Childe Hassam, Flags, Fifth Avenue, 1917
This scene of Fifth Avenue by American Impressionist Childe Hassam was one of 30 such images showing the flag-bedecked thoroughfare during World War I. The canvas captures the dynamic verve of New York just as the country began its ascent to superpower status. Bequeathed to the Metropolitan Museum of Art by its former owner, Brooke Astor, the work disappeared in 2002 when her son wrongfully sold it to private hands for $10 million. Its whereabouts remain unknown, even though it’s one of the most famous American paintings of the early 20th century.
George Bellows, The Lone Tenement, 1909
This poignant image of the last remaining building from a neighborhood razed to make way for the Queensboro Bridge (which opened the same year the painting was completed) speaks to the constant churning of New York, where nothing stays the same for very long.
Hugh Ferriss, Maximum Mass Permitted by the 1916 New York Zoning Law #4
Ferriss was a trained architect who spent his career rendering views of building projects. This charcoal study is one of several illustrating the building limits permitted under the first city law regulating skyscraper construction. Although it is a technical drawing of an imaginary edifice, Ferriss’s powerful handling elevates the subject into an emblem of New York ambition.
John Sloan, Sixth Avenue Elevated at Third Street, 1928
Sloan, a member of the Ashcan School of urban realists, once noted, “The fun of being a New York painter…is that landmarks are torn down so rapidly that your canvases become historical records almost before the paint on them is dry.” That’s certainly true of this depiction of the el that once ran from West 59th Street in midtown to Rector Street in lower Manhattan. The scene is a veritable time capsule of life in Jazz Age New York, showing trains trundling overhead as a group of young women head out for an evening on the town. In the background on the right, one can see the distinctive tower of the Jefferson Market Library, which still stands today.
Georgia O'keeffe, Pink Dish and Green Leaves, 1928
Georgia O’Keeffe’s art is synonymous with New Mexico, but between 1907, when she first came to New York to study at the Art Students League, and 1949, when her husband, Alfred Stieglitz, died, she called the city home. Gotham’s skyline became a focus in her work during the 1920s, a time when, according to the artist, “buildings sometimes seemed to be going up overnight.” She painted several views of the East River from the upper floors of the Shelton Hotel on Lexington Avenue and 49th Street, where she lived. This still life juxtaposes the stolid geometry of a nearby tower with the soft contours of leaves poking out of a glass dish, foreshadowing the botanical compositions that would become O’Keeffe’s signature work.
Charles Demuth, I Saw the Figure 5 in Gold, 1928
Demuth was a pioneer of the Precisionist style, but in this work he anticipates Pop Art by more than 30 years. The piece is inspired by a poem by his friend William Carlos Williams, in which the author describes a fire truck racing past him one night in Manhattan. Demuth melds the truck (represented by its engine number), Williams’s name and the surrounding street into a hallucinatory vision of the city and its sounds.
Georgia O'keeffe, Radiator Building, Night New York, 1927
In this skyscraper study by O’Keeffe, the building is composed as the sort of central, abstracted form that became a feature of her work. The painting depicts the former headquarters of the American Standard company, now the home of the Bryant Park Hotel.
Reginald Marsh, Why Not Use the “L”?, 1930
A master of the urban character study, Marsh uses the blank expression of a seated woman and the slumped posture of a sleeping man to distill the economic despair of Depression-era Gotham into this subway scene. The painting’s title comes from the sign hung just above them, which extols the comfort of the elevated train lines that would soon begin to disappear from the city.
Paul Cadmus, Coney Island, 1934
Cadmus slyly employed the conventions of classical figure painting to satirically subversive ends. He never hid the fact that he was gay, and often infused his work with a bawdy homoeroticism, even when the subject was ostensibly heterosexual, as in this expansive view of working-class revelers at the beach.
Joseph Stella, The Brooklyn Bridge: Variation on an Old Theme, 1939
Stella painted six views of the Brooklyn Bridge; this one, perhaps the best known, shows the view toward Manhattan through the bridge’s Gothic arches and suspension cables. It’s a religious icon, a stained-glass window on canvas for some imagined church of New York and its indomitable energy.
