Over the course of his career, Alfred Stieglitz made portraits of artists he befriended and admired, including this photograph of the painter Marsden Hartley (1877–1943). They had first met in 1909, and Stieglitz helped Hartley procure funding for his first study trip to Europe from 1912 to 1915 and even provided him with a stipend for a time. Stieglitz made this monumental and haunting portrait of Hartley the same year that he exhibited approximately 40 of Hartley’s recent Berlin paintings at the gallery known as 291, after its Fifth Avenue address. In 1916 Stieglitz met the artist Georgia O’Keeffe (1887–1986) and organized the first solo show of her work at 291 the following year. He took this sensitive photograph of O’Keeffe creating a watercolor outdoors a short time after the two had embarked on their long and intense relationship. Over the next two decades, Stieglitz created nearly 300 portraits of O’Keeffe, ranging from close-ups of her body to full-figure shots.