By Jon Bradshaw
Vanity Fair
March, 1985

When Libby Holman arrived in Manhattan in 1924, it was a bold and brassy town, devoted to the pleasure of pleasing itself. Prohibition—“the Great Foolishness,” as the gossip columnist Lucius Beebe called it—was in effect, but it had turned out to be practically unenforceable. With 32,000 speakeasies in New York, the Dry Decade was a glittering time, an era of hot jazz and gaudy pleasure domes, of Model T’s and ticker-tape parades, of flagpole sitters and Ziegfeld girls and sugar daddies, of lurid tabloids and intimate revues, of rouged knees and beesting lips. Rhapsodies were blue, the beautiful were damned, and gentlemen preferred blondes. Seriousness was unacceptable. Oh! Boy. Let’s Do It. Ain’t We Got Fun.

Those song titles could easily have been Libby Holman’s mottoes the day she left Ohio for New York, a twenty-year-old with a low and peculiar singing voice who was looking for a stage career. She had graduated from the University of Cincinnati the year before, and she claimed that college had bored her, that she had learned more from her erudite father than she had learned in all her years at school. “I studied Emerson and Wilde and Jung before I got the curse,” she said.

Libby stood five feet six and weighed 124 pounds. She possessed an ample, almost buxom figure, and she bobbed her unruly raven hair. She was nearsighted, and her weak chin embarrassed her, as did her odd, abbreviated teeth, which seemed too small for her mouth. As one friend said, “Libby looked as though she’d been chewing on moccasins all her life.” Her complexion was a dark, lustrous olive, which caused enemies to snicker and insinuate that she had Moorish blood. She didn’t, of course, but there was something of the gypsy in her reckless temperament and her uncheckable enthusiasms. She was unpardonably seductive, so much so that another friend surmised that she must have been accustomed to lecherous looks from the time she was a little girl. Most of all, she was unashamedly ambitious. Before leaving Cincinnati, she told people that she was going to become a star and marry a millionaire. Although fame and luxury were alien to Libby, they were never far from her mind.

At the end of a year in New York, she was disconsolate and broke, but in early 1925 her “potluck,” as she called it, changed. She landed a part in the chorus of The Garrick Gaieties, a musical by Richard Rodgers and Lorenz Hart, which Robert Benchley called “the most civilized show in town.” It ran for 211 performances, and because of it Libby became, if only by association at first, a minor celebrity. The cast were the pets of New York, both of the Old Guard and of the nascent “cafe society,” and soon Libby was to be seen everywhere, usually surrounded by a cadre of young Princetonians, who escorted her to a string of parties that summer: intimate parties where Richard Rodgers played the piano and Larry Hart did Al Jolson imitations; Algonquin parties where she cracked jokes with Robert Benchley and Dorothy Parker; Sunday-night parties at the Gershwins’; British parties thrown by Bea Lillie and Gertrude Lawrence in the duplex they shared on the West Side; society parties at estates in Westport and Sands Point; and weekend parties at the Boissevain home in Jamaica Estates, where she met Peter Arno and Edna St. Vincent Millay. Libby was the life of all of them, with her crazy energy and her wicked foul mouth, which once provoked Dorothy Parker to remark, “Darling, you really ought to wear your drawers around your face,” and caused Noel Coward to say, “Libby’s the chili to my con carne.”

When the parties were over or not in full swing, Libby’s group, wearing chiffon frocks with uneven hems, satin pumps with baby-Louis heels, and bellshaped cloche hats, met their young men under the clock at the Biltmore and went to the Mayfair dances at the Ritz, or shimmied till dawn at the Club Chantee, or listened to Emil Coleman’s orchestra at the Embassy Club. They ferried across the Hudson to Hoboken beer halls with H. L. Mencken and Ernest Boyd. On hot summer nights, they dined on the Astor Roof and then taxied up to Harlem to see Josephine Baker at the Cotton Club, or went at midnight to the Inferno, where the regulars, instead of taking the stairs, slid down a chute, at the bottom of which stood a large black man in a red devil’s suit who caught them and carried them to their tables.

“It was too perfect,” Libby told the actress Erin O’Brien-Moore. “When you’re twenty-one, there’s so much to do and so much time in which to do it. I did almost anything that popped in my head. It was fantastically exhausting. But even then, I wanted more. I wanted more everything forever.”

