The 100 best paintings in New York: Solomon R. Guggenheim Museum

Rank: 87

No one with any assurance can point to the first truly abstract painting in art history, but this one comes pretty close. It is, oddly, the result of deliberately slow product rollout, at least according to the Guggenheim. It turns out that well before he created this canvas, Kandinsky knew precisely where he wanted to go with respect to abstract, or non-objective, art, but he was concerned with public reaction. So in the paintings leading up to this one, he maintained tenuous connections to representation, before finally dispensing with them altogether here.—Howard Halle 

Photograph: Kristopher McKay

Rank: 72

This image from Picasso’s blue period—named for both the color and the mood of his work—shows a favorite subject of the time, the downtrodden worker. She appears nearly weightless in a lengthened Mannerist style, and stylized in a way that hints at the artist’s later experiments with abstraction.—Heather Corcoran

Solomon R. Guggenheim Museum, New York, Thannhauser Collection, Gift, Justin K. Thannhauser © 2012 Estate of Pablo Picasso/Artists Rights Society (ARS), New York Photo: Kristopher McKay © The Solomon R. Guggenheim Foundation, New York

Rank: 71

Picasso was fond of depicting Marie-Thérèse Walter while she slept, because he thought it captured her in her most vulnerable, intimate state. Here, she lays her head on an arm that looks like a fleshy, sensual extension of her flaxen locks.—Howard Halle

Solomon R. Guggenheim Museum, New York, Thannhauser Collection, Gift, Justin K. Thannhauser 78.2514 © 2007 Estate of Pablo Picasso/Artists Rights Society (ARS), New York

Rank: 63

While not as radical as Malevich’s later Suprematist compositions (like Black Square), Morning in the Village is arguably the most beautiful and sublime of the vaunted Russian avant-gardist’s works. In this timeless scene, a country hamlet stirs itself after a blizzard, its streets and rooftops blanketed by a purifying white that erupts in prismatic shards of blue and red touched with accents of yellow, black and gray. At once formal and hallucinogenic, it rivals the work of Bruegel as a panegyric to peasant life.—Howard Halle

Solomon R. Guggenheim Museum, New York

Rank: 49

In the course of a career-long project to make visible the passage of time, conceptual artist On Kawara sent out telegrams to friends and acquaintances announcing “I am still alive” and postcards recording what time he had gotten up that day. Between 1966 and 2013, a year before his death, Kawara also produced almost 3,000 paintings very like this one, each describing nothing but the date on which it was made.—Anne Doran 

Photo: Courtesy David Zwirner, New York/London