In building the Sears Tower, Chicago—the city with broad shoulders that longs for a higher profile—may have realized its ideal self. Ideal not for boosting the city’s architectural stature, but because the Sears Tower looms over the World Trade Towers and every other building in New York City. The relation between art in Chicago and New York has always been similarly uneven, but here it is New York that casts the shadow.

If the insecurities of Los Angelenos have been soothed of late by the success of a Lari Pittman, Chicago’s ego proves more vulnerable. Many critics outside that city simply would not acknowledge the relevance of even imagist Ed Paschke to the history of American painting. And Paschke surely presides as Chicago’s cardinal figure. Or maybe the fundamentally “outside” Henry Darger better represents Chicago: an imaginative, genuinely perverted amateur to Paschke’s conventional, laboriously perverse pro. Darger’s little Brownies, sporting whimsical genitalia and short dresses, make the Hairy Who look like Cub Scouts working on their first badges.

“Art in Chicago, 1945–1995,” at Chicago’s Museum of Contemporary Art, surveys art made in Chicago since 1945. In five chronological sections, the exhibition presents a history that is inclusive rather than streamlined, swollen by the work of 150 artists. The organizers (led by curator Lynne Warren) define Chicago art, but broadly: what we see is surrealist, figurative, expressive, political, tactile, humorous, craft-oriented, independent. A slice from almost any point in the installation would reveal several of these “tendencies.” (As if this multiplicity were insufficient, the final decade is titled “(Un)assigned Identities,” unraveling all historical threads.) The refusal to pare down “Art in Chicago,” either in scope or by privileging quality, combines with the often rough nature of the work to create an environment reminiscent of a garage sale.

Disparate artworks find common cause in resisting the history of “advanced” postwar American art (read that of the New York art world). Chicago artists as a rule are more eccentric than avant-garde, but exceptions did enlist in the standard movements. Emerson Woelffler’s AbEx canvases seem thickly stagnant (second-rate abstractions in New York are no better, only less often praised); much more vital are contemporaneous works by better-known figurative artists H. C. Westermann, Nancy Spero, and Leon Golub, as well as influential photographers Aaron Siskind and Harry Callahan. At the other end of the exhibition, Hirsch Perlman’s deadpan photo- and text-based work nods to Conceptual art, a “non-Chicago” movement; Perlman’s surface hipness becomes orthodox, self-conscious theorizing in the accessible glow of a nearby Kerry James Marshall. While little of the successful work here predictably challenges its antecedents (i.e., makes “progress”), intimations that life exists undisciplined by the mainstream avant-garde may be more subversive than that avant-garde itself.

In their catalogue essays, Peter Selz and Franz Schulze (like Chicago critics rather than Chicago artists) insist on Chicago art’s relationship to Modernism. Schulze speaks in the authoritative voice of Modernist architecture in Chicago: “Mies, it would seem, regarded paintings and sculptures ideally as counterfoils to architecture, not imitations of it.” “Mies” anticipates and steps in to mediate not only Chicago art’s perceived anti-Modernism but specifically the tension between Josef Paul Kleihues’ spanking-new building for the MCA, which willingly joins the Modernist tradition, and the art inside, which refuses to. New York’s artistic hegemony rests partially on how good its clean, “timelessly” formal art looks in its clean, modern museums. Much of Chicago’s art-mural paintings, Don Baum’s pediment of plastic dolls-was not only deliberately unpolished, but deeply imbedded in its moment, the now (now “then”) rather than the eternal. Stored in Kleihues’ refrigerator of a building, the art loses the scent. Funk fades.

To revive the art, the curators have installed three small rooms that attempt to synchronize the time of the art objects and that of the containing museum. Two of the rooms reconstruct important exhibitions of the Hairy Who (originally James Falconer, Art Green, Gladys Nilsson, Jim Nutt, Suellen Rocca, and Karl Wirsum) and early ’80s graffiti/expressionism; the third documents late ’60s political art. These time capsules resolve art’s battle with architecture by simply effacing the latter—with wallpaper, black light, and video loops. They also suspend quality judgments by constructing a context (whether political or aesthetic) for the art, art that now testifies to “what happened.” While slightly disorienting, these tableaux give better history than the standard, drive-by didactic wall texts.

After leaving the exhibition, I called two art historians, one from Chicago and one from New York. The former loved the exhibition and hated the museum; the latter loved the museum and hated the exhibition. Depending on whom you ask, “Art in Chicago” succeeds, one way or another. While New York’s MoMA strained to reconcile high and low, and Los Angeles’ County Museum of Art isolated Outsider art in a separate exhibition, the MCA incorporates these odd elements easily, making it all look livable, without too much talking down (or up). One could say that Chicago embraces amateurs, unlike New York, which insists on, and manufactures professionalism. If success is a job in New York, maybe happiness is a studio in Chicago.

Katy Siegel is assistant professor of art history at the University of Memphis.