In the late 1930s, de Kooning began to paint figures and abstracted interiors with a new liberation in the means of their making, placing himself in opposition to the geometric abstraction then popular in New York. He produced beautifully detailed figurative drawings, modernized figurative paintings (including his only series of paintings of men) where limbs float away from the bodies, and quasi-abstract compositions suggestive of interiors. The works of this period were created through a lengthy revisionary process in which charcoal drawing and oil paint were applied alternatively, and the changes were allowed to show.

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1938
Self-portrait with Imaginary Brother
1939
Seated Man
1940
Seated Woman
1941
Portrait of Elaine
Seated Man (Clown)
1943
Summer Couch
Seated Figure (Classic Male)
1944
The Wave
Woman Sitting