Guare's The House of Blue Leaves, his most well-known work before Six Degrees of Separation, contains the author's darkly humorous vision of modern America. This farce features a working-class Queens zookeeper who fails as a songwriter and takes out his frustration on his insane wife.

Theodore Dreiser's An American Tragedy (1925) tells the story of a young man who, to win a society girl, takes on the persona of a well-bred young man. In his attempt to hide the truth about his past, Clyde Griffiths finds himself involved in murder.

Tom Wolfe's novel The Bonfire of the Vanities (1987) is a scathing portrayal of wealthy New Yorkers who have all the material comforts they could desire but lack any true values or meaning in their lives. Wolfe's protagonist is a rich bonds trader who finds his whole world coming into question when he is implicated in the hit-and-run death of a young African-American man from Harlem.

Native Son (1940), by Richard Wright concerns Bigger Thomas, a young African-American man hired by a liberal, wealthy Northern family. The family encourages him to participate in social events, but one night, afraid that he will be accused of improper actions, he accidentally kills the daughter. In prison, he reaches the conclusion that violence is the only alternative to submission in white society

George Bernard Shaw's play Pygmalion (1914), the author's funniest and most popular play, tells the story of Henry Higgins, who on a bet transforms a Cockney flower-seller into being able to pass for a duchess. The play delves into the English class system as Eliza Doolittle, having successfully completed her lessons, ends up belonging to neither the upper class nor the lower class.