If things had gone differently, Georgia O’Keeffe would be famous for her paintings of skyscrapers, not her pictures of flowers. Starting in 1925, she began painting tall, monolith-like structures in cities devoid of people and cars. Thee strange, entrancing pictures capture a New York remade by modernity—and act as some of the most crucial documents of that transformation. What a shame it is that these canvases do not act as her calling card.
For that, we have O’Keeffe’s husband, the artist Alfred Stieglitz, to thank. O’Keeffe wanted to hang her paintings of skyscrapers—“my New Yorks,” she called them—in a 1925 group show at Stieglitz’s Intimate Gallery. He shot that idea down, and instead pushed her to present her landscapes, which contain few of the sharp, hard forms seen in the New York paintings. But O’Keeffe knew she was onto something, and she was vindicated the next year, when she succeeded in exhibiting one of her New Yorks. It sold for $6,000, hardly anything to sneeze at during her day.
Nearly a century on, O’Keeffe posthumously proves Stieglitz wrong all over again in the form of “Georgia O’Keeffe: ‘My New Yorks,’” an entire exhibition about these paintings that is now in its final days at the Art Institute of Chicago. (It will soon travel to Atlanta’s High Museum of Art, where it opens in October.) The show reveals a strong connection between her New Yorks and her landscapes, and in that way, it suggests that working across the two modes put O’Keeffe on the path toward painting the jimsonweeds and cannas for which she is so well known.
I approached the Chicago show dubious of this concept, worried that this was convenient art-historical rewriting in service of attention-grabbing curation. O’Keeffe had painted landscapes before she even called New York her main home. Could it really be that a five-year burst of creativity—the short period lasting from 1924 to 1929 when she most frequently painted Manhattan—put her on a new course? Well, consider this an apology to the exhibition’s organizers, Sarah Kelly Oehler and Annelise K. Madsen, who have marshaled a good deal of objective proof that O’Keeffe’s landscapes owe plenty to her New Yorks.
Oehler and Madsen point, for example, to O’Keeffe’s 1930 show at Stieglitz’s An American Place gallery, for which she allowed her cityscapes and landscapes to rub shoulders. New York, Night (1928–29), a long, thin painting in which lit-up windows illuminate an inky sky, was exhibited beside After a Walk Back of Mabel’s (1929), in which the tip of a tall, jagged rock pushes against blazing planes of blue and red.

The Art Institute of Chicago show reunites the two works, and the similarities between the modernist tower and the Southwestern formation are surprising. Both emphasize verticality, with their respective subjects seeming tall, foreboding, and awesome in equal measure. Both are experiments in light—the former considering how a profusion of illuminated rooms and cars had reshaped the Manhattan sky, the latter mulling how a gigantic boulder can turn a sunny landscape dark. New York, Night is the more naturalistic of the two, but it seems twinned with its more abstract counterpart, which depicts a space far beyond the Big Apple. Without O’Keeffe’s New Yorks, there is no O’Keeffe as we now understand her.
An itinerant O’Keeffe first moved to New York in 1907, long before she ever met Stieglitz, but her relationship with him led her to more firmly put down roots in the city starting in 1918. Yet for the six years that followed, she remained more focused on abstraction, painting ripples of color that sometimes coalesced to form lakes, mountains, and flowers.
Everything changed in 1924, the year she moved into the Shelton, a Midtown mega-hotel. In O’Keeffe’s recounting, the accommodations weren’t extraordinary—“the bedroom is tiny,” she wrote to her sister Ida—but the views were worth every penny. She could pause painting to gaze down at the taxi cabs and businessmen far below, and find much to admire. They lived in rooms on the 11th and 28th floors before ending up on the 30th floor, where they were so high up that Stieglitz said he felt as though he were “at mid-ocean,” referring to how quiet it was.
Most American modernists were scrappier, toiling away in studios closer to the ground, far beyond Manhattan’s busiest streets. O’Keeffe knew the arrangement was a bit odd, but she felt it challenged her to work differently, for the high-up views were exactly what the “the artist of today needs for stimulus,” as she once put it.

That stimulus led O’Keeffe almost immediately to try her hand at something new. New York Street with Moon (1925), one of the oldest representations of New York by O’Keeffe in the Chicago show, is a notable departure from other works of the same time period. The wavy, sinuous forms that appear in O’Keeffe’s contemporaneous abstractions are confined only to the sky here, where rows of clouds threaten to cover the moon. Down below, the buildings are harsh, all unevenly situated rectangles of brown. A blindingly bright streetlight overwhelms the composition, casting an oversized halo of white around its bulb.
O’Keeffe’s non-figurative work from this era contains a sense of harmony. New York Street with Moon, by contrast, is jagged, the kind of painting one’s eye stumbles over while trying take it in. Her New Yorks, it would seem, introduced an awkwardness that wound its way into her abstractions.
With City Night (1926), O’Keeffe starkened Manhattan even more, making it appear like rows of windowless towers that loom above one’s head. Save for a slice of deep blue sky visible between them, all that can be seen are blacks, whites, and greys. The Chicago curators make a strong case that this painting bears some relation to two completely non-objective works, both centered around similar tones, in which an obelisk-like white shape protrudes into a void. These are stony, foreboding images that are nowhere near as sensuous as her previous abstractions.

All this aesthetic severity was more than artistic choice. Today, there are more than 400 skyscrapers in New York, but there were not nearly so many during O’Keeffe’s day. When she took up residence in the Shelton Hotel, there wasn’t much else around her of the same height. (Consider her paintings of the East River as seen from the hotel, in which one can see smokestacks in Long Island City and the rollicking hills far beyond them. Good luck finding such a view from Lexington Avenue today.) Neither the Empire State Building nor the Chrysler Building had been completed yet, and most else around the Shelton looked tiny by comparison. The building she called home, then, was a big interruption in a flatter landscape, so her art had to capture that quality.
For O’Keeffe, the Shelton was a sublime object, commanding both fear and veneration. Perhaps she borrowed that quality for it for the 1929 oddity Black Cross, New Mexico (1929), in which a cruciform covers up part of a lush sunset and obstructs a clean view of the ovular mountains below. The cross here is pushed close to the viewer and made confrontational, rendered in a way that recalls the frontality O’Keeffe afforded to her skyscrapers.

The year O’Keeffe painted that work, everything changed all over again. She took up residence in New Mexico, and that state became her primary home. Even though she continued painting New York, the city no longer looked the same in her eyes: Manhattan (1932) renders a multitude of skyscrapers, one on top of the other, in shades of pink, white, and grey, with fresh flowers peeking out from these structures. Conjure a Manhattan street, and the only place you are likely to find pink is in the spat-out bubblegum beaten into a sidewalk. Here, however, O’Keeffe’s rose tones look right at home.
Some people soften with age. Others, like O’Keeffe, soften with place. But although you could take O’Keeffe out of New York, you could not take New York out of O’Keeffe. In 1970, 21 years after leaving New York for good, she returned to her 1926 canvas City Night and repainted it. The night sky seen between the gargantuan buildings is a brighter shade of blue; glimmers of light between the buildings are more apparent. O’Keeffe has added four twinkling stars. Maybe she meant to indicate that New York remained her North Star, even when she was far away from the city.