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 Roiphe The 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.