Topdog/Underdog features just two characters: Lincoln and Booth, African American brothers living in a sparsely furnished apartment without running water in an unnamed city.
Lincoln, often referred to by Booth as “Link,” is the older brother by five years. Link is in his late thirties and used to be married to a woman named Cookie, but she slept with Booth and subsequently the two divorced. He plays the guitar and works as an Abraham Lincoln impersonator. As an impersonator he dresses up in Lincoln attire, including whiteface, and sits quietly in the dark while people pay to come into the “theater” and shoot him with a prop gun. Link used to work on the streets as a successful card hustler, but he quit cold turkey after his close associate, Lonny, was shot and killed. He is the “topdog.”
Booth is the “underdog.” The younger of the two brothers, Booth is unemployed but desperately trying to teach himself three-card monte so that he can be a successful card hustler like his brother. Early on in the play he gives himself the nickname “3-Card” and threatens to shoot anyone who doesn’t call him by his new name, foreshadowing his irrationality and more violent instincts. He has been seeing a woman named Grace off and on for the last two years, and he is largely motivated to earn money so that he can impress her. Though he is not employed, he is the one who rents the apartment and controls its comings and goings.
Link and Booth are the only characters who speak in the play, but there are a handful of other characters who are referenced throughout and who influence the two brothers. Lonny was Link's closest associate when he was hustling cards on the street, but he was shot and killed one afternoon. They never learned who murdered him, and his death is the reason Link quit the card-hustling game. Cookie is Link’s ex-wife who cheated on him with a number of other men, including Booth. Oddly, neither brother speaks ill of her. Grace is Booth’s paramour, though the two seem to be constantly engaged in an on-again, off-again relationship. Booth shoplifts an engagement ring for her and prepares a formal dinner at his apartment, but Grace rebuffs all his advances. At the end of the play Booth becomes increasingly agitated by her disinterest and, off stage, goes to her house and shoots her.