In the next four years, however, Libby Holman became famous, not as a singing comedienne, but as a sexy singer of sad torch songs—almost as if she were setting the tone for the tragic life that lay ahead of her. She introduced her first big song, “Salt of My Tears,” in a show called Gambols, and in 1929, when she sang “Can’t We Be Friends?” and “Moanin’ Low” in The Little Show, starring Fred Allen and Clifton Webb, she became Broadway’s hottest star. During the summer of 1929, Manhattan columnists alluded to her as “misery chanting” and “the Statue of Libby.” Walter Winchell wrote: “She is the torch singer par excellence—the best of those female troubadours with voices of smoke and tears, who moan and keen love’s labours lost to the rhythm and boom of the Roaring Twenties.”

In 1930 Libby starred on Broadway in Three’s a Crowd, in which she sang “Something to Remember You By” and the torch classic that was to become her signature, “Body and Soul.” She was basking, as she said, “in the luminous, but not unbecoming, light of fame.”

Libby exuded carnality. She was not a good actress, but she used her affectations—the hand on the curtain, the careless dropping of a handkerchief—with considerable dramatic skill, and when she sang of lost love, of misbegotten affairs and broken dreams, she was wholly believable. Her songs sounded like confessions.

Yet Libby had no tortured tales of her own to tell, at least not yet. Her dreams had seemingly been fulfilled. She was successful and favored, and although she had always claimed that “singers don’t have romances, they inspire them,” she had fallen in love with two millionaires at once, one male, one female—Zachary Smith Reynolds, heir to the Reynolds tobacco fortune, and Louisa d’Andelot Carpenter Jenney, the great-great-great-granddaughter of E. I. du Pont de Nemours, founder of the colossal Du Pont empire.

A tall, beautiful strawberry blonde of twenty-two, Louisa was passionate about the theater, and aspired to being a producer. But she was essentially a country girl. She detested cities, traffic, and hotels. She loved to hunt and fish, to drive tractors and bale hay. She was one of the first female masters of hounds in America and one of the first licensed women pilots. Libby was introduced to Louisa by Clifton Webb during the run of The Little Show, and although their affair was troubled, and glutted with arguments and separations, they remained lifelong friends.

“I don’t mean she actually killed all those people. But they were kind of setup, as though their deaths were meant to be”—Tallulah Bankhead

In 1930, during one of their separations, Libby met Smith Reynolds. The shy, melancholy youth was twenty, nearly seven years Libby’s junior. Tall, with high cheekbones, he had a prominent aquiline nose, slanted eyes, and fair hair. There was something enfeebled in his features, some inbred flaw, which gave his face the choked and sulky look of a spoiled boy who had been denied some new extravagance. A typical Reynolds, he was nervous, highstrung, and suffered from sudden flurries of despair. He was obsessed with aviation, and he pursued this and other pleasures doggedly, permitting nothing to intervene between him and the things he wanted. The New York tabloids referred to him as the tobacco prince and reported his comings and goings with tedious regularity. At twenty-eight he would come into his inheritance of $20 million; in the meantime he had an allowance of $50,000 a year.

Following the tour of The Little Show, Smith dispatched flowers and notes to Libby’s dressing room nightly. The young man was wild for Libby’s favor, but she ignored him. When Libby and Louisa went to Florida for the long Easter weekend of 1930, Smith followed them there; and when the tour ended in late June and Libby and Louisa sailed for Europe, Smith waited a week and tagged dutifully after them.

Although Libby was flattered by Smith’s attentions, she found him a little ridiculous. She and Louisa both treated him like an amiable buffoon. Still, he was always there, and soon Clifton Webb had dubbed him Libby’s mascot, or “Smitty, the traveling bear.” But nothing, not even derision, deterred him.

During the run of Three’s a Crowd, Smith continued to ply his blandishments, even more urgently. He told Libby he was deeply in love with her, and he demanded that she end her relationship with Louisa. When he adamantly insisted that Libby marry him, she became angry, telling him that if he continued to act like a rapacious boy, she wouldn’t see him anymore. In a vain attempt to forget her, Smith flew to California, where he drank late and long and inconsolably, and telephoned her almost daily, begging her to change her mind. But Libby had never been seduced by whimpering.

