A writer’s dying can seem the coda to his work, since one definition of the poet and novelist is, or should be, someone who’s been preparing to die all along—someone whose imaginative life is usurped by the inevitability of our flesh, and the consequences that inevitability has for the spirit. Death, says poet-critic William Empson, is “the trigger of the literary man’s biggest gun.” The writing of literature and the reading of literature don’t have many junctions, but preparation for death is one of them. Whatever else it may become, writing remains a stay against our fate in that the writer attempts to parse that fate and then lets the rest of us know what he’s found.

The critic who parses the artist parsing death must be every inch as intrepid as the artist himself. In The Violet Hour, Katie Roiphe delivers a composite of daring beauty on the deaths of Susan Sontag, Sigmund Freud, John Updike, Dylan Thomas, and Maurice Sendak, a necessary report from “the deepening shades,” as Yeats has it, rife with her hospitable authority and critical rectitude. For the duration of this book, the dark night of Roiphe’s subject becomes lit by her limpid grasp of the psyche de profundis, by the grit and thew of her scrutiny. The author of four previous books of nonfiction and one novel, Roiphe writes of “the violet hour” with an unassailable dignity and a consummate lack of bathos. (The phrase is T.S. Eliot’s, from The Waste Land: “the violet hour, the evening hour that strives / Homeward.”) Here is a critic in supreme control of her gifts, whose gift to us is the observant vigor that refuses to flinch before the Reaper.

Each chapter, skillfully eliding overlap, constitutes a “biography backward, a whole life unfurling from a death.” In the slow fade of her five writers—cancer came for Sontag, Freud, and Updike; a stroke felled Sendak; Thomas decimated himself exuberantly with drink—Roiphe finds “glimpses of bravery, of beauty … of truly terrible behavior, of creative bursts, of superb devotion, of glitteringly accurate self-knowledge, and of magnificent delusion.” Death approaches unbidden and demands you “put away,” says Emily Dickinson, your “labor” and your “leisure.” Her use of “labor” summons Christina Rossetti’s line “Of labor you shall find the sum”: All of our earthly strivings have the same outcome—death is the great leveler. “I think if I can capture death on the page,” writes Roiphe, “I’ll repair or heal something. I’ll feel better. It comes down to that.” Yes it does; it comes down to virtually nothing else. “I want to see death,” she writes, and “to see the world I’ve always opened a book.” That’s a fine encapsulation of why literature matters: It permits you to see past yourself, to see the world, and death is an integral element of that world. Next to being born, dying is the most important thing that ever happens to you.

A distinction must be made between those who sought their deaths and those who fought them. Freud was uncommonly devoted to tobacco; even after he became certain it would kill him, he smoked with an erotic intensity. (Roiphe’s meditation on his smoking is one of the book’s many gems.) Dr. Johnson might have said a sick man can’t help but be a scoundrel, but Dr. Freud proved otherwise. He seems to have been not just genuinely resigned to dying but genuinely unafraid of it, too. Rousseau has a passage in his 1761 novel Julie about how there’s no such thing as fearlessness in the face of death, that we must be very afraid or else the species would self-destruct. In that, Freud proved as obstinate as in all else. Roiphe sees him as having a “rational acceptance of the stony path that leads us out of existence … because the alternative is unthinkable: to fear death, to deny it, to rage against it, to be, in other words, out of control.” In his eighty-third year, he died as he wished, at home in London, his last reading pleasure a Balzac novel, his disciple and daughter Anna at his bedside. The lifelong master of control—of his work, of his legacy, of the art form he founded—was not about to give it up at the close.

THE VIOLET HOUR: GREAT WRITERS AT THE END by Katie RoipheThe Dial Press, 320 pp., $28

That dervish Dylan Thomas, on the other hand, was an epic relinquisher of control, a drinker of otherworldly virtuosity. In the fifteenth-century morality play that bears his name, Everyman says to Death, “Thou comest when I had thee least in mind,” but Thomas was almost never free of his deathward lean. Like Rilke before him, he fancied himself death’s plaything in one mood, death’s playboy in another. Roiphe quotes aptly from Thomas’s letters and poems, though she misses this bit from a letter he penned as a self-wallowing 18-year-old: “Death stinks through a thousand books.” And this one from the year before: “The majority of literature is the outcome of ill men.” To that line he appended this: “I am always ill.” So you see the romance Thomas was having with himself, a romance that started young and never stopped.

Thomas enjoyed “the theater of sickness,” Roiphe writes, because he “found illness a convenient language for his skewed relation to normal life, for his inability at times to function.” The illness factor in alcoholism appealed to him, at a time when people called it a weakness instead of a disease. Biographers differ on how many straight whiskeys Thomas downed before he dropped into a coma in New York City at the age of 39, but 18 is the number that keeps coming up. A Byronic self-mythologizer, Thomas knew that talent, sex, booze, and early death are the golden quartet of literary immortality. Though that’s an outsized ambition with a high rate of failure, it happened to have worked for him. Good advice, that famous line about raging “against the dying of the light,” but few poets ever raged so feelingly into darkness.

