The Odd Couple is one of many plays in which Neil Simon explores human relationships on the family level as well as the wider social level by pairing opposites and placing them in situations that force them to deal with each other intimately. Other notable examples of the technique include Come Blow Your Horn (pr. 1960), which shows two brothers in conflict with each other and with parental authority. Barefoot in the Park (pr. 1963) pairs Corie and Paul Bratter, a young honeymooning couple of conflicting personalities attempting to begin a life together in their first apartment. In The Star-Spangled Girl (pr. 1966), Simon mixes two politically radical young writers, Andy Hobart and Norman Cornell, with the ultraconservative Olympic swimmer Sophie Rauschmeyer. All three must deal with conflicting emotional and physical attractions, as well as conflicting political and social commitments. Chapter Two (pr. 1977) unites George and Jennie in a second marriage. Jennie wants to get on with her life after her disastrous first marriage, but George is reluctant, filled with guilt over having found happiness so soon after his first wife’s death. I Ought to Be in Pictures (pr. 1980) revolves around the conflicts of an insecure writer and his aggressive young daughter, who has come unexpectedly to live with him in Hollywood. In this play, as in the others, both family and romantic relationships are explored through Simon’s comic vision of a life filled with incongruities.

Simon has been criticized by some for turning out the same kind of play again and again, but, aside from their all being comedies, his plays exhibit a wide variety in style, quality, and characterizations. Throughout his career, Simon has experimented with a variety of styles. Plaza Suite (pr. 1968) and California Suite (pr. 1976) utilize the format of a series of single acts. Last of the Red Hot Lovers (pr. 1969) is similar in structure, except that it is built around one character, Barney Cashman, and his attempts to seduce three different women in three separate acts. Simon’s plays vary from situation comedies such as The Odd Couple to satirical musicals such as Promises, Promises (pr. 1968). His techniques range from vaudeville skits (as in The Sunshine Boys, pr. 1972) to the use of fables (Fools, pr. 1981). Simon has also borrowed from the mystery/detective genre for his screenplays of Murder by Death (1976), The Cheap Detective (1978), and Seems Like Old Times (1980). He has borrowed from other sources to write The Heartbreak Kid (1972), a screenplay based on a short story by Bruce Jay Feldman, The Good Doctor (pr. 1973), based on stories of Anton Chekhov, and God’s Favorite (pr. 1974), based on the Book of Job.

In most of his plays, Simon creates characters who are typical middle-class Americans in an urban setting, beset by conflicts and problems common to all people. His earlier plays, particularly The Odd Couple, Barefoot in the Park, and Plaza Suite, deliver his message of relationships and compromise through a succession of highly amusing one-liners, yet the characters exhibit marvelous human complexity. Simon shows the good and bad sides of his characters as they suffer through guilt, conflicting motives, and love and tenderness. His later works Brighton Beach Memoirs (pr. 1982), Biloxi Blues (pr. 1984), and Broadway Bound (pr. 1986) are more autobiographical and more concentrated on theme and character.

In all of his plays Simon humorously, often hilariously, dramatizes his outlook on life and his basic beliefs: the value of working within the prevailing system, the need for compromise, the ultimate value of honesty, the sanctity of the family unit, and the destructiveness of selfish behavior. He is not afraid to mix the painful and the ridiculous with his social comment. These traits have made Neil Simon one of the most successful playwrights of the twentieth century.