On the other hand, when Smith talked about flying, he became intense and passionate. Then he exhibited an air of recklessness, an urge to perform gallantly in some romantic circumstance, that appealed to Libby. On his return from California, he went to her show almost every night, and always sat in the same seat in the front row on the aisle. Afterward, he would join Libby at Tony’s, the fashionable West Side speakeasy, even though he loathed the place. He loathed Libby’s life-style altogether, especially her theatrical friends—Clifton Webb, Howard Dietz, Bea Lillie, Dorothy Parker, and Tallulah Bankhead—all of whom he found cold and cavalier. They, in turn, found him insipid, inarticulate, an outsider, acknowledging him only when he bought them drinks, and then barely. Smith felt excluded, and Libby’s heart went out to him. She told Tallulah that Smith had ‘‘a kind of secret treasure buried deep inside of him,” and Tallulah, laughing, retorted that Smith’s riches were only too transparent.

Slowly, imperceptibly, Libby’s feelings toward Smith began to change. She was still in love with Louisa, but they had quarreled and Louisa had sailed for Havana aboard her yacht. Left behind, Libby saw more of Smith than she would have ordinarily. One afternoon, when Libby and Tallulah were sunbathing near Libby’s Long Island home, Smith buzzed the beach in his plane and strewed the sand with yellow roses. Tallulah said, ‘‘Something seems to have made a man of the boy, darling; perhaps we’ve misjudged him,” and Libby agreed. She was suddenly moved by Smith’s attentions, by his strident claims that only she could help him realize his unfulfilled desires. Moreover, she was lonely, because Louisa had chosen to remain in Havana for several more weeks. During the autumn of 1931, as she traveled from town to town on the tour of Three’s a Crowd, Smith no longer seemed like such an improbable proposition. He cajoled her, pointing out that America was in the midst of what would almost certainly be a lengthy depression, that theaters were closing, that she was earning only fifty dollars a week, and that if she were sensible she would weather the encroaching storm at home with him in North Carolina. Finally Libby acceded.

On November 26, 1931, they were hastily married by a justice of the peace in Monroe, Michigan, when Three’s a Crowd was in nearby Detroit. Libby gave her name as Elizabeth Holman, her occupation as “at home.” Smith gave his name as Zachary Reynolds, his occupation as “student.” He gave his true age: twenty. Libby, however, concerned about being so much older, gave hers as twenty-five. She was really twenty-seven, but from that day on she would always be two years older than she claimed.

When news of the marriage became public, Libby’s friends were not generous. One fellow actress said Libby had married more out of compassion than love, and Howard Dietz predicted dire results from what he called their irrational knot. The chief critic was Louisa Carpenter Jenney, who was incensed. She believed Libby had been foolish and opportunistic, and said that the marriage would come to a wretched end.

After the marriage Smith became even more possessive. He continued to badger Libby about giving up the theater and, on one occasion, brandishing a .32-caliber Mauser automatic, threatened to shoot himself unless she complied. She finally submitted by agreeing to abandon the stage for a year in order to devote herself completely to him.

The following summer, when Three’s a Crowd closed, Libby and Smith motored down the East Coast to North Carolina and entered the spacious grounds of Reynolda, the thousand-acre estate built by R. J. Reynolds, Smith’s father. From the main gates, Libby could see the private nine-hole golf course, the stables and greenhouses, and, on a wooded rise, the green-gabled, whitecolumned mansion, with a bevy of servants scurrying about the lawn. A few minutes later they pulled up beneath the porte cochere. They were home.

In the beginning Libby loved being the lady of a country manor, but within a month she had become petulant, depleted. She missed New York, the theater, the spirited banter of witty friends; and it did not take long for her to learn that her listless husband had almost no interest in books or the theater or even travel. He exhibited, in fact, a marked desire to be alone. At times, in a high, stuttering voice, he complained that he was keeping Libby from her friends, and that he was unable to make her happy, and that he could not live up to her expectations of him. In these moods, he occasionally took out his Mauser and placed it against his head.

The Mauser was Smith’s talisman. He would often sit by himself in his bedroom firing it out the window. Two years earlier, it had accidentally discharged, almost injuring his friend C. G. Hill. Libby urged him to get rid of it, but Smith insisted that he was a rich man and needed protection.

On Tuesday, July 5, 1932, they threw a party at Reynolda and invited members of some of Winston-Salem’s finest families. As the evening began, Libby was vivacious and talkative, but an odd tension darkened her gaiety. At one point she and one of the guests, Babe Vaught, engaged in an impromptu drinking contest, and before the party was an hour old it was obvious to everyone that both women were drunk.

