The 20th-century painting collection is rich in number (over 400) and variety. There are 186 paintings by American artists, 170 by Europeans, and eleven by Latin American artists. Among the Europeans, French and Italian artists working in the 1950s are best represented, as is the CoBrA movement (see Hollaender Collection). There are also 84 examples of Soviet Socialist Realism (see Davies Collection). The Schoolboy by Albert Gleizes is the first cubist painting to enter the collection.

American holdings include works by such important early 20th century figures as George Bellows, John Sloan, and John Steuart Curry who was artist in residence at the UW from 1936 until his death in 1946. Also included are paintings by Adolf Gottlieb, Fritz Glarner, Hans Hofmann, Jack Tworkov, Mark Rothko, Sam Gilliam, Helen Frankenthaler, Al Held, Robert Cumming, and Gronk.

Works by Chicago Imagists and a selection of the so-called magic or psychological realists who flourished in Wisconsin immediately following WWII represent the painting of the Midwest.

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