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Rockwell was commissioned to paint Guiding Influence to promote a nationwide essay contest celebrating the bicentennial of the birth of George Washington, the nation's first president and unfailing patriot. Rockwell chose Jack Parker, a fourteen-year-old high school student, to be his model for Guiding Influence, as Parker seemed to embody the appearance and values of the typical American boy. With his fair skin, white shirt, and clean-cut good looks, Parker projected the great optimism and potential of American youth.
After Rockwell completed Guiding Influence, the United States Congress passed a bill appropriating funds to reproduce five million lithographic posters of the painting which were then distributed in the nation's high schools to promote the essay contest. Later, in 1932, Sears, Roebuck & Co. published the painting on the cover of its spring catalogue with a circulation of 8,500,000.