\u201d would feel \u201cantithetical to everything I\u2019m doing with this. I\u2019m a big believer in art everywhere, but I also think, in an age of AI-generated art and ChatGPT, I worry about if we\u2019re losing the art of communication, face to face.\u201d<\/p>\n He fears that a \u201cweird tension\u201d could develop between him and some of the people he draws, an expectation for him to draw them, as promised, as poorly as possible. He doesn\u2019t think about this as a performance.<\/p>\n \u201cI am not playing a character. I actually am trying to draw people well. I hope when people sit across from me that they know that. I hope they know that I really am trying as hard as I can, but it will probably be terrible.\u201d<\/p>\n A couple from Lincoln Park, Abby Auwaerter and Will Morris, sat across from Reno. \u201cYou know, this is actually the second time we\u2019ve sat for a portrait,\u201d Auwaerter said. The first portrait was in Key West, and it was done by the sort of traditional sidewalk sketch artist found in tourist towns.<\/p>\n \u201cBut that one,\u201d she continued dryly, \u201cwas not advertised as terrible.\u201d<\/p>\n \u201cYeah,\u201d added Morris, \u201cI mean, at least you\u2019re transparent.\u201d<\/p>\n cborrelli@chicagotribune.com<\/p>\n","protected":false},"excerpt":{"rendered":"Jacob Ryan Reno, long and boyish, wearing the kind of blue smock you imagine a painter would wear…\n","protected":false},"author":3,"featured_media":160884,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[5124],"tags":[648,960,171,5386,1818,2765,1370,1072],"class_list":{"0":"post-160883","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-chicago","8":"tag-arts","9":"tag-chicago","10":"tag-entertainment","11":"tag-il","12":"tag-illinois","13":"tag-keywee","14":"tag-latest-headlines","15":"tag-things-to-do"},"share_on_mastodon":{"url":"https:\/\/pubeurope.com\/@us\/115060679870422678","error":""},"_links":{"self":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/160883","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/comments?post=160883"}],"version-history":[{"count":0,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/160883\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media\/160884"}],"wp:attachment":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media?parent=160883"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/categories?post=160883"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/tags?post=160883"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}![\"Friends](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/08\/CTC-L-ENT-TERRIBLE-PORTRAITS-30_232459068.jpg\")
Friends Abbey Londa, from left, Becca Weisz, Lauren Smith and Francesca Sands laugh as they look at the portrait Jacob Ryan Reno drew of them in Logan Square Park on Aug. 10, 2025. Reno draws “terrible” portraits of people for $5. (Eileen T. Meslar\/Chicago Tribune)<\/p>\n