He was pretty experimental as he tried his hand in silver-work and even stained glass. He subsequently immersed himself in painting alone and came up with some of the great images of all time, including the Daughters of Revolution, Woman with Plants, The American Gothic, the most prominent among others. The Perfectionist is a painting Wood did in 1936 to illustrate Carol Kennicott, a character from Sinclair Lewis's novel, The Main Street. Lewis Sinclair, a one-time Nobel Laureate for literature, was very keen at recording the culture of small-town America. He perfected this by joining hands with Grant wood, who was also very passionate about his origins and made eight other illustrations of small-town Minnesota.

Carol Kennicott, the central figure in The Mainstream, is orphaned in her teens; she is lucky enough to get an education and goes to college. She, later on, joined a Library school in Chicago and later on graduated to become a librarian in Minnesota. As fate would have it, she falls in love and marries Will Kennicott, a doctor with whom they move to Gopher Prairie. Carol is well-read and seeks to transform this small village into what she thinks is a progressive and more sophisticated community. She is later on frustrated because her efforts bear no fruit as the people there are pretty rigid to change. She moves out of Gopher to Minnesota but comes back.

Here, Wood describes her as a perfectionist, satirical as she gazes quizzically through the organza window. She wonders as the small village is unable to meet her ideal. Wood portrays this interesting character on canvas with oil and canvas. He perfectly blends the 65 by 50cm piece with captivating hues of brown and grey and the patterns. Wood, together with Thomas Hart Benton and John Stuart, embraced regionalism, and he uses that technique in this illustration. Grant Wood is intentional about detail, and this time, he left one of Carol Kennett's buttons halfway done. The unfastening button satirically represents her perfectionist nature; she could not achieve perfection herself. He portrays her as "...a lady who strives for sophistication and elegance but perceives her tiny town as lacking". The Perfectionist is currently on display in the Museum of Fine Arts in San Francisco.