Where Freud and Thomas might have been imprudent, Sontag and Updike were exceedingly sane, nondestructive, engined by an incorruptible will to live. Roiphe quotes Sontag’s line, “One can’t look steadily at death any more than one can stare at the sun” without noting that it is an annexation of La Rochefoucauld’s maxim, “Death and the sun are not to be looked at steadily.” But Sontag was forced to look. To the attempted blitzing of her cancer, she brought the selfsame ferocity of will she’d brought to her life and work. She sought whatever medical scorchings and strafings might stand some chance of helping her, of adding days to her truncated calendar. As an intellect and personality she was afraid of nothing, of nobody, and so she appeared to believe that cancer was one more foe she could vanquish by sheer superiority of assertion; she had, after all, beaten it twice before. “Brave” is the cliché tirelessly attached to one’s struggle against cancer, but for Sontag, the cliché wouldn’t do—she was caustically heroic when she wasn’t pointlessly petulant.

Sontag wore her snobbery like a red velvet robe, and that’s one way to do it, I suppose. She seemed often to forget the basic moral arithmetic which says that while fierceness on the page is necessary, fierceness in person is not. It’s hard to take her insolence to friends and nurses who say the wrong thing in their attempt to say the right thing. Death makes us bumble, renders language more inadequate than it normally is, and those who fail to recognize that are missing a fundamental fact of being human. At the age of 16, an incurably precocious Sontag wrote in her notebook: “How is it possible for me to stop living … How could anything be without me?” Her self-regard was so unconquerable that she considered her dying a cosmic discourtesy.

Roiphe flashes her richness of mind most intently on Updike. In Updike’s work, “one is struck not by the glittering seductions of the sharp, ambitious, sexually enthralling mistresses but by the deep, agonized love the husbands feel for the first wives.” She commands a supercharged insight into Updike’s religio-sexual realm that many critics, female and male both, are too ideological or outright panderly to muster. She knows that true criticism does not bother with the mollification of delicate sensibilities, only with the intellect as it roils and rollicks through language.

Whole swaths of Updike’s work are “about not submitting gratefully to that eternal sleep, cheating, tricking, denouncing it, protesting it, fixating on it; so much involves the hope for more than our animal walk, an afterlife or, better yet, more life.” His unkillable buoyancy of language, his style that pursued every contour and lineation of living: No other major American novelist has been so downright delighted by the tensile strength of English, no one else so wedded to the notion of writing as deliverance. Empson says of death: “I feel very blank upon this topic / And think that though important, and proper for anyone to bring up / It is one that most people should be prepared to be blank upon,” but for Updike blankness was never a possibility. Of his last poems, Roiphe writes:

He scrawls through rage, bitterness, bile, jealousy of the living; he works through nostalgia, fond slippage into the past, bewilderment. He writes through magical salvation, resurrection. He imagines himself reading his own death: “Endpoint, I thought, would end a chapter in / a book beyond imagining, that got reset / in crisp exotic type a future I / —a miracle!—could read.” He is writing his way out of death; he is dreaming his way past or through it.

A book about writers dying, The Violet Hour is also about those who congregate around them as they do: Tony Kushner’s loyalty to Sendak, Annie Leibovitz’s to Sontag, Anna Freud’s to her father. The dying of a loved one can also underline all of our most grating qualities. Caitlin, Thomas’s wife, says of his hospitalization: “It was like a super melodramatic spy story … with all the characters suspecting each other of the vilest motives.” That makes a near-accurate description of Sontag’s dying, too, her friends and family sometimes jostling for dominance of the indomitable. We see here the appalling callousness of Updike’s second wife, Martha, toward Updike’s first wife, Mary, and toward Updike’s own children, a callousness for which she seems to have had Updike’s unspoken approval, and not only during his final days. That doesn’t sit well: We want our literary heroes to be decent people off the page, despite our knowing that personal decency has nothing to with their effectiveness on the page.

In his poem “The Last Invocation,” from Leaves of GrassWalt Whitman writes, “Let me glide noiselessly forth,” and that sounds ideal, but a demise can contain multitudes, a bartering between riot and calm. We’ve seen recently, in last testaments, the multiform ways to cope: the sentimentality of Oliver Sacks in Gratitude, the trademark recalcitrance of Christopher Hitchens in Mortality. In Latest Readings, cancer-stricken Clive James has this to say: “If you don’t know the exact moment when the lights will go out, you might as well read until they do,” because “the childish urge to understand everything doesn’t necessarily fade when the time approaches for you to do the most adult thing of all: vanish.” If literature indeed helps you understand, why read when there’s but scant living left, when your understanding won’t do you any good? Because the dying aren’t always dead to pleasure, and for a writer at the end, the knowledge of literature still gives the most pleasure of all. “We won’t be taking our knowledge any further,” says James, “but it brought us this far.”