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The 100 Greatest New York City Artworks, Ranked

When the artist Florine Stettheimer returned from a sojourn in Europe during the 1910s, she vowed to paint New York City as she saw it. She wrote a poem in which she spoke of a place where “skytowers had begun to grow / And front stoop houses started to go / And life became quite different / And it was as tho’ someone had planted seeds / And people sprouted like common weeds / And seemed unaware of accepted things.” She continued on, concluding ultimately that “what I should like is to paint this thing.”

She did so, producing works such as New York/Liberty (1918–19), in which downtown Manhattan’s busy port is shown with a chunky Statue of Liberty welcoming a ship. It’s a bombastic vision of all that New York has to offer, and it’s one of the works that make this list, which collects 100 of the best pieces about the city.

The works ranked below take many forms—painting, sculpture, photography, film, performance, even artist-run organizations whose activities barely resemble art. They pay homage to aspects of New York life across all five of its boroughs. Secret histories are made visible, the stuff of everyday life is repurposed as art, and tragic events from New York lore are memorialized. Binding all of these works is one larger question: What really makes a city?

These 100 works come up with many different answers to that query, not the least because a significant number of them are made by people who were born outside New York City.

Below, the 100 greatest works about New York City.

25: David Wojnarowicz, “Arthur Rimbaud in New York,” 1978–79

Arthur Rimbaud was a 19th-century French writer who famously had a relationship with the poet Paul Verlaine. A little under a century after Rimbaud’s death, another queer artist in another country, the New Yorker David Wojnarowicz, donned a mask of the writer’s face and wore it around the city. Wojnarowicz photographed the results for a series called “Arthur Rimbaud in New York,” which is now celebrated as one of the great works in the canon of queer art.

In taking on Rimbaud’s guise, Wojnarowicz suggested that the tragic conditions of Rimbaud’s life—the poet’s relationship with Verlaine turned ugly, and even violent—were not all that dissimilar to his own. In these pictures, Wojnarowicz ventures out to areas in New York that he knew well, including the piers, where he and other gay men cruised, and shoots himself looking out of place. The Rimbaud mask does not seamlessly fit over Wojnarowicz’s face, and it is difficult to know what emotions are passing through the artist because his expression is kept concealed. The effect is off-putting, with the city where Wojnarowicz was based acting not as a home but as an inhospitable backdrop.

12: Martin Wong, Big Heat, 1986

Martin Wong made no secret of the fact that he was erotically fascinated by firemen. “I really like the way firemen smell when they get off work,” he once wrote. “It’s like hickory smoked rubber and B.O.” In this painting, two of them kiss before a partially charred building—a symbol, perhaps, of their fiery desire.

The Whitney Museum, the institution that owns this work, has pointed out that the building looks a lot like the tenements of the Lower East Side, where Wong lived. While rendering a structure that could be found in the real world, even building out the paint slightly to more closely suggest rough-hewn bricks, Wong casts the scene in dreamy darkness that makes clear this is a fantasy. The friction between reality and fiction—the graffiti on the bricks versus the lack of buildings around this one—is an example of how Wong’s Manhattan is neither entirely our New York nor the one he dreamed up.