Shortly before nine o’clock, Libby disappeared; and no one saw her for the next three hours. At eleven the guests began to leave, and by midnight only Smith and Ab Walker, his best friend, and actress Blanche Yurka, a houseguest of Libby’s, remained in the house. At 12:30 Libby reappeared and Smith escorted her upstairs. Ab Walker remained below, but he could hear them arguing. A few minutes later the night watchman, outside on the lawn, heard what sounded like a gunshot, but he was unable to discern from which part of the house it had come. He heard nothing more, and thought no more of it.

Blanche Yurka, who had been asleep, was then wakened by what sounded like Libby in hysterics. She walked out onto the gallery which surrounded the living room and, seeing Walker below, said she thought she had heard someone scream. At that moment, Libby cried out again, quite loudly, “Ab! Ab! Ab!” Ab rushed up the stairs and Libby lurched toward him from her bedroom. When she reached him, she whispered, “Smith … Smith shot himself.”

Smith was lying on their bed. He was unconscious, and blood seeped from a wound in his head. Libby, Ab, and Blanche Yurka carried him down to Libby’s car and drove to Baptist Hospital in Winston-Salem, where four hours later the young millionaire died without having regained consciousness.

The Smith Reynolds tragedy became the American scandal of 1932. The New York Daily Mirror, attempting to shore up its sagging circulation, published a twenty-seven-part series on Libby, accusing her of wearing mannish attire, of being a heavy drinker and attending mad midnight revels, of being a sensual sex pirate, a red-hot mama, an iceberg of disdain. The first installment ended: “As a little Cinderella out of the Middle West, she captivated Prince Charming, but their fairy tale of romance was blighted by murder—or was it suicide? It’s a thriller. Don’t miss it.”

The Reynolds family insisted that Smith had committed suicide, but everyone else in North Carolina seemed to feel that Libby had murdered him, possibly with the assistance of Ab Walker. It would take more than four months to unravel what the newspapers had begun to call “the mysterious death of Smith Reynolds.” A coroner’s inquest was held at Reynolda, and everyone who had been there the night of the death was called to testify. Almost all of them lied, claiming that Libby and Smith had been perfectly happy, that no one had drunk to excess, and that the party had been tame and ordinary.

Ab Walker, who prior to the inquest had told a friend that there was a secret concerning Smith’s death that he would carry to his grave, now denied ever having made the statement and insisted he had been little more than an innocent bystander. But the most shocking revelation came from Libby. She claimed that she hadn’t been drunk, and that, moreover, the shock of Smith’s death had triggered a profound though temporary form of amnesia; she said she remembered absolutely nothing of the party or of the incidents surrounding the tragedy. “It wasn’t a mental picture of anything particularly clear after the flash of the gun,” she said, “but I have this feeling that Smitty was in my arms and I felt this blood, but it is a haze, it is blurred.” That was all the prosecutor ever got from her. Even so, Libby and Ab were held as material witnesses.

From the beginning, the investigation into Smith’s death was blundering, incompetent. The fatal bullet was never found, and it turned out that although Reynolda employees had made three searches of the sleeping porch where Smith had been shot without finding the gun, on the fourth search the weapon was discovered in plain sight in the middle of the room. Clearly, someone had removed and then replaced the gun, which was so smudged that fingerprinting was impossible. Also, it was never determined whether there had been powder bums on Smith’s forehead, or where Libby had gone during the party, or what the secret was that Ab Walker intended to take to his grave. Libby continued to insist that she was suffering from amnesia, and in the end the coroner’s jury concluded that Smith had met his death “from a bullet wound inflicted by a party or parties unknown.” The vagueness of the verdict legally excluded Smith Reynolds from being the unknown person but also freed Libby and Ab Walker as material witnesses.

Less than a month later, however, a grand jury was formed in Winston-Salem to investigate the Reynolds case, and on August 4, 1932, it produced an indictment: “that Albert Walker and Libby Holman Reynolds did unlawfully, willfully, feloniously and premeditatedly of malice or aforethought kill and murder Z. Smith Reynolds.” Ab Walker was arrested immediately, but Libby had disappeared, and the combined police forces of North Carolina, Ohio, Maryland, and Delaware were unable to find her. Louisa Carpenter was hiding her on one of her estates in the northern Chesapeake Bay area.

The next day Alfred Holman, Libby’s father, announced that Libby, who had claimed at the coroner’s inquest that Smith was impotent and that he had urged her to have an affair with another man, was two months pregnant with the heir to the Reynolds tobacco fortune. Holman knew the revelation would shock the Reynolds family, who were loath to part with Smith’s estate.

