Midway through Brighton Beach Memoirs, the first play of Neil Simon’s autobiographical trilogy, the playwright has his fictional stand-in make a confession directly to the audience. “How am I going to become a writer,” asks Eugene Morris Jerome, just shy of 15 and already full of artistic yearning, “if I don’t know how to suffer?”In the very next sentence of the monologue, Simon dispels that grave and nagging question with a punchline. Feeling the fever of puberty, knowing there is dessert waiting downstairs in the kitchen, Eugene cracks, “Actually, I’d give up writing if I could see a naked girl while I was eating ice cream.”The bracing challenge and expedient retreat contained in that one short moment reveals a great deal about Neil Simon’s own gifts, anxieties, defensiveness, and ambition. The question Eugene raises is not rhetorical. It is the same one critics often asked of Simon as he became a Broadway staple and commercial phenomenon with comedies like The Odd Couple, Chapter Two, and The Sunshine Boys. And just as Eugene humorously deflates the issue of creativity and misery, so did Simon for the first 30 years of his career pull back from darker material to the default setting of getting lots of laughs.As a matter of historical fact, though, Simon never needed to wonder if he had suffered sufficiently. His own youth in a turbulent home during the Great Depression supplied more than enough. The question was when, if ever, he was going to plumb the personal depths. The trilogy of memory plays first produced over a six-year period in the 1980s—Brighton Beach Memoirs, Biloxi Blues, and Broadway Bound—provided the answer, an answer that evolved with the progression of the plays themselves.Now, Simon’s longtime producer Emanuel Azenberg is reviving the first and last of those plays in repertory. (Brighton Beach Memoirs opened on Oct. 25, and Broadway Bound starts previews on Nov. 18 and has its opening night on Dec. 10.) These productions, under the guidance of the acclaimed young director David Cromer and with Laurie Metcalf heading the ensemble cast, show how Simon struggled with and ultimately faced up to his memory’s demons. Taken together, Simon’s portrayals of the Jerome family deserve to stand with the work of Clifford Odets and Arthur Miller as definitive theatrical treatments of the American Jewish family in extremis.Born in 1927, Simon is a full generation younger than Odets and a dozen years younger than Miller, and the distinction matters as more than trivia. The two older playwrights went through most or all of the Depression as adults, and came of age during the Popular Front era with its fervent left-wing politics. Simon experienced the Depression as a child, and its depredations coincided with the upheavals in his parents’ marriage.So while Odets and Miller reckoned with the Depression very much in political terms, as a failure of the false god of capitalism, in Simon’s household financial calamity was conflated with familial collapse and marital betrayal. But it took him a long, very long time, to tell that story.Instead, he honed his craft alongside Mel Brooks, Woody Allen, Carl Reiner, and Larry Gelbart on the writing staff of Sid Caesar’s Your Show of Shows. Turning to theater, Simon expertly worked the theme of conflict—with the newlyweds of Barefoot in the Park, the divorced men rooming together in The Odd Couple, the feuding vaudevillians of The Sunshine Boys—without ever plunging deeper and risking an unhappy ending. When he turned serious, in the wake of his first wife Joan’s death at age 40 from cancer, he did so in a schematic, grad-student kind of way, doing his version of Chekhov in The Good Doctor and the Book of Job in God’s Favorite.The darling of a mass audience, Simon was the favorite whipping boy for cultural mandarins. His expertly crafted comedies received condescending sniffs, partly because of their expert craft, and his attempts at drama were smacked down with a ferocity meant to make him know his place. At one time in the 1980s, when August Wilson was serving on an awards committee of the Dramatists Guild with two other playwrights, he nominated Simon for a career-achievement award. The other two scoffed in such derision that Wilson later wondered what possibly could have caused such animus.During the mid-1970s, though, Simon had written 35 pages of a memory play called Brighton Beach Memoirs. Aware that it was “a turn in style for me, probing more deeply into myself,” as he later put it in a Paris Review interview, Simon stuck the partial manuscript in a drawer for nine years.If Simon could only tiptoe at that point into his family history, rather than fully immerse, then one can understand the reluctance. Simon’s mother, Mamie Levy, had been disfigured as a young girl, scarred inside and out when her dress caught fire. The man she married, a piece-goods salesman named Irving Simon, left the household “as least eight different times” for periods ranging from a month to a year, Simon recounted in his memoir, Rewrites. In his absence, Mamie gave up her bedroom in the family’s Washington Heights apartment to two tenants, butchers who paid half their rent in cash and the rest in unsold meat. She also ran card parties, essentially a small-scale gambling parlor, to make money.On the occasions Irving Simon did return home, he specialized in a certain kind of emotional torment, not just to his wife but to Neil. He would buy fireworks for the boy’s birthday, then hand them all out to other kids, claiming he didn’t want Neil to hurt himself. His