The 100 best paintings in New York: 30-21

Where can I see it?: Museum of Modern Art

Picasso’s women, Hollywood starlets and goddesses from ancient cultures have been given credit for inspiring AbEx giant Willem de Kooning’s timeless, fraught evocation of womanhood. Motherly yet monstrous, she’s prompted volumes of critical response both positive and negative. De Kooning himself struggled so much with the painting that he took it out of his studio—and only reconsidered it in light of praise by critic Meyer Schapiro.—Merrily Kerr

Photograph: Courtesy the Museum of Modern Art, NY. © 2015 The Willem de Kooning Foundation / Artists Rights Society (ARS), New York

Where can I see it?: Brooklyn Museum

A sign painter–turned–Quaker minister and artist, Edward Hicks painted dozens of versions of this iconic celebration of peaceful coexistence. Inspired by a Biblical passage foretelling a time when the wolf, the lamb, the leopard and the goat will live in harmony, Hicks extended the détente to Native Americans and settlers with a version of William Penn making a treaty in the background. Hicks’s pop-eyed lion and leopard don’t look convinced by the new order, but the artist’s folk-art style and hopeful ideology charm, nevertheless.—Merrily Kerr

Artwork: Courtesy Brooklyn Museum

Where can I see it?: Museum of Modern Art

Born Ivan Dombrowski in Ukraine, Graham was a key figure in the New York art world in the years leading up to the emergence of both Abstract Expressionism and NYC’s status as the art capital of the world. Two Sisters is undoubtedly his masterpiece, an odd amalgam of classical and modern. There are echoes of Picasso and Matisse in the work, along with premonitions of AbEx in a flurry of blue brushstrokes between the sitters, which seems to have wandered in from another painting. Strangest of all are the cross-eyed expressions worn by the sisters, a motif Graham often employed.—Howard Halle

Artwork: Courtesy Brooklyn Museum; Dick S. Ramsay Fund

Where can I see it?: The Metropolitan Museum of Art

Although his bold color and friendships linked him to the Impressionists, Pierre Bonnard painted indoors, away from direct observation of nature and open to the transformative effects of his imagination. The orange-hued terrace floor that seems to rise up and purple-toned tree trunk that rests on the surface of the canvas disrupt space, both exciting and soothing the senses with simultaneously vibrant and cool colors.—Merrily Kerr

Photograph: Courtesy the Metropolitan Museum of Art; Rogers Fund; 1956

Where can I see it?: The Metropolitan Museum of Art

Look closely at Jan van Eyck’s exquisitely detailed devotional painting and you’ll see yourself standing witness, or so the tiny reflection on a shiny copper shield on the backside of a Roman solider suggests. A solitary man in a blue turban meets our gaze and seems to ask, “Where do you want to be?” This masterpiece of Northern Renaissance realism lays down the starkest of choices: an orderly choir of worshipers above, or a hideous assortment of ghouls and suffering damned below.—Merrily Kerr

Photograph: Courtesy the Metropolitan Museum of Art; Fletcher Fund; 1933

Where can I see it?: The Metropolitan Museum of Art

All heaven breaks loose in El Greco’s dramatic rendering of John’s revelation as tumbling putti deliver robes to saints slain for their faith. Never more relevant than now, when passive and active martyrdom is front-page news, the painting’s expressive distortions, vivid color and roiling skies forgo the idea of peace in the next life. Inspiration to Picasso (who riffed on it in his famous brothel scene, Les Demoiselles) and 20th-century modernists, the work still offers a blast of visionary discomfort.—Merrily Kerr

Photograph: Courtesy the Metropolitan Museum of Art; Rogers Fund; 1956

Where can I see it?: The Cloisters

Our notions about kids needing to be, you know, kids are fairly recent; they were once seen as tiny adults. Goya straddles the line in this portrait of the young son of an aristocratic banking family, who is winsomely adorbs but stiff as a little doll in his terrific red jumpsuit. (All children should wear a lace-edged silk sash!) His pets carry symbolic weight, bookending him between the innocence of caged finches and the rapaciousness of the cats who hungrily eye the magpie he holds on a leash. The artist must have known how beloved Manuel would become, as he signed the work on the calling card in the magpie’s beak.—Joseph Wolin

Photograph: Courtesy the Metropolitan Museum of Art; Rogers Fund; 1956

Where can I see it?: Brooklyn Museum

Borrowing from 19th- and 20th-century Western art, African-American artist Mickalene Thomas adapts pictoral tropes to bold, rhinestone-encrusted enamel-and-acrylic depiction of luxe interiors and colorful landscapes in this portrayal of Claude Monet’s house, where Mickalene resided in 2011.—Anne Doran

Photograph: Courtesy Brooklyn Museum, A. Augustus Healy Fund, 2012.73a-b. © Mickalene Thomas. Courtesy Lehmann Maupin Gallery, New York and Hong Kong

Where can I see it?: Brooklyn Museum

In his celebratory portraits of ordinary black men and women, Kehinde Wiley redresses a Western cultural history that does not acknowledge their experience. His subjects—generally strangers encountered on the street—are depicted in poses they’ve chosen from Old Masters paintings, typically against ornate backgrounds. Here Wiley appropriates Jacques Louis David’s Bonaparte Crossing the Alps at Grand-Saint-Bernard (1800–01), substituting the figure of Napoleon for one of a man in camouflage and Timberlands.—Anne Doran

Photograph: Courtesy Brooklyn Museum, Collection of Suzi and Andrew B. Cohen , L2005.6. © Kehinde Wiley. Courtesy Sean Kelly Gallery, New York

Where can I see it?: Museum of Modern Art

By pouring Day-Glo pigments mixed with latex on the floor to make this sculpture, the solidity of traditional pictures appears to melt. Instead of using liquid to make an image, Benglis allowed the medium to become a record of its own flowing impulse. The skinlike puddle and its flattened biomorphic shape and oozing nature add a bodily reference to an artwork that’s already a hybrid of Modernist abstraction, Pop Art and Minimalism.—Jennifer Coates

Photograph: Courtesy the Museum of Modern Art, NY. Gift of the Fuhrman Family Foundation through the Modern Women's Fund