Libby was distraught, convinced that she was responsible for the tragedies around her. She thought of herself as a kind of medium, a conduit through which death radiated to others.

A few days later, Libby turned herself in. The North Carolina state solicitor decided that the state did not possess sufficient evidence to support a charge of premeditation, and Libby and Ab were released on bail. In the end the case never came to trial, primarily because Will Reynolds, Smith’s uncle and chairman of the executive committee of the Reynolds Tobacco Company, intervened. In a letter to the state solicitor, Reynolds urged him to drop the case on the grounds that his family would not “find any pleasure in a prosecution not fully justified by the circumstances of [Smith’s] death.” In his view, there had already been too much publicity and scandal, too much squalid talk of suicide, shooting, drinking, and impotence, and none of it would bring Smith back. Eventually the state solicitor issued a nolle prosequi with leave, meaning that the case was closed but could be reopened at any time. On November 15 Libby and Ab Walker were set free.

But it was not over. The death of Smith Reynolds would haunt Libby for the rest of her days. Like some mysterious, untreatable disease, it would infect her life and her career, and almost everyone who came to know her—friends, acquaintances, new husbands, lovers— proved to be more than passingly curious to find out what had actually happened on that summer night in 1932.

Libby remembered more than she had admitted to, of course, but not much more. She had been drunk that night, and for Libby a surfeit of alcohol invariably led to at least a partial loss of memory. Many years later, following another night of prodigious intoxication, Libby said to her drinking companions, “Now, tell me what we did last night. I can’t remember anything. And don’t spare me. I want it blow by blow, word for word.’’

The morning Smith died at Baptist Hospital, Libby returned to Reynolda, and the Reynolds family physician told reporters that she was prostrate with grief, that she had been given a heavy sedative, and that she would not be able to talk with them, or with anyone, not even the county sheriff. But upstairs, alone in her bedroom, Libby was wideawake. She telephoned her parents in Cincinnati. She called her friends Howard Dietz and Clifton Webb in New York, and Louisa Carpenter Jenney in Delaware. She told Louisa that the Reynolds family were being horrible to her, almost as if they suspected she had had something to do with Smith’s demise. But she maintained that she could not remember anything. “I was so drunk last night,’’ she said, “I don’t know whether I shot him or not.”

It is one thing to have known what happened and lied; the deeper tragedy is not to have known at all. For the rest of her life, Libby wondered whether or not she had shot Smith Reynolds. It would have been unlike her, because she was not inclined to violence; nevertheless, her husband was dead, and all she could remember was the sound of her name, a crash, and the warm blood.

For Libby, Smith Reynolds’s death was a point of no return—beyond which lay a future she would not otherwise have had. It had altered everything, but she didn’t know that then. Nearly a lifetime would pass before Libby, looking back, could isolate that tragic moment and confide to a friend, ”There, it was there the detour began.”

On January 10, 1933, Libby gave birth prematurely to a three-and-a-half pound boy, whom she named Christopher Smith Reynolds. Then the battle for his father’s estate began, and it was not until March 15, 1935, that it was settled. Libby received $750,000 for herself, and her child inherited $6,250,000. Libby was overjoyed; she was rich as she had always wished to be. But her career was in ruins, and from that time on, almost every man she touched died violently.

For the next few years, Libby and Louisa Carpenter Jenney lived together with Christopher, or Topper, as Libby called him, and with Sunny, Louisa’s adopted daughter, at Louisa’s estate in Montchanin, a suburb of Wilmington. In 1934 the Philadelphia Evening Bulletin announced that “the slumber-eyed, raven-haired, petulant-lipped, husky-voiced” Libby Holman was returning to Broadway. Libby felt she had been in retirement long enough, that the Smith Reynolds tragedy was at last behind her, and she confirmed reports that she would appear in Howard Dietz and Arthur Schwartz’s new musical, Revenge with Music. When the show opened on Broadway in November 1934, the reviews were dire, and during the opening-night intermission a woman in the lobby was heard to say, “I bet she killed him. I just bet she killed him.” Libby’s hit song, “You and the Night and the Music,” was temporarily banned on the radio because it was considered risque, a fact that only served to bolster her already notorious reputation.

The following year MGM released a film entitled Reckless, which was obviously based on the Smith Reynolds case. Libby was outraged and threatened to sue, but instead she retreated to Montchanin with Louisa and Topper.

