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Patricia Highsmith Was Almost as Twisted as Tom Ripley

Vanity Fair / April 2024

The iconic author’s diaries and biographies reveal that the devious Highsmith had a lot in common with her infamous character

“Writing, of course, is a substitute for the life I cannot live,” Patricia Highsmith wrote in a diary entry from 1950. Were she Jane Austen or a Brontë sister, this might be a romantic statement. But coming from the creator of Tom Ripley—arguably literature’s foremost psychopath—such a sentiment is dark and disturbing.

What kind of person could conjure the deceptive, duplicitous, sociopathic, murderous, albeit talented, Mr. Ripley? And how did Highsmith’s own notoriously nasty, miserable, and misanthropic personality compare to that of her most indelible character? As Netflix brings another reincarnation of the queer, killer con artist to the screen—in Ripley, which premieres April 4—we take a peek into the strange mind that created a criminal alter ego in Tom Ripley.

An insurmountable, quasi-incestuous upbringing

Born in 1921 in Fort Worth, Texas, Highsmith was the unwanted child of an absent father and a resentful mother whose DIY turpentine abortion had failed. She remarried when her only daughter was three. By eight, Highsmith loathed the union so much that she later wrote “evil thoughts of murder of my stepfather”—whom she thought was her biological father at the time—were commonplace.

Mother and daughter had a lifelong complicated, competitive, and dysfunctional relationship. “Neither woman could distinguish herself from the other,” wrote biographer Joan Schenkar, author of The Talented Miss Highsmith. Patrica saw her mother, a failed artist, as a realization of her deepest fear; meanwhile, narcissistic Mary was jealous of her daughter’s literary success and intimate relationships with other women. “Pat wanted Mary to admit that she alone was responsible for the dreadful ‘abnormality’ of her daughter’s sexuality; Mary refused to do so,” wrote the recently deceased Schenkar. A 29-page letter that Mary wrote to Patricia called her a compulsive liar, sadist, and pervert. (Orphaned Tom Ripley is similarly tortured by his Aunt Dottie’s snide letters that taunt him, calling him a “sissy.”)

Incapable of either getting along or leaving each other alone, the Highsmiths’ mother-daughter folie à deux was, as Schenkar put it, “The real love that could not say its name.” Everything that Patricia could not say aloud, however, went into her diaries. In an entry written at age 20, she considered, “Could I possibly be in love with my own mother? Perhaps in some incredible way I am.”

Eight thousand pages of maybe-true confessions

The above entry is but one of 8,000 scribbled pages found in 56 hidden notebooks (or, Highsmith’s preferred word, cahiers) discovered posthumously by her editor, Anna von Planta. “I thought: Where would I find something so personal, so intimate, that only the right person would find it? Behind my clean sheets and tablecloths, I thought, and indeed, there they were,” von Planta told Vanity Fair.

Beginning at 15 years old, Highsmith wrote often and fervently of life’s minutiae—cataloging the books she read, what she learned at school, poems, dreams, gossip, and random observations. She borrowed from the diaries for her fiction, and vice versa elevated her diaries with fabrications. “Like [in] many diaries,” says von Planta, “she often wrote less about the ‘real’ Pat, but rather the person she wanted herself to be.” The volumes contained vivid descriptions of people who may not have existed and events that may have been entirely made up, such as a supposed years-long lesbian affair beginning in 1938 with a “Virginia” that is unknown to Highsmith’s closest friends and unconfirmable by her biographers.

While “neither glossing over nor interpreting anything,” says von Planta, Highsmith meticulously transcribed and edited the pages that form the book, Patricia Highsmith: Her Diaries and Notebooks, 1941–1995. And yet how much of Highsmith’s cahiers were imagined, embellished, or projected is ultimately unknowable. Like Ripley, inventing reality came all too easy to the uncommonly talented Highsmith: “Honesty, for me, is usually the worst policy imaginable,” she once wrote.

She resented the elite—and desperately wanted to be one of them

Highsmith hailed from a once rich Confederate family whose glory days and money were long gone by the time she arrived. (The 110 slaves her great-grandfather owned, she said in a 1977 interview, were “not unhappy.”) She romanticized both General Robert E. Lee and Gone with the Wind hero Ashley Wilkes—a bad look even in 1938, the year Highsmith enrolled at Columbia’s sister school, Barnard College.

Though she’d earned her spot in the Ivy League, an insecure Highsmith said little about her past while there, as it didn’t at all resemble her classmates’ wealthy, traditional families. But the mediocre student dressed the part—perfecting her signature costume of crisp white shirts and riding clothes, as though she were an equestrian—and mingled in New York literary circles, including those of Tennessee Williams and Truman Capote. If Highsmith felt as if she’d been invited into the club for a brief spell, post-graduation rejections from Vogue, Good Housekeeping, Mademoiselle, Time, Fortune, and The New Yorker proved otherwise.

After a few years of lowly gigs in the city, the success of Highsmith’s Strangers on a Train brought her enough resources to gallivant Ripley-like across the Old World. “She immediately took to Europe, moving through Paris and Rome and mixing with the upper classes,” says Richard Bradford, author of Devils, Lusts and Strange Desires: The Life of Patricia Highsmith, in an interview with VF. “She wanted to be part of their world, but she always felt like an outsider.”

