An exhibition created through an unusual collaboration between Carnegie Museum of Art and The Studio Museum in Harlem will open this weekend with music, a family-friendly participatory artwork, food trucks, an artists’ discussion and a workshop.

It comprises works by 20 artists from each institution chosen by Eric Crosby, Carnegie curator of modern and contemporary art, and Amanda Hunt, director of education and public programs at the Museum of Contemporary Art in Los Angeles and former Studio Museum associate curator.

The curators selected works that reflect aspects of the changing American socio-cultural climate from the 1920s to the present. The intent is to inspire consideration of the nation’s complex history and of the role that art may play in inspiring discussion during transformative times.

When the curators began organizing “20/​20: The Studio Museum in Harlem and Carnegie Museum of Art,” Barack Obama was still president. “It’s very interesting how things shifted over the course of planning the exhibition,” Mr. Crosby said. As they structured the show, they made changes in response to “the polarized political landscape we find ourselves in.”

While the focus, in part by virtue of the particular collections drawn from, is on the way American history has impacted communities of color, the curators aim for an inclusivity that invites examination of identity diversity including generational difference, gender, sexual orientation, and urban and rural similarities and differences.

Art at its most compelling, after all, is about the human experience as told, Mr. Crosby said, “through story, through materials, through metaphor.”

Ms. Hunt and Mr. Crosby open the dialogue with their own conversation, available in a gallery guide and to be posted at storyboard.cmoa.org. But they invite each visitor to construct his or her own while traveling the show’s six themed sections.

The stage is set by “Abe Lincoln’s First Book,” a 1944 oil painting by the notable African-American self-taught artist Horace Pippin (1888-1946). Lincoln is depicted in a darkened space reaching toward enlightenment.

Mr. Crosby calls the artist’s inspiration an “idealized quest that feels so compromised today” at the beginning of the printed conversation, but by the end finds resolution of sorts in works by contemporary artists such as Howardena Pindell and Kerry James Marshall who echo Pippin’s “desire to insert our most resolute democratic values into a conversation that only art can have.”

Ms. Hunt replies, “We’ve come full circle then: We are looking back but also forward.” She cites Collier Schorr’s “The First Lady (Diplomat’s Room, Rihanna, 20 Minutes),” a 2016 photograph of Michelle Obama, “a black woman in the white space of the White House. ... The potency and potential of that image, what it allows, and the opportunity for some viewers to see themselves reflected in it. That is what President and Mrs. Obama did for an entire generation of children in this nation.”

Between these poles is a mini-exhibition of its own comprising 13 photographs each by Charles “Teenie” Harris (1908-98) and James VanDerZee (1886-1983).

“A conversation between the work of these two icons has never been presented before,” Ms. Hunt says in the printed conversation. “I’m super proud that we are able to do that. ... [Teenie Harris] documented a time in American history and, more specifically, [Pittsburgh] black history, in the way that James VanDerZee did for Harlem.”

A vital aspect of “20/​20,” Mr. Crosby said, is that it is a collection exhibition (as opposed to one drawn from a variety of sources). “The subtle gesture of re-contextualizing the works reveals different meanings.” As example he gave the Pippin exhibited alongside prominent African-American contemporary activists Glenn Ligon and Pope L. as opposed to its usual home in the permanent collection galleries beside an Edward Hopper.

At a moment when even families appear to be having difficulty initiating constructive dialogue, the curators are drawing upon natural facilitators to help.

“Artists are very special people,” Mr. Crosby said. “In some ways the conversation comes more naturally to them.”

–M. Thomas

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