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Skull and desert motifs

In 1933 and 1934, O'Keeffe recuperated in Bermuda and returned to New Mexico in 1934. In August 1934, she moved to Ghost Ranch, north of Abiquiú. In 1940, she moved into a house on the ranch property. The varicolored cliffs surrounding the ranch inspired some of her most famous landscapes. Between 1934 and 1936, she completed a series of landscape paintings inspired by the New Mexico desert, often with prominent depictions of animal skulls, including Ram’s Head with Hollyhock (1935) and Deer's Head with Pedernal (1936) as well as Summer Days (1936). In 1936, she completed what would become one of her best-known paintings, Summer Days. It depicts a desert scene with a deer skull with vibrant wildflowers. Resembling Ram's Head with Hollyhock, it depicted the skull floating above the horizon.

In 1938, the advertising agency N. W. Ayer & Son approached O'Keeffe about creating two paintings for the Hawaiian Pineapple Company (now Dole Food Company) to use in advertising. Other artists who produced paintings of Hawaii for the Hawaiian Pineapple Company's advertising include Lloyd Sexton, Jr., Millard Sheets, Yasuo Kuniyoshi, Isamu Noguchi, and Miguel Covarrubias. The offer came at a critical time in O'Keeffe's life: she was 51, and her career seemed to be stalling (critics were calling her focus on New Mexico limited, and branding her desert images "a kind of mass production").

She arrived in Honolulu on February 8, 1939, aboard the SS Lurline and spent nine weeks in Oahu, Maui, Kauai, and the island of Hawaii. By far the most productive and vivid period was on Maui, where she was given complete freedom to explore and paint. She painted flowers, landscapes, and traditional Hawaiian fishhooks. Back in New York, O'Keeffe completed a series of 20 sensual, verdant paintings. However, she did not paint the requested pineapple until the Hawaiian Pineapple Company sent a plant to her New York studio.

During the 1940s, O'Keeffe had two one-woman retrospectives, the first at the Art Institute of Chicago (1943). Her second was in 1946, when she was the first woman artist to have a retrospective at the Museum of Modern Art (MoMA) in Manhattan. The Whitney Museum began an effort to create the first catalogue of her work in the mid-1940s.