Eugene O'Neill's Pulitzer Prize-winning play, Long Day's Journey into Night (1956), is an autobiographical piece that explores a single day in the tumultuous life of the Tyrone family. The youngest son, Edmond, is battling tuberculosis and harbors deep resentment toward his father. Meanwhile, the mother struggles with drug addiction, and the older son grapples with alcoholism.

Simon's Brighton Beach Memoirs (1982) is the first installment of his autobiographical trilogy, which also includes Biloxi Blues (1984) and Broadway Bound (1986). This play portrays the Jerome family, a Jewish household dealing with financial difficulties and interpersonal conflicts while residing together during the Great Depression.

In his second memoir, The Play Goes On (1999), Simon reflects on his later years and professional journey, starting with the period after the death of his cherished wife, Joan.

Simon's initial memoir, Rewrites: A Memoir (1996), received critical acclaim for its exploration of the early stages of his life and career, culminating in the passing of his wife.