means of expressing tenderness was to tell Neil to pull a stick of gum or piece of candy from the stash in his overcoat pocket. One time, Mamie brought Neil to stand outside the apartment building of Irving’s mistress, so that the child could witness and even testify in court to his father’s infidelity. When Neil ran a high fever that his mother’s cold compresses couldn’t break, he recalled in Rewrites, “She would curse my father for his absence and run out to the hallway, banging on the doors of neighbors to help her find a remedy, screaming up to a God who had once again abandoned her.”Even these public recollections did not come from Simon until the 1990s. The first inkling all but his closest friends had of his actual upbringing came with the autobiographical trilogy. And in the original production, the emotional honesty came fitfully. In a vivid and indelible way, Brighton Beach Memoirs does convey the fragility of subsistence during the Depression. Any bump or twist to the family breadwinners, whether an injury or a shop shut-down or a 17-dollar loss at poker, brings penury right to the threshold.In the current revival, director David Cromer has raised the grain on the serious aspects of the play, and thus diminished the quaint ones, much as he did in his highly praised production of Our Town. And in this production, it is the beleaguered but resourceful mother Kate Jerome, indelibly embodied by Laurie Metcalf, rather than exuberantly youthful Eugene who commands the psychic center of the action.Yet, as Simon himself later acknowledged, the Jerome family in Brighton Beach Memoirs was “the family I wished I’d had instead of the family I did have.” The father Jack, a garment worker, valiantly takes on second and third jobs to keep the household afloat. The mother Kate argues bitterly with her sister Blanche but reconciles. Jack’s cousin in Poland miraculously escapes with his wife and children and, at the play’s final curtain, the refugees are heading toward their waiting relatives in Brighton Beach. And the character of Eugene, especially as played by the young Matthew Broderick, put an infectiously charming patina on all the goings-on.In ways that may have been precise engineering or may have been intuitive candor, Simon also wrote some passages in Brighton Beach Memoirs that would lay explosive charges for Broadway Bound. At one point in the play, for instance, Kate says to Jack about the bookkeeper in the garment factory, “Just promise me one thing. If anything ever happened with you and that Helene, let me go to my grave without hearing it.”As the final chapter of the trilogy reveals, she does not get such blissful ignorance. If Brighton Beach Memoirs was Simon’s equivalent to Eugene O’Neill’s sunlit fantasy of family life, Ah, Wilderness, then Broadway Bound was the closest thing in his oeuvre to A Long Day’s Journey into Night. For all of its lighter elements, most involving Eugene and his older brother Stanley starting to make it as comedy writers, Broadway Bound is surely, as O’Neill described his own masterpiece, “a play of old sorrow, written in tears and blood.”Where Brighton Beach Memoirs opens with Eugene joyfully practicing his baseball pitches, Broadway Bound raises its curtain on Kate’s elderly father sneaking out of the Jerome house with the bedsheets he had soiled. That Kate discovers him in the act is the first indication that, in this play, the dirty linen will indeed be aired. The indomitable Kate of the first play, who assures her worried husband that “God has time for everybody,” is by now bitter and suspicious; the audience is told, as it wasn’t in the first play, that similarly to the actual Mamie Simon she “burned half the skin off her back” in a garment-factory fire.As for Jack, the steadfast provider in Brighton Beach Memoirs has aged into an ineffably unhappy and serially unfaithful man. “If I’m not enough for you anymore, then tell me and get out,” Kate declares. A bit later, in as naked a sentence as he ever wrote, Simon has her ask, “How is it possible I could hate you so much after loving you all my life?”Simon grants Kate a touch of redemptive escape when Eugene coaxes her into remembering and reenacting the high point of her womanly life—the time in a ballroom decades earlier when the movie star George Raft asked her to dance. This is no happy ending, though; this is the tragedy of unfulfilled life and shattered dreams; this is Mary Tyrone in her morphine haze recalling the doting sisters at her convent school, the one she left when she met the dashing actor James Tyrone.The Eugene of Broadway Bound, 23 years old, intones some of the lessons about writing this his creator certainly learned, too. Writing a joke isn’t the same as writing comedy. And writing about the people you know sometimes means hurting them in the process. Eugene worries aloud that he is divided between “this nice likable funny kid” and “the part that writes, that’s an angry hostile real son of a bitch.”Neil Simon kept that part of himself caged for a long time. When he liberated it in the trilogy, he set free part of his talent, too, the part that won the Pulitzer Prize for Lost in Yonkers. He didn’t lose the ability to entertain his audiences, but he did take a hint from something the grandfather says in Broadway Bound: “I don’t trust affection. Sometimes people give it to you instead of truth.”Samuel G. Freedman is a journalism professor at Columbia University and a regular contributor to Tablet. He also writes the “On Religion” column for The New York Times.