Chicagoans do not always welcome critiques of their city by outsiders.

Take Rachel Shteir. In a now infamous essay for the New York Times last April, the DePaul University professor and New York native confessed she was “bugged by Chicago’s swagger,” given its laundry list of economic and social problems. She even called out some local writers for perpetuating the “bloviating.”

The response, at least here, was swift, severe, and resoundingly negative. Shteir had more than touched a nerve. She started a fight.

So when Dieter Roelstraete decided to curate an exhibition about Chicago—currently running at the Museum of Contemporary Art—and include work by artists from outside the city, he was well aware he too might “rile” people.

“This is a city that likes to talk about itself, and doesn’t like other people talking about it, which is true of many cities,” said Roelstraete, whose installation is called City Self. “So this show for me is a little bit of an experiment. Because I myself go out on a limb.”

Consisting largely of photography, Roelstraete says City Self functions as kind of a “dialectic” about Chicago: between the views of insiders and outsiders, from both bird’s eye and “from within the bowels” points of view.

Works by local artists such as cartoonist Chris Ware and photographer Jonas Dovydenas present up-close, mainly warm, and people-centric views of Chicago’s neighborhoods and ethnic communities. Alongside those are works that cast what Roelstraete calls a “forensic” eye on the city.

Ruth Thorne-Thomsen and Tom Van Eynde capture small, enigmatic scenes that convey a sense of desolation and at times disaster. Catherine Opie and Andreas Gursky’s epic photographs of Chicago’s economic and architectural infrastructure render the city as a dazzling, if impersonal, space. The show’s centerpiece unfolds on a floor-to-ceiling screen housed in a long, dark, rectangular gallery. Chicago, a 2011 film by Sarah Morris, is a spectacular, almost glistening panorama of the city.

Chicago takes a very familiar and even boosterish point of view. There are long, repeating shots of well-worn tourists spots such as the John Hancock Building and Manny’s Deli. Regular Chicagoans hang out at the beach, eat lunch, and motor down Lake Shore Drive. Former Mayor Richard M. Daley holds a press conference.

But all of it has an uncanny air. Morris’ camera wanders through spaces that are now shuttered, such as the former Ebony Jet Magazine offices. She films industry that has largely vanished (meat packing, much of local newspaper publishing). All ambient sound is stripped away. Instead, everything plays out over a minimalist (and eventually annoying) electronic beat. If the film comes across as an advertisement, it is for something nobody seems interested in buying anymore.

Roelstraete said Morris’ film inspired the show’s theme.

“Her obsession with surface is duplicated in quite a few of the works by outsiders who really don’t care so much about getting to know the city,” he said. “They’re kind of more interested in this slightly alienated spectacle of the modern metropolis.”

Morris is an outsider. She is British and lives in New York. But in a post-screening discussion, she revealed that her ability to make this film relied on her connection to the most insider of insiders: Penny Pritzker, the Chicago billionaire-businesswoman currently serving as U.S. secretary of Commerce.

That complicates the insider-outsider dynamic that Roelstraete is attempting to explore. And though Roelstraete too is an outsider — he moved here from Berlin less than a year ago — he seems less interested in Chicago as a specific locale, seeing it as the “quintessential American city.”

“Just the intensity of gun violence, or the byzantine complexities of bipartisan politics in this country,” said Roelstraete. “So if there is a dark undertone, I guess it is the dark undertone of American society as a whole.”

City Self is at the Museum of Contemporary Art through April.

Alison Cuddy is an arts and culture reporter at WBEZ. You can follow her on Twitter , Facebook and Instagram.