The 100 best paintings in New York: 50-41

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

Aristotle with a Bust of Homer is one of the greatest paintings by one the greatest artists in history, and shows the greatest hallmark of Rembrandt’s style: the interplay of light and dark. Then there is Rembrandt’s uncanny ability to evoke the innermost thoughts of his subjects through the play of facial expression, or the fall of light across someone’s features. These qualities are put in the service of a debate, which the artist may be having with himself: What has more value, integrity and the life of the mind, or the material rewards of success? The latter is represented by the gold chain with a medallion featuring Aristotle’s pupil Alexander the Great. It resembles the kind of awards given as an honorarium by a patron to an artist for services rendered. As for the former, it’s symbolized by the bust of Homer on which Aristotle rests his hand—it’s as if by doing so, he can divine an answer to the question.—Howard Halle 

Photograph: Courtesy special contributions and funds given or bequeathed by friends of the Museum

Where can I see it?: Solomon R. Guggenheim Museum

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

Where can I see it?: East 128th Street and Harlem River Drive

New York City graffiti artist Keith Haring (1958–1990) painted this mural at the height of the crack epidemic of the 1980s. It is one of many images by Haring—who died at age 31 of complications of AIDS—that used his pictogramlike drawing style and cast of radiant babies, barking dogs, and dancing figures to draw attention to the political and social causes of his time.—Anne Doran 

Photograph: Courtesy Creative Commons/Flickr/superk8nyc

Where can I see it?: Museum of Modern Art

Both fierce and seductive, this wall sculpture resembles the view from inside a satellite. Bontecou was merely 28 years old when she made this construction, the first in her famed series of wall-mounted steel-and-canvas sculptures. She incorporated soiled canvas from conveyor belts, thrown away from a laundry below the artist’s East Village apartment, and by doing so created a crazy quilt of industrial detritus.—Barbara Pollack 

Photograph: Courtesy the Museum of Modern Art, NY. Gift of Mr. and Mrs. Arnold H. Maremont © 2015 Lee Bontecou

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

Venetian painter Tintoretto turns the story of Christ feeding the masses into a raging party among his city’s wealthy in this large-scale painting. The Bible describes two accounts of Jesus turning a few loaves of bread and a handful of fishes into a banquet, and here, Tintoretto depicts the miracle as told in John 6:1–14. Rather than surrounded by the suffering poor, however, the Savior is flanked by well-heeled fashionistas who could probably benefit from diets. Tintoretto was kind of the Jeff Koons of his day, and this painting, like many of his larger works, was probably finished by his studio assistants rather than the master himself.—Barbara Pollack 

Photograph: Courtesy the Metropolitan Museum of Art; Francis L. Leland Fund

Where can I see it?: Museum of Modern Art

While the image of the Stars and Stripes appears elsewhere in American art, no one transcribed the subject as literally as Johns did here: The canvas is the same shape and size as a typical flag, all but eradicating the distinction between the object and its representation. Of course, that isn’t entirely the case. Created with encaustic (pigment mixed into melted wax), Flag, with its drips and smears seemingly frozen into place, is indubitably painted, and one can easily see a collage of newspaper strips running beneath the colors. Still, it serves as a banner for an artist who fired some of the first shots against Abstract Expressionism, the dominant style at the time, helping to usher in a new era of American art defined by Pop Art and Minimalism.—Howard Halle

Photograph: Courtesy Creative Commons/Flickr/brendanlynch

Where can I see it?: Museum of Modern Art

Gerhard Richter’s five-decades-plus exploration of painting’s continued possibilities has included both abstraction and realist work based on found images. The 15 paintings in this series all derive from photographs of members of the German radical-left terrorist group, the Red Army Faction, three of whom were found dead in their prison cells on, you guessed it, October 18, 1977.—Anne Doran 

Photograph: Courtesy the Museum of Modern Art, NY. The Sidney and Harriet Janis Collection, gift of Philip Johnson, and acquired through the Lillie P. Bliss Bequest (all by exchange); Enid A. Haupt Fund; Nina and Gordon Bunshaft Bequest Fund; and gift of

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

Known more for his brawny depictions of boxing matches, Ashcan School painter George Bellows sometimes turned his attention to the leisure activities of the rich and famous. Here, the annual tennis tournament at the gold coast of Newport, Rhode Island, is his ostensible subject. But, while one player in proper whites reaches high in the air in the foreground, Bellows’s interest is not in the game but in the wealthy fans lingering on the grass, festooned in gowns and carrying parasols. It’s a scene he would have known well. An avid sportsman, recruited by baseball scouts before devoting himself to art, Bellows was something of a whiz with a rackeet.—Barbara Pollack 

Photograph: Courtesy the Metropolitan Museum of Art; Miss Adelaide Milton de Groot

Where can I see it?: Museum of Modern Art

With its implausibly tilted tabletop holding a basket and three apples, this painting shows Matisse’s interest in playing with perspective. Finished in 1916, The Rose Marble Table was noted by Modernist critic Clement Greenberg for its cool, “prost-prismatic” color as opposed to the vibrant “hot” hues of the artist’s earlier Fauvist period.—Heather Corcoran 

Photograph: Courtesy the Museum of Modern Art, NY. Mrs. Simon Guggenheim Fund. © 2015 Succession H. Matisse / Artists Rights Society (ARS), New York

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

This image of the legendary American expat writer represents the young Picasso’s great turn of fortune. From her very first meeting with Picasso, Stein, who came from a wealthy Pennsylvania family of German Jews, was absolutely certain that he was the greatest artist of his age. She saw in him a kindred spirit—a revolutionary figure whose genius was bound to be recognized. More than a likeness of crucial benefactor, Stein’s portrait signals the beginning of Picasso’s transition toward the stylistic breakthrough that would cement his place in art history.—Howard Halle 

Photograph: M.Flynn / Alamy