When she took up painting in the late 1930s, Janet Sobel was a housewife in Brooklyn.

Her early efforts recalled the folk art of her native Ukraine, but she soon revealed a flair for the experimental. Using enamel paints and glass pipettes, Sobel began dripping color onto her paintings in abstract patterns.

Her work caught the eyes of surrealists Max Ernst and Andre Breton and went on to influence Jackson Pollock. Peggy Guggenheim—doyenne of New York’s avant-garde art scene—gave her a solo show in 1946. And the Museum of Modern Art later acquired two of her works.

Today, Sobel’s pole-vault into the art-world vanguard seems a stunning anaomaly, but back then works by self-taught or folk artists were part of many modern-art museum collections, said Lynne Cooke, a senior curator at the National Gallery of Art in Washington, D.C.

A show curated by Ms. Cooke—Outliers and American Vanguard Art—opening at the museum on Sunday—explores why and how to change that. The show brings together over 270 works by more than 80 artists—an eclectic mix of art-world stars, acclaimed un-schooled artists, and less known creators of all stripes.

“This is not a history of folk art or self-taught art,” Ms. Cooke said. “It’s an exploration of the way the contemporary art world—the vanguard American art world—has engaged with this work.”

Outliers is organized in three sections, reflecting three eras in American culture when exchanges between outsiders and mainstream art were intense: between the two World Wars; the late 1960s to the early 1990s; and the late 1990s to 2013. All three were “moments of social, political and cultural unrest,” said Ms. Cooke, when traditional boundaries between mainstream and margin, insider and outsider, frayed.

Painter Horace Pippin exemplifies that process. Pippin was considered a self-taught artist who came to prominence in the 1930s amid a rising interest in folk art and other quintessentially American cultural expressions. As he became more of an art-world insider, with his work shown and acquired by major museums, the “self-taught” label, and its connotations of naiveté and unsophistication, no longer quite fit.

By the end of his career, “there’s a spectrum of perceptions” and confusion around Pippin’s work, said Ms. Cooke. “Either he’s a remarkable self-taught artist or he’s no longer a self-taught artist. Or he never was one.”

The same might be said of other untrained artists in the show, such as William Edmondson and Bill Traylor, whose retrospective opens in September at the Smithsonian American Art Museum.

At the other end of the spectrum, trained artists like the modernist painter Marsden Hartley—who exhibited in Europe alongside Wassily Kandinsky and other cutting-edge artists—might opt for a deliberately naïve style when the subject demanded it. Case in point: Hartley’s 1918 work Blessing the Melon (The Indians Bring the Harvest to Christian Mary for Her Blessing) was in spired by a type of devotional painting common in the Spanish-speaking southwest.

Other artists in the show applied modernism’s spare, reductive style to depict folk-art objects. Charles Sheeler, known for sharply geometric paintings and photographs of industrial sites, took that approach in his 1917 photographs of a hand-built 18th-century house in Pennsylvania.

Along with little-known self-taught artists like Sobel, the show’s discoveries include trained artists whose work rarely appears in museums these days. Sculptor H.C. Westermann studied at the School of the Art Institute of Chicago but maintained a careful distance from the art world. His Walnut Box (1964) combines exquisite woodworking with a whimsical approach to subject matter, in a beautifully crafted container filled with—what else?—walnuts.

Westermann’s independent career path inspired a later generation of Art Institute grads also on view at the show, including Roger Brown, Gladys Nilsson and Jim Nutt of the Chicago Imagists group.

Outliers also spotlights artists who are gaining (or regaining) art-world currency—including painter Yasuo Kuniyoshi, who was active in the early- to mid 20th century and the subject of a retrospective at the Smithsonian

American Art Museum in 2015.

By bringing together such a broad, adventurous swath of artists and questioning their relationship to each other, Outliers casts even well-known artworks in a new light.

The provocative posturing photographer Cindy Sherman’s Untitled Film Stills (1977-79) takes on added resonance alongside Eugene von Bruenchenhein’s adoring, erotic photographs of his wife Marie, done in the 1940s, and Lee Godie’s photo-booth self-portraits of the 1970s.

The vivid narrative that unfolds in Kara Walker’s print portfolio Harper’s Pictorial History of the Civil War (Annotated) (2005) is deepened by its proximity to works like Sam Doyle’s painting of Abraham Lincoln’s supposed visit to Doyle’s South Carolina home town.

And a robust visual dialogue unfolds among the abstract canvases of Mary Heilmann and Howardena Pindell and the abstract quilts by self-taught artists Annie Mae Young, and Mary Lee Bendolph of Gee’s Bend, Alabama. And West Coast quilt artist Rosie Lee Tompkins.

Some curators would argue that no difference exists between self-taught and trained artists, Ms. Cooke said, but she believes that those distinctions can and should be acknowledged. Within the show’s inclusive, questioning panorama, she added, “difference doesn’t have to read as deficit.”

- Susan Delson

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