Guare's The House of Blue Leaves, his most renowned work prior to Six Degrees of Separation, presents the author's darkly comedic perspective on contemporary America. This farce centers on a working-class zookeeper from Queens who, having failed as a songwriter, vents his frustrations on his mentally ill wife.

Theodore Dreiser's An American Tragedy (1925) narrates the tale of a young man who adopts the guise of a well-bred gentleman to win over a society girl. In his efforts to conceal his true background, Clyde Griffiths becomes entangled in a murder.

Tom Wolfe's novel The Bonfire of the Vanities (1987) offers a biting critique of affluent New Yorkers who possess every material luxury but lack genuine values or purpose. The protagonist, a wealthy bonds trader, finds his life unraveling when he is implicated in the hit-and-run death of a young African-American man from Harlem.

Richard Wright's Native Son (1940) revolves around Bigger Thomas, a young African-American man employed by a liberal, affluent Northern family. Although the family encourages him to engage in social activities, one night, fearing accusations of improper conduct, he accidentally kills their daughter. In prison, he concludes that violence is the only alternative to submission in a white-dominated society.

George Bernard Shaw's play Pygmalion (1914), the author's most humorous and beloved work, recounts the story of Henry Higgins, who, on a bet, transforms a Cockney flower girl into someone who can pass for a duchess. The play explores the English class system as Eliza Doolittle, having completed her transformation, finds herself belonging to neither the upper nor the lower class.