In 1937, Grant Wood was asked to illustrate a novel that, like his painting American Gothic, had already become a classic: Sinclair Lewis s Main Street. Published nearly twenty years earlier in 1920, Lewis s novel had come to represent the Midwest just as Wood s paintings symbolized that region during the 1930s. Today Sinclair Lewis and Grant Wood still endure as cultural figures who captured something distinctive yet elusive about the Heartland; yet Lewis and Wood looked at the American Midwest through different eyes. Lewis saw provincialism and narrowness, while Wood gloried in the solid, earthy strength of his fellow midwesterners and their land. Both men felt conflicted about their homes, and these dichotomies filtered into their work. This publication explores the American Main Street of both Lewis and Wood through the nine drawings Wood created for the 1937 Special Editions Club book, Main Street, as well as two self-portraits of the artist as a Midwesterner.