Volatile affairs “by the dozen” with rich, married women

In the author’s second book, The Price of Salt—a lesbian romance Highsmith originally published under a pseudonym—the sophisticated character Carol embodies Highsmith’s ideal woman: a married heterosexual, preferably older and rich, whom she might lure away from a traditional relationship. This predatory pattern emerged early; at 17, Highsmith wrote that there were “so many girls to choose from,” particularly at her all-female university. “I observe the pickings at Barnard.”

Though she occasionally slept with (usually homosexual) men, Highsmith mostly slept with women—and lots of them. She boasted of having “love affairs by the dozen” and dedicated Strangers on a Train to “all the Virginias,” since she’d slept with so many women by that name. Among a series of overlapping long-term affairs, she had dalliances with married socialite Virginia Kent Catherwood; Ellen Blumenthal Hill, a married sociologist; and Kathryn Hamill Cohen, her publisher’s wife.

Never monogamous and probably a nymphomaniac, Highsmith boasted that she sometimes had 10 different lovers in a day. She’d meet women at gay bars and was known for calling her next lover from the bedroom of her last one. But Highsmith’s particular kink was ménage à trois. As Schenkar wrote, “The geometry of the triangle never lost its appeal.” Highsmith described at least six threesomes in her diary. She would plan the seduction of the unsuspecting couple in advance—although none of them culminated in murder, all ended badly nonetheless.

Highsmith’s relationships usually terminated in “adultery, disclosure and conflict,” writes Bradford. Fuelled by passion and alcohol, a breakup with Ellen Hill was particularly brutal: threatening suicide if Highsmith set out to yet another party, Hill washed a dose of barbiturates down with a martini while Highsmith watched. “Then she left her there, to die, and went off to have sex with at least two other people,” he says. (Hill didn’t die, but she did go into a coma.)

An alcoholic, chain-smoking anorexic

Granted, everyone drank more during the three-martini lunches of the 1940s, but Highsmith nursed a morning-til-night drinking habit beginning in her late teens. (In fact, she twice notes a seven-martini lunch.) She classified drinks not by contents—though those contents preferably included gin—but by the time of day and activity when she imbibed them, including “breakfast drinks,” “walking drinks,” “talking drinks,” “dressing drinks,” and “writing drinks.” In her oversized purse, she always carried a flask.

“Did anyone, after a certain point, ever see Patricia Highsmith sober?” asked Schenkar, who notes that most friends claimed to be unaware the writer was drunk—having never seen her sober. The same was true of Highsmith’s ever-present Camel cigarettes, of which she smoked two packs a day.

As far as consumption, however, that’s about it. Highsmith’s kitchen was stocked with liquor but little else. At five-foot-six, she weighed as little as 103 pounds and never more than 110. As a result, Highsmith suffered from hormone deficiencies, infrequent periods, and cold extremities. All these are symptoms of anorexia, though the condition wasn’t known to Highsmith until she read a 1969 article about the new “slimming sickness.” “I had all these symptoms age 15–19,” she scribbled atop the clipping.

Hidden in her diaries among proud descriptions of copious amounts of gin, are Highsmith’s periodic thoughts about taking “therapeutic measures against alcoholism. Something must be done.” Sadly, nothing was, and Highsmith’s addictions only worsened over time. With them went her looks; though the writer was once considered devastatingly attractive, Highsmith’s face became deeply lined, stained, and jowled. Gargoyle-esque in her small size and poor posture, Schenkar notes the writer was often directed to the men’s bathroom.

A racist, antisemitic, homophobic “equal opportunity offender”

Highsmith died of lung cancer in 1995 at the age of 74, four years after Ripley Under Water became the last book published in her lifetime. The fifth and final installment in the series finds the psychopath living a life that, at least partly, eluded his creator: Ripley is happily married to a rich heiress and living in a small French village, which Highsmith herself did for many years, but alone, and despite her hatred of the French. (For eating snails, her favorite animal, she condemned the French as cannibals, Bradford writes.)

Besides the French, Highsmith hated Blacks, Latinos, Arabs, Koreans, Indians (both South Asian and “Red”), Mexicans, and the Portuguese. She loathed Catholics, evangelicals, and fundamentalists. A friend once called her “an equal opportunity offender.” But Highsmith hated Jews most of all and, perhaps because of the indignation her opinions sparked, was not afraid to say so. She called the Holocaust the “semicaust,” regretting that Hitler had not killed more Jewish people. After her death, her own publisher denounced her to Entertainment Weekly as a “mean, cruel, hard, unlovable, unloving human being.”

Her diaries include many unprintable incidents of racism and antisemitism, but also the uncomfortable fact that many of Highsmith’s lovers, and most all of her actual loves, were Jewish. “She was full of contradictions which defined her and fuelled her writing,” says von Planta. A refusal to differentiate between love and hate or good and evil that lacked any self-awareness is pure Highsmith—and pure Ripley.

Even for a writer whose books were “a lifelong autobiography,” writes Bradford, the unsettlingly likable psychopath Tom Ripley was especially close to Highsmith’s cold, dark heart. The Talented Mr. Ripley is her only undedicated book because Highsmith had already slyly dedicated it to herself: When Tom Ripley signs his real name, his middle initial is P—for Patricia.