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The novelist Richard Wright, who migrated from Mississippi and spent his formative years in Chicago, got pounded by the city's drama. But in time he came to admire it. Wright later wrote: "There is an open and raw beauty about that city that seems either to kill or endow one with the spirit of life."

Such is the predicament of Robert Guinan, a painter, who is one of Chicago's keenest observers. He can't decide whether to celebrate or grieve the city's passages. The city in recent years has undergone a remarkable transformation: the prettification of the Loop and surrounding neighborhoods, an explosion of new and renovated houses, the opening of Millennium Park, even gondola rides on the Chicago River. Some, like Guinan, fear that with such changes the city will become like any other, that it will no longer push and pelt the senses, that it will lose its poetry. For Guinan, Chicago has always been an exotic place—like Bombay or Istanbul—and he doesn't want anything to dampen that.

Guinan, 71, is a slender man who wears an expression of constant amusement. For nearly 30 years, he has been painting the underside of the city, sketching the homeless and prostitutes, barmaids and immigrants, hustlers and blues musicians. His paintings have been compared to Edward Hopper's and sell for upwards of $60,000. Ironically, he's been virtually ignored in Chicago, his home and the subject of his work. But he's adored in France, a place, like the rest of Europe, that seems obsessed with Chicago, America's city. (An Italian television crew is filming a series here because, the producer told me, "We want to understand America.") This summer, Guinan is being honored with a retrospective at the Villa Medici, the French Academy in Rome. He's never, though, had an exhibition in Chicago. His neglect might be reason for bitterness, but Guinan says he's just glad that his work is appreciated somewhere, and, besides, he's in good company. Chicago often turns away from its own. The novelist Nelson Algren, who always felt shunned here, and who eventually left, in 1961 wrote that "anyone in Chicago can now become an expatriate without leaving town."

I met Guinan for lunch recently at the Cliff Dwellers, a 98-year-old club for the city's painters, writers, and musicians. From the penthouse location overlooking Lake Michigan, the view may be the most awe-inspiring in the city. On a clear day you can see the aging steel mills 15 miles south, once the source of America's industrial might. Guinan and I have a table by the window, and together we take in the winding lakefront, which is what allows the city to breathe. (Bordering Lake Michigan is the equivalent of having a city butt up against a 22,300-square-mile tract of wilderness.) Just to the south is Soldier Field, the stadium that houses the Chicago Bears. It opened in 1924 as a memorial to American soldiers, and for decades resembled a Roman coliseum (leading Studs Terkel to comment, "Every time I go by it I just want to say, 'Bring out the lions! Bring out the lions!'"). But it was recently renovated, and in an effort to preserve the old, they added onto and reshaped it, so it appears as if the Starship Enterprise crash-landed on a Neoclassical structure. It is, I tell Guinan, one odd sight, especially from above. Guinan shakes his head, and while I figure this is an opening for him to riff on the loss of what first seduced him about the city, he says simply: "I love this place. I'm sure there's plenty of old Chicago left, you just have to look harder."

Guinan is still painting, and is working on a portrait of members of a motorcycle gang: meaty, self-absorbed young men in black sleeveless tees. He sketched them 15 years ago at a tavern called the Double Door, a former country-and-western honky-tonk that morphed into a rowdy biker bar and is now a more refined music venue for the young professionals and artists who have moved into the neighborhood. I asked Guinan if, in the end, he feels the exotic Chicago is lost to the past. He tells me about a 1940's Life magazine article in which an elderly musician, speaking of the city's jazz age, told the magazine: "This was Chicago then, but nothing has happened since." Guinan laughs. "What he didn't know was that the late forties was the beginning of Muddy Waters and the Chicago blues." His point is this: the city is constantly reinventing itself, and while some things pass, there's always something waiting, usually something equally real and alluring.

Guinan likes to tell people that he can't go out anymore to sketch because he can no longer drink or smoke, and so what fun would it be?But after two glasses of red wine over lunch, he recounts the time not long ago when a friend brought him to a bar on the corner of Halsted and Milwaukee; it didn't have a name, just an Old Style sign in the window. The bartender was named Rocky, and one of the men there, a union guy, started talking about Machiavelli. Guinan was taken with a young woman at the bar, and so he sketched her on the back of a pizza box. "I smoked Marlboros, I drank Scotch," he said. "God, I enjoyed that night. It was like old times." But that's the thing. Chicago will always be smoking and drinking, and it will always have bars without names, and its men and its women will forever be discussing the great philosophers and how to make a buck. It's the beauty of this place: that even with all that's new, it's always like old times. Guinan understands that better than anyone. "We're surrounded by beauty," he tells me, paraphrasing a Sufi poet. "But we usually have to be walking in the garden to notice it....Let's face it, this place is alive."


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