For a book about writers at the time of their deaths, Katie Roiphe’s The Violet Hour: Great Writers at the End, is most intense at its birth. The prologue recounts the book’s genesis in the author’s childhood illness. At the age of 12, she begins to suffer recurring bouts of pneumonia, and during a stay in the hospital, the heart of her roommate, a baby, stops during treatment.

“This is when I start writing this book,” Roiphe explains, in a literary present that shapes many of the book’s meditations, not only on her own childhood, but also on the dying days of the writers Susan Sontag, Sigmund Freud, John Updike, Dylan Thomas, Maurice Sendak, and James Salter — all writers, with the exception of Salter, that Roiphe has considered before.

Did Roiphe start writing this book about death when she was a child? It’s clear that Roiphe means it in the clichéd way that writers, even good writers, often do: “the book wrote me” or “I was working on it before I realized it” — it’s the same reason there is more than one novel titled The Book of Memory. But as a once sickly child (and now sicker adult), I can say, as I rarely do, from my own experience, that illness has a way of dissolving beginnings from memory, of blighting projects, of confusing thought rather than concentrating it on a point, light or dark. “Disease was the most basic ground,” the poet Heinrich Heine wrote, “of my creative urge and stress; / Creating, I could convalesce, / Creating, I again grew sound.” This conclusion, whether it ties off neatly or not, is one that comes in adulthood and not earlier.

Still, I almost believe Roiphe, if only because the experience is rendered in a form that the book will take throughout, one that suggests trauma. The prologue is written in a series of vignettes, of flashes; again, many are written in a literary present, some are provocative, like this one about Roiphe’s reading habits as a sick child:

In the meantime, I am reading strange books. I am reading exclusively books about genocide: Primo Levi, Elie Wiesel, firsthand accounts of the Armenian genocide. I have a great, endless appetite for these books, not just for people dying but people dying in great numbers, including children, wars, massacres, naked bodies in trenches. I read them one after another. I am reading with something like desire. I want to see children die.

That the disturbing frankness of this passage is protected by its childhood presentism, I think, bears Roiphe’s imprimatur. It is a strange and even outrageous thing to write: if Donald Trump now wrote that he read books about the Holocaust hoping to see “children die,” there might be a real intervention instead of a pretend one. Yet it will be more alarming for new readers than old ones; Roiphe has pitched herself in the past as a paradoxically ultra-sincere literary shock jock, a writer who accidentally courts outrage by refusing to police herself, as when she famously cut down the claims of rape victims through her written “impressions” (rather than diligent reporting).

Still, Roiphe’s claim works for me because her clipped, vignetted style seems like a (subconscious) way of approaching death slantwise. She appears more afraid than she lets on. The book’s form compares to a repetitive, indirect, and literary version of Tarkovsky’s Mirror, which is to say that it doesn’t work; film possesses a more death-like relation to present and past, and if you’re going to stunt and fragment them, it’s more convincing to render delirious, deathbed remembrances in images — as Elaine Scarry points out, the body in pain has a way of undoing language. But all of this is to say that Roiphe’s approach works in spite of itself; it gives up the ghost of her frankness. “I don’t believe you can learn how to die, or gain wisdom, or prepare and the work I have done on this book has, if anything, confirmed that suspicion,” Roiphe writes in the prologue, “but I do think you can look at a death and be less afraid.” I’m not so sure.

Or maybe it’s not a fear of death, but the human modesty that arises when we handle the deaths of others, especially those we respect, with intimacy. This may account for why The Violet Hour is Roiphe’s least controversial and best book to date (or at least since Uncommon Arrangements), which is also to say that it’s among her most researched works; in order to uncover the deaths of these famous writers, Roiphe intervened in their personal lives. Not only did she dig into archival material, she interviewed family members, which sometimes led to anger or tears.

This approach is particularly rich in the case of Susan Sontag, whose tendency to theorize death and illness clashes with her violet hour needs. She did not want to die, Roiphe makes clear, and (to add to Sontag’s catalogue of self-mythologies) she extends her will almost as far. (“If there is anyone on earth who could decide not to die it would be Susan Sontag.”) It’s here, too, that the vignetted literary present, punctuated by occasional postmortem philosophizing, achieves its purest rhythm. Sontag’s fierce will, in her final days with friends and family, gives way to the ebb and flow of medicated death. Roiphe manages to universalize the particular of Sontag’s dying. “There are drugs to put her to sleep and drugs to wake her up,” she writes, “drugs for the pain and drugs for anxiety.”

For Freud, in the second and second strongest chapter, this anxiety about death should be practiced and mastered. He is pitched as an instructor of death; Roiphe describes him as a thinker who implores us to prepare for it — even as he “overprepares.” Whereas Sontag is described as an indirect communicator of death, even to the point of waylaying meaningful conversations she could have had with her son, Freud is said to approach it with directness, to name it (“he called his own fear of death his “death deliria”). His “sins” and vices, for example his suicidal cigar smoking, become a formulation of his libidinal drive. “[T]he organism wishes to die only its own fashion,” Freud wrote, no doubt while smoking. But in private, in confidence, he could hardly abide death.

If the chapters on Freud and Sontag capture the paradoxes of what C.K. Williams called “writing dying,” the chapters on John Updike and Dylan Thomas blur them with pathos (in the case of the former) and mystery. It takes some stoicism to theorize death, directly or indirectly, but when Updike is told that he has “a year or at least some quality months” to live, he begins to weep. In these sections, The Violet Hour reveals itself as something other than a work of literary criticism; one doesn’t have to be a writer to have a sad or mysterious death, and the collection of any given person’s statements about death, during their life, can always contradict the way they die, no matter who they are. This is to say that the chapter on Updike is mired in a low-grade critical observations about his writing: that he saw adultery or cheating as a way of neutralizing death, however temporarily. And Roiphe’s intercession into the life of Dylan Thomas feels like a BBC documentary about one of the most famous deaths in literature. Was it a suicide?

Still, The Violet Hour regains its force in the final two chapters. The first of these, on Maurice Sendak, justifies the book’s prologue by showing how childhood trauma transmogrify into a lifelong orientation toward death and its images. (Sendak was an adult atheist who saw angels as a sick child.) In an epilogue that is interrupted by James Salter’s unexpected death, the great writer compels Roiphe to “absolute clarity” with regard to her subject. There will be readers of The Violet Hour who come to it for this clarity, and they will get it, like a deathbed painkiller, in doses. Writing dying, it seems, is always a work in progress: each chapter of the book is fronted with an image of its writer’s desk. It ends with Roiphe’s own.