In 1936 Libby met an actor named Phillips Holmes, and they began a love affair that lasted two years—”a limited engagement,” as Louisa called it. Holmes fulfilled many of Libby’s criteria: he was not rich, but he was five years her junior, pliant, and beautiful, and he had briefly attended Princeton. Phillips seemed too good to be true, and, in the end, he was. They quarreled increasingly. Phillips did not understand Libby’s outbursts, her venomous denunciations, nor did he seem to realize that this strong, tyrannical woman was attracted to subservient men whose weakness she initially exploited and ultimately found unforgivable. During the late spring of 1938, she ordered Phillips from her home. He was devastated, but Libby felt no regret and offered little explanation for her change of heart. She certainly didn’t mention that during his long absences, when he was filming in London or Hollywood, she had been seeing his younger brother, Ralph, or Rafe, as she called him.

Rafe Holmes, an actor like his brother, was twenty-three, eleven years younger than Libby, and she referred to him as “the sexiest man on both sides of town.” On March 27, 1939, they were married secretly and honeymooned at Treetops, a fifty-five-acre estate between Stamford and Greenwich, Connecticut, which Libby had purchased the year before, and on which she had built a vast neo-Georgian house as “a suitable and attractive home for Topper.”

During the summer of 1940, Ralph and Phillips, who were half-Canadian, joined the Royal Canadian Air Force. Two years later Phillips passed his R.C.A.F. flying examination and, thinking he would be posted to the European front immediately, telephoned Libby to say goodbye. The maid informed him that Mrs. Reynolds was not receiving calls that evening. On the afternoon of August 12, 1942, shortly after taking off from Armstrong, Ontario, the military plane in which Phillips was a passenger collided with another aircraft. There were no survivors. Phillips was thirty-three.

Rafe spent three years in Canada training pilots and was then dispatched to England, where he spent the next fifteen months. Desperate to see action, he transferred to the American armed forces and flew bombing missions over Germany. Libby had seen him infrequently while he was in Canada, and for the last two years of the war she did not see him at all.

Shortly after V-J Day in 1945, Rafe returned home, suffering from battle fatigue. He intended to give up acting in order to enter Wall Street or politics, and he received several business offers, but he accepted none of them. Instead he brooded and began to drink as much as a fifth of scotch a day. He took eight to ten sleeping pills a night and rarely rose before early afternoon. He got fat, and Libby became irritable around him. They rarely made love; Rafe was usually too tired, or too distracted, or too drunk. Libby was not sympathetic. Paraphrasing a remark of Clara Bow’s, she told a friend, “Poor Rafe. He’s got the biggest cock in Connecticut, but no ass to push it with.”

Libby finally ordered Rafe from Treetops. Six weeks later his body was found in his Manhattan apartment. He had been dead for five or six days. The New York medical examiner revealed that the twenty-nine-year-old had died of barbiturate poisoning, but no one knew whether the overdose had been deliberate or accidental. Libby was forty-one, and her second marriage had ended as unnaturally as her first. When Hassard Short, the lighting designer, heard of Rafe’s death, he said, ”Well, Libby certainly seems to be in a rut.”

That winter and the following year, Libby entertained a variety of friends at Treetops. These friends were a close clique of loyal fans and included director Bobby Lewis, dancer Paul Godkin, lyricist John LaTouche, set designer Oliver Smith, British director Peter Glenville, writers Jane and Paul Bowles, and, occasionally, the fledgling dramatist Tennessee Williams. While Topper was away at prep school, Libby, with her son’s approval, adopted two boys, Timmy in 1945 and Tony in 1947, and so Treetops was glutted with guests and governesses and a permanent staff of five.

In June 1950, Topper graduated from the Putney School. Before entering Dartmouth that fall, he decided to spend the summer in California working at a silver mine. For years, the seventeen year-old youth had been obsessed with mountain climbing, and he determined with a friend to scale Mount Whitney in order, as he said, “to challenge the gods, to chart the unknown.”

On August 6, Topper and his friend began their ascent, and two days later, when they were eight hundred feet from the top, they both fell to their death. Libby never saw Topper’s body, but his death was her crucifixion. She had always believed that he would do something splendid with his life, that he would have a bright and singular destiny, “but not this,” she cried, “any-thing but this.”

Libby had taken a photograph of Topper a few months earlier; it was her favorite likeness of him, and she hung it in the foyer outside her bedroom next to photographs of Smith Reynolds and Phillips and Ralph Holmes. She referred bitterly to the pictures as “the gallery of all my romantic homicides.”

In 1952, in memory of her son, Libby created the Christopher