They tried to tell Georgia O’Keeffe that even men struggled painting skyscrapers, and she should probably stick to lady things like flowers.

Nevertheless she persisted and eventually painted City Night, among a series of other cityscapes. After O’Keeffe painted her first skyscraper scene, New York Street with Moon, she asked her husband Alfred Stieglitz if he would include the painting in a show he was putting together at Anderson Gallerie. That’s when he made his snarky comment about how even men struggle to paint skyscrapers and refused to showcase her painting. Annoyed, but not discouraged, O’Keeffe later insisted that New York Street with Moon be displayed during her own show at The Intimate Gallery where it sold for $1,200. Haters gonna hate.

After that, O’Keeffe continued to portray cityscapes and skyscrapers, painting more than 20 scenes of New York between 1925 and 1930. In City Night, O’Keeffe painted the skyscrapers as looming geometric shapes that dwarf even the moon. “One can’t paint New York as it is, but rather as it is felt,” O’Keeffe said, regarding her philosophy for painting the city.

O’Keeffe lived on the 30th floor (back then that was considered suuuuper tall!) of one of New York’s first towers: the Shelton. "I had never lived up so high before and was so excited that I began talking about trying to paint New York,” she once said. At the time, skyscrapers were fairly new and considered symbols of American wealth and power. U-S-A!

But then in 1929, the stock market crashed, and the towers lost some of their appeal. In addition, during the summer of 1929 O’Keeffe traveled to New Mexico for the first time, and started painting cow skulls and other Southwestern-inspired scenes. Thus ended her brief, but wonderful, phase painting the concrete jungle.