Anne Roiphe saw the best minds of her generation—or at least several good ones—destroyed by madness; hysterical and often naked, these men were thirsting, for artistic glory and another Scotch. This is the tale told in Art and Madness (Nan A. Talese; $24.95), in which Roiphe re-creates her “lost years,” those “never touched” by her previous three memoirs. Roiphe’s reputation as a writer precedes her, and that is a good deal of her new book’s appeal. Was this second-wave feminist really once a shy Jewish girl who worked at a public relations firm and happily typed the manuscripts of her playwright husband? Complementing the question is the time and place, the New York publishing world of the 1950s and ’60s, when “editors and writers went out to three-martini lunches” and “absurdity was very fashionable.” On the inner-workings of the literary myth machine, Roiphe delivers, explaining how a scuffle between Norman Mailer and Doc Humes became legend in the span of a smoked cigarette: “constellations in the sky were named after the encounter.”

Male writers found in alcohol “the lubricant of genius” and found in women like Roiphe willing muses and amanuenses—who also picked up the kids from school and bills at bars. She insists, though, that it takes two to make an accident. The real madness for Roiphe was her own, and in her efforts to dissect her former self’s ecstatic devotion to a man’s work, she can fail to sympathize with young Anne. Part of the problem is stylistic: her combination of narrative detachment and spartan prose creates distance, not intimacy. The choice is interesting but self-defeating. Four-fifths of the way through the book, she writes that her first husband “could not stay any longer. He moved out within the week.” In the next paragraph she speaks of her younger self in the third person: “I have no pity for her…. I have no pity for that about-to-be-divorced woman who had been ready to live off the written words of someone else.” Moments of the memoir are deeply affecting—her sexual conquest of George Plimpton, King of the Gentiles, is as riveting as Victor Laszlo’s singing of “La Marseillaise” in Casablanca—but spending so much time with a writer who possesses little empathy for her protagonist is tiresome.

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Authors of late-in-life memoirs about their youth have at least two fixed characters that must emerge in full from the past—the subject and the setting—although the balance between them is negotiable. Our interest in both is rooted in sympathy, to feel that two things are the same and different simultaneously, and a good writer makes that possible, even inevitable. The project of Millicent Monks’s Songs of Three Islands (Atlas & Co.; $24) is no less compelling than Roiphe’s, if not more so: tracing mental illness—borderline personality disorder and schizophrenia—as it runs down the trunk of the Carnegie matrilineal family tree. Her mother, Lucy, at 18 wed a handsome blue-eyed man, and one summer night, not long after the marriage, she playfully dressed as a nun and rowed out to see what her husband was doing on a yacht—drunkenly philandering, it turned out, and “Lucy was never quite as beautiful as before.” It’s a scene not easily forgotten. So, too, when Monks was 9 and at night her catatonic mother took to hiding behind velvet curtains and drifting like a ghost to the attic. Monks rarely fell asleep before 4 am, occasionally talking to her stuffed animal: “‘It’s alright, Dazzle, I’m not crazy. I am going to be good.’”

In this memoir of reckoning, Monks flits where others might dwell (carving-knife suicide, foiled kidnapping plot), showing it’s not events that make a life interesting to read about but how the writer traces their impression. But when it’s time for a similar 4 am scene now involving her own daughter, Monks gives us less: how did she feel to be awakened by the telephone, a wild child on the line slurring the old accusation that she had never been loved? We don’t know what she said to her husband, who, unlike Dazzle, could have responded.

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Pitch Uncertain, by Maisie Houghton, (TidePool Press; $24.95) is a linear account of home life and schooling. It is Houghton’s first book; there is no sensational drama. Her comfort with, even delight in, the ordinary, as well as a humble authorial ambition, are what make the book a success. She renders a detailed topographic map of the 1950s East Coast WASP kingdom—from Massachusetts to Maine—with its emotional landscape defined by landmarks like the hump that gradually rose in the middle of her parents’ bed and Gran’s evergreen motto, “Least said, soonest mended.” Like the mattress’s ridge line, Houghton is in the middle, growing up flanked by two outspoken sisters. The small moments stick like New England burdock: she was mesmerized by a music box as its “fat cylinders stuck with rows of spiny prickles slowly churned.” What are those metal bumps called, if not “spiny prickles”?

Houghton explains in her final chapter that after decades of not writing, having hewed to her safe middle path (supportive wife, dedicated volunteer), she completed but never published a book about her rebellious actress cousin. That, too, proved to be “another good-girl approach—the Radcliffe way: attack, research, tie up the loose ends.” And so, at 70, she decided to write about the one person she’d learned not to let speak. Her long silence on the subject allowed her to hit the right pitch, reminding us that the act of writing is realizing: if a writer doesn’t discover much while working, the reader will discover far less.