Debt and depression — surely these demons don’t haunt writers any more than they do the rest of the population, but it falls to writers to describe the experience of poverty or melancholy in ways that bankers or doctors never will. That becoming a writer requires something alternately called confidence or courage or self-delusion lends the sting of penury extra venom and makes the paralysis of depression all the more existential. If you can command words on a page that editors want to publish, why is your bank account empty? If your name is on the cover of books people buy in shops, why can’t you get out of bed in the morning?

Lee Siegel and Daphne Merkin were both born in the 1950s, grew up about 20 miles away from each other, and became two of the most dynamic intellectuals of their generation. Both of them marched through the pages of America’s big little magazines — particularly the back pages of The New Republic — issuing judgments with a wit and grace that have all but gone out of style. Merkin belongs to the genteel, Olympian school of New York intellectuals whose thunderbolts fall with the force of a thousand library stacks. Siegel is more of a street fighter, his jabs pretty lethal. Both have now published memoirs of their struggles with their respective black dogs: debt for Siegel in The Draw; depression for Merkin in This Close to Happy. As far as what the two books have in common, we know what Philip Larkin said Mum and Dad do to you, but this hasn’t prevented Siegel and Merkin from having kids of their own or crafting stunning self-portraits out of their miseries.

It would be a step too far to call these memoirs shadow works of criticism. Merkin’s book is an essay turning over the question of why she sometimes wants to kill herself. Siegel’s tells the story of how he became what he is, a critic. Both books are haunted by other, unwritten books. Merkin cites “that Ur-document of unfulfilled creative talent,” Cyril Connolly’s 1938 hybrid of criticism and memoir, Enemies of Promise. (One of those enemies is book reviewing.) But Merkin and Siegel grew up in what counts as a golden age of criticism — Wilson, Fiedler, Hardwick, Kenner — and came to occupy enviable perches in what seemed a diminished field, which then seemed to diminish further. But just as the novel is always dying, the literary sky is always falling, and yesterday’s wunderkind critics go on to become middle-aged memoirists reviewed by those who showed up after everything was supposedly already over.

Merkin’s book is a mystery story: She’s had “the hypes, the blues, the mean reds” long enough to see all the theories — psychological, environmental, biochemical, genetic, etc. — come and go without a diagnostic smoking gun appearing, much less a surefire remedy. She suspects all along that it’s something to do with her mother, who was never present enough. Merkin’s parents were Jews who fled Germany in the 1930s. Her father made a fortune on Wall Street, was a prominent philanthropist, and, Merkin says, never took an interest in her. Their apartment on the Upper East Side was large, but not so big that the six siblings didn’t have to share rooms or that it didn’t feel like a prison. There was never enough fruit around, and it tended to come in cans because her mother didn’t like to go to the grocery store. We see Merkin as a child at night slipping a note to her mother under her parents’ bedroom door: “I can’t fall asleep. Need to talk to you. Will only take a few minutes, I promise.”

After her mother dies, Merkin’s sister tells her that among the papers she threw away from their mother’s desk was a note that read “Daphne is just like me.” But even this is no explanation; despite her siblings’ travails, she never fully accepts that it’s genes that bring on what she calls her dark seasons. The mystery lies between her mother’s being “one of the most vivid people I’ve ever met,” the tender side revealed when singing lullabies, and a stifling tendency that was far stronger. As Merkin puts it when delivering her eulogy, “Daphne, I can almost hear her say, speak slowly and clearly. And remember: no one wants to hear another word about your childhood.” How painful to have your mother (and great subject — Merkin portrayed her in the autobiographical Enchantment) tell you not to do what you were obviously born to do.

Siegel’s book is anything but a mystery. He knows exactly what happened and why. The Draw is a mock-heroic picaresque, concluding when young Lee — now in his early 20s, an avid reader of books, a frustrated writer of fiction, a serial defaulter on debts, and someone clearly unfit for the odd jobs in retail that keep him afloat — secures a loan to enroll at Columbia. (Siegel has written elsewhere about defaulting on this loan and others too.) Debt was a curse he inherited; it was his parents’ fates he was always trying to escape. His mother, Lola, was an aspiring actress who studied at the Actors Studio alongside Marlon Brando. She once asked Brando why he didn’t wear nicer clothes to class, instead coming in jeans and a T-shirt like Stanley Kowalski. “Fuck you,” he told her. Lola fell in love with Monroe Siegel, a Korean War veteran and jazz pianist who gigged around town. She married him against the wishes of her father, a Russian Jew who settled in the Bronx and worked as a bellhop at a Times Square hotel preferred by performers playing in Harlem. The actress and the pianist gave up on their dreams and bought a split-level house in Paramus. He became a Realtor, she a housewife and substitute teacher. They never got over it.

Siegel tracks his father’s floundering in real estate and marriage to monetary policy of the early 1970s. “Interest rates went up,” he writes. “Male erections came down. Women who depended on men for pleasure and procreation went unfulfilled. The fate of tens of millions of men and women hung in the balance as President Nixon tried to persuade his chairman of the Fed to substantially lower interest rates.” There’s surely some comic exaggeration at work here, but Monroe’s business did dry up even as he continued on “the Draw” — his firm’s way of advancing agents money against future sales. By the time he was fired he was $50,000 in debt. His employer referred the debt to the county sheriff, who came to lay claim to his house. Monroe was also impotent and sleeping on the couch. Lola divorced him and got the deed to the home. Bankrupt, Monroe rented a small room nearby, gave piano lessons, and went on welfare. Lola in middle age came unhinged, and mother-son relations took on an unwelcome erotic tinge.

It was under this cloud that Siegel made his way through Bradley College and Montclair State, working as a short-order cook, gas-station attendant, and shoe salesman — dreary pursuits that tended to end when, thinking of himself as a Brando in disguise, he told his bosses to go fuck themselves. Here is a portrait of the writer, a box of unpublished short stories sitting in the basement, age 20: “I had always been angry, but for the first time I was aware of being angry. I could sit at my mother’s kitchen table and eat a whole seven-layer Pepperidge Farm cake without realizing it. As I chewed, my heart pounded and my head whirred with memories of slights received. I brooded on fantasies of revenge against people who had treated me not like the boy who suffered for his offbeat merit, or the boy who could read a book like nobody’s business, but like a loser who was lucky to get what he had.”

Siegel’s bitterness has served him well over the years, no doubt a source of the sparks that have provided constant ignition to his career as a critic. The Draw is the book he was born to write. It comes after years of lavishing his attentions, hostile or otherwise, on other writers and artists living and dead. At last, Lee-boy, as his father called him, is the hero. And lurking beneath the story of his debts, Siegel has smuggled in another book, about sex, that flaunts his reading of his heroes — Mailer, Bellow, and Roth. Merkin operates under their spell as well. In her fiction and essays — she’s of course famous for confessing to a taste for erotic spanking in the pages of The New Yorker — she’s long pursued an autobiographical impulse, but This Close to Happy took her more than a decade (and three publishers) to write. It wasn’t simple for these children of the baby-boom, both of whom spent too much time as children reading about the Holocaust, to figure out how to tell the worst stories about themselves. They both know that the mirror is the place to be merciless.

*This article appears in the April 3, 2017, issue of New York Magazine.