Year: 1925

Medium: Oil on canvas

The Bootleggers is a 1925 painting by American realist Edward Hopper. The work generally marks the end of his early period before painting the House by the Railroad that same year, the start of his mature or classic period. The painting depicts a nautical scene in a subdued blue and gray palette, showing three men on board a motorboat staring at the shore where another man, standing besides a large house, stares back at them. It has been described and interpreted as Hopper's most overt, political, and even contrarian work.

Art historians and critics believe that the painting is loosely based on the history of rum-running during Prohibition (1920–1933). The scene is thought to depict the smuggling of alcohol along the coast of Gloucester, Massachusetts, but Hopper's art dealer made it known that the painting was not based on an actual location but on several different scenes blended together. The Bootleggers was first exhibited in November at the Brooklyn Museum, followed by several other showings. Hopper held on to the painting for almost three decades until the Currier Museum of Art acquired it for their collection in 1956.

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