The year is 1942; the scene is the living and dining rooms of Grandma Kurnitz’s apartment above Kurnitz’s Kandy Store in Yonkers, New York. Two young boys, Jay and Arty, wait in the living room while their father, Eddie, asks Grandma in her bedroom to take the boys for a year; he needs to travel to earn money and repay loan sharks from whom he borrowed to pay for his dead wife’s cancer treatment.

The boys fear their grandmother, who walks with a limp, her foot having been crippled during an anti-Semitic demonstration in her native Germany. She is convinced that only hardness can succeed in the world, and her sternness in raising her four surviving children has psychologically damaged them. Eddie trembles in fear when he speaks to her. Another son, Louie, has become a small-time gangster and is hiding from his associates in his mother’s apartment. Daughter Bella is mentally retarded. Gert gasps for breath when she talks to her mother.

The passage of time is indicated by blackouts during which Eddie reads letters to his sons describing his travels across the South dealing in scrap iron needed for the war effort. Act 1, after establishing the psychological problems of the characters, ends with a voice-over in which Eddie tells the boys how pleased he is that they are safe in the care of his family.

Simon mines humor from the play’s grimness. Critic David Richards remarked that, “Were it not for his ready wit and his appreciation of life’s incongruities, Lost in Yonkers could pass for a nightmare.” Uncle Louie praises his mother’s stoicism, noting that, although her injured foot aches constantly, she will not even take aspirin to ease the pain. Simon gets a surefire laugh when Arty later tells his brother, “I’m afraid of her, Jay. A horse fell on her when she was a kid and she hasn’t taken an aspirin yet.”

The dramatic center of the play is Bella’s struggle to find emotional support and fashion a life of her own, despite opposition from her mother and the incomprehension of her siblings. Bella appears a comic figure as she tells her relatives around the dinner table that she has met a similarly retarded usher at a movie theater and that the two plan to marry and open a restaurant. Louie mockingly asks whether what the usher really wants is her money, but Simon abruptly stops the audience’s laughter when Bella cries “He wants me! He wants to marry me!” Grandma does not deign to respond, but silently rises and goes to her bedroom.

Louie advances Bella money to open a restaurant, but her boyfriend proves too timid to leave the safety of his parents’ home, and her plan fails. At play’s end, when Eddie returns from his travels to reclaim the boys, Bella is still living with her mother, but she establishes some independence by inviting newfound friends to dinner.

Lost in Yonkers won a Tony Award for best play. Although Simon believed that his reputation as a comedy writer precluded his ever being given a Pulitzer Prize, the play also won the 1991 award for drama. Many critics consider this powerful dark comedy to be Simon’s masterpiece.