Simon is famous for writing light domestic comedies that became major box-office hits. Of twenty-six plays produced in the thirty years before Lost in Yonkers, all but five attracted large audiences and earned Simon a multimillion-dollar fortune. Critics, less enthusiastic than his faithful fans, questioned his lack of interest in formal experimentation and often dismissed him as too prolific, mechanically creating gag-laden comedies. Although touring companies performed his plays to packed houses across the United States, and his plays were successfully produced in Great Britain and many foreign countries, Simon complained that his reputation as a lightweight kept many regional theaters from performing his work.

Critical attitudes began to change with the appearance of the Brighton Beach trilogy. The themes of the plays seemed more significant than critics expected, especially the presentation of a parent-child conflict in Broadway Bound. Some critics were even willing to concede that many earlier plays, previously written off as lighthearted comedies, actually portrayed the deeper dynamics and difficulties of personal relationships.

Lost in Yonkers received even more praise than the trilogy, winning Simon a Tony Award for best play and a Drama Desk Award. Although Simon predicted that he would never win a Pulitzer Prize, Lost in Yonkers won the 1991 award for drama. Many critics termed it Simon’s best play—his least sentimental and most satisfying dark comedy, mining its humor out of very painful material. Not all reviews were completely positive, but most agreed that Simon had written an honest and compelling examination of family conflict, singling out the scenes between Bella and her mother for special praise. Some critics questioned the slow exposition of the family situation at the start of the play; others liked the plot up until its happy ending, calling it a forced and unconvincing conclusion for such a wrenching drama. Only Mimi Kramer in The New Yorker was wholly negative, finding nothing honest or authentic in the entire play. Despite Simon’s fears, regional and collegiate theater groups have added Lost in Yonkers to their repertoire.