Simon's mature theater work combines comedy with moments of poignance and insight. Examples abound. In The Odd Couple, Oscar Madison and Felix Ungar, although hilarious to see and listen to, demonstrate how destructive a selfish person can be. Promises, Promises dramatizes how Chuck Baxter and Fran Kubelik, who think they can manipulate people at no cost to themselves, learn that others, more shrewd and calculating, manipulate them and make them pay heavily for their proud schemes. The exchanges between Bill and Hannah Warren in California Suite reveal how easy it is to misjudge who is the strong person and who is the weak, and to fail to perceive that although two people talk at length about one topic, their views on that topic merely reflect thoughts and feelings rooted in more fundamental aspects of their lives. Plaza Suite, The Sunshine Boys, and Chapter Two also do a superb job of fusing the comic and the insightful.

Another recurring feature in Simon's plays is the humor itself. It might seem facetious to state that Simon's plays are consistently—at times, dazzlingly—funny. But much too often this primary component of his work is taken for granted. It is not true that all of Simon's hit shows consist of clusters of funny one-liners. Yet even if it were true, it would be no small accomplishment. Precious few people can write any kind of funny lines…. In the 1961–1981 period, Simon's success in creating page after page of laugh-provoking dialogue is unmatched by any other playwright's efforts. Indeed, very few playwrights have matched his achievement during any twenty-year period.

Simon admitted that early in his playwriting career he was guilty on occasion of stuffing a one-liner into some character's mouth. Quickly, though, he weeded out such lines from the drafts of his newer plays; and, soon, all the humorous conversation emanated from the plot and characters. If, then, while discussing Simon's work chronologically, one gradually stops quoting funny lines, it is not because they dwindle in number. There are as many funny lines in the conversations between Diana and Sidney Nichols as there are in those between Corie and Paul Bratter in Barefoot in the Park. In the best later plays, however, the richness of character delineations and related matters demands that a discussion of these works concentrate on quotations pertaining to character and theme.

Simon does, on the other hand, sometimes have problems with his plays' structure. Fools, which gives little attention to characterizations and, instead, focuses on its fairy-tale story, is woefully weak in structure. The plot barely moves forward in the first part of the play; in the remainder, it has far too many twists and turns. Come Blow Your Horn is repetitious in construction and too contrived at times. Barefoot in the Park dramatizes a tension between Corie and her mother, then suddenly drops the whole matter. Happy endings that are not entirely convincing occur in several plays, including The Odd Couple, I Ought to Be in Pictures, and, most clearly of all, The Gingerbread Lady. A few plays, however, are exceptionally sound in structure. For example, Chapter Two deftly intertwines its complicated major and minor plots. In California Suite, the lurking fundamental problem in the relationship between Diana and Sidney Nichols is adroitly set up step by step until it finally declares itself—a declaration causing a major crisis in the Nicholses' marriage. The Sunshine Boys has an airtight structure.

With regard to character delineation, Simon has no peers among contemporary comedy playwrights. Other writers have created vivid characters—but not in the sheer abundance Simon has. Even if one leaves aside the captivating broad comedy characters found in such plays as The Good Doctor, Plaza Suite, and California Suite, plus the liveliest characters in all the musicals, there are still numerous compelling characters, major and minor, in the more realistic comedies. To cite only one play's excellently sketched minor characters, there are the feckless musician Lou Tanner and the homosexual actor Jimmy Perry in The Gingerbread Lady…. (pp. 139-41)

Another dominant feature of Simon's work is his outlook on life. As is true for all other outstanding writers of comedy, Simon humorously dramatizes his serious basic beliefs. Through his characters, he suggests that the individual should choose to remain within the social network. No Simon hero or heroine makes the ultimate Romantic gesture of thumbing his or her nose at society…. Simon's emphasis in [his] early plays on the desirability of working within society remains undiminished in his later works. In Last of the Red-Hot Lovers, for instance, Barney Cashman's attempts to break free of society's conventions render him comic, not heroic. In all his plays from Come Blow Your Horn to his most recent work, Simon honors the ultimate symbol of the social network: the family unit. (pp. 141-42)

This stress not on the primacy of the individual, but on the primary importance of society has triggered negative reactions in several critics. Some critics, assuming that Simon's "old fashioned" beliefs constitute no beliefs at all, declare his work flimsy and superficial. Most members of the audience, however, are delighted to find Simon upholding their own beliefs. Simon's point of view, though, does not arise simply out of a desire to pander to the beliefs of the "moral majority." Simon opts for society because he sincerely believes that human beings are frail creatures who will be less vulnerable to attack and more likely to thrive if they seek the nourishment society provides.

By no coincidence, then, two virtues Simon stresses are moderation and fidelity. To function well within society, one must compromise. To compromise, one must be mature enough willingly to embody moderation. Too much ego or self-love, found in Oscar Madison and Felix Ungar, for example, is destructive…. Rarely, if ever, do those who pursue sexual infidelity gain happiness….

[And, in] Simon's eyes, divorce is never a victory. (p. 142)

Although the moral beliefs that Simon advocates are "old-fashioned" ones, his view of human experience is not blithely sentimental. The happy endings in his best plays are often only minimally happy. Chuck Baxter and Fran Kubelik finally get their lives on the right track, but they have been deeply scarred in the effort and are more than a little gun-shy emotionally. Equally scarred are the Nicholses and George Schneider and his wife, Jennie….

Simon also acknowledges the complexity of human experience. Last of the Red-Hot Lovers shows that guilt feelings can lead to moral conduct that, in turn, brings happiness and a sense of relief. But both Chapter Two and Fools demonstrate that guilt feelings can be negative, destructive forces. Simon celebrates love and tenderness in Promises, Promises, yet in that same play points out that people must be tough in order to defend the love they feel and share. The meetings between Muriel Tate and Jesse Kiplinger in Plaza Suite and between the Warrens in California Suite portray how a simple course of action can be ladened with a bewildering complexity of conflicting motivations. Furthermore, Simon reveals in play after play how greatly the fear of aging and dying complicates every human being's life.

Simon emphasizes the need for honesty, yet he demonstrates that honesty does not always provide a solution to troubles. Honesty can be more destructive than creative. Karen and Sam Nash's discussion "clears the air" between them, but their frankness renders a formerly difficult marital situation impossible. (p. 143)

Finally, however, Simon does suggest that, if risked, honesty can ultimately prove constructive. Corie and Paul, Diana and Sidney, Jennie and George—many of Simon's couples—engage in bluntly honest exchanges and, as a result, pave the way toward better, stronger relationships. Both Barney Cashman and Faye Medwick feel relieved and legitimately optimistic after they admit to themselves that they are simply not cut out to be "swingers." Willie Clark gains at least a modicum of peace when he accepts the fact he is now an old man.

Walter Kerr has stated, "Whenever a playwright manages to be hilariously funny all night long … he is in immediate danger of being condescended to," Because Americans have always tended to underrate writers who make them laugh, Neil Simon's accomplishments have not gained as much serious critical praise as they deserve. His best comedies contain not only a host of funny lines, but numerous memorable characters and an incisively dramatized set of beliefs that are not without merit. Simon is, in fact, one of the finest writers of comedy in American literary history. (p. 144)