Piet Mondrian, Broadway Boogie Woogie, 1942-43
Like many European modernists, Dutch painter Piet Mondrian fled the Continent in 1938 as war clouds began to gather, settling first in London before moving to New York in 1940, where he remained until his death four years later. Although clearly abstract, Broadway Boogie Woogie is a kind of portrait of the artist’s adopted home, an homage to both New York’s street grid and the syncopated rhythms of his favorite kind of music: jazz.
Edward Hopper, Nighthawks, 1942
Hopper’s noir masterpiece is a timeless study of being alone together. The illuminated, glass-enclosed interior of a downtown diner contrasts starkly with the street outside, evoking city life as a fishbowl filled with people who are unaware of one another, yet still share an odd state of grace.
George Tooker, The Subway, 1950
This painting is Tooker’s best known, and its nightmarish depiction of straphangers moving somnambulantly through tiled hallways crackles with Cold War paranoia.
Andy Warhol, A Boy for Meg, 1962
Andy Warhol began his artistic career by hand-painting his pop-culture artifacts and icons, and this depiction of the front page of the New York Post from 1961 is exemplary of that early style. A celebration of the city’s tabloid culture, the work is also a nascent expression of celebrity worship that would become Warhol’s signature theme.
Alex Katz, Cocktail Party, 1965
Midcentury Gotham is smoothly captured by Pop-figurative painter Alex Katz in this scene straight out of Mad Men.
Romare Bearden, Uptown Looking Downtown, 1965
City life as seen from Harlem is the subject of this collage by the great African-American artist Romare Bearden, who combines elements of Pop Art and cubism to give this work its sense of jangling dynamism.
Red Grooms, The Subway from Ruckus Manhattan, 1976
Anything can happen on the subway, of course, but things get downright funky in Grooms’s rendition of a subway train as a life-size, three-dimensional cartoon. The original installation of the piece permitted viewers to actually stroll through the car.
Jane Dickson, Hotel Girl, 1983
Depending on your point of view, Gotham during the 1980s was either hell on earth or the coolest place on the planet. This neon-soaked pastel by artist Jane Dickson offers evidence for both, depicting the city as a sort of glamorous inferno. Dickson’s studio at the time was near Times Square, the epicenter of crime and grime in New York back then.
Martin Wong, Stanton Near Forsyth Street, 1983
The Lower East Side before gentrification is the subject of this street scene featuring vacant lots and burned-out tenement buildings. Artist Martin Wong had moved to New York City from San Francisco in 1978, settling on the LES and making the neighborhood, which was largely Hispanic at the time, a focus of his work. In the painting, he appears on the left, while his frequent collaborator and lover, Miguel Piñero, the Nuyorican poet and playwright, can be seen on the right. The top half of the composition features stylized outlines of hands forming words in American Sign Language, a frequent motif in Wong’s compositions.
Robert Longo, Master Jazz, 1982
This mixed-media piece by “Pictures” Generation artist Robert Longo is really more about the references it makes to cinematic conventions than about Gotham. But the inclusion of a sculptural relief of the top of the Empire State Building suggests an establishing shot for a New York story of some sort, or maybe some notion that living here feels like being in a movie. Whether what we’re seeing represents, for example, the dream or nightmare of the sleeping woman on the far right (modeled by the late artist Gretchen Bender) is hard to say, though the face of the screaming man belongs to noted choreographer Bill T. Jones.
Robert Moskowitz, Syscraper, 1995
Beginning in the 1970s, Robert Moskowitz created several starkly minimalistic renderings of the Twin Towers—like this one, whose sense of foreboding in retrospect seems eerily prescient of 9/11.
Alex Katz, City Night, 1998
The play of grays in this view of lit apartment windows through bare tree branches transforms a familiar New York winter sight nto brooding visual poetry.
Gerhard Richter, September, 2005
The famed German painter based this image on a photo of the 9/11 attacks, and while the main thrust of this work speaks generally to the sometimes complicated relationship between historical events and their photographic representation, it also depict perhaps the most infamous and indelible moment in New York’s history.
Elizabeth Peyton, West 11th Street, Greenwich Avenue, and 7th Avenue, New York City, 2008
Peyton is better known for her intimate portraits of young and beautiful subjects (most of them male), so this Greenwich Village scene is somewhat uncharacteristic of her work. It does, however, crystallize something about millennial New York—its anodyne sheen, perhaps, but also its most salient quality: a continuous sense of renewal, made possible by an ability to attract successive generations of fresh, ambitious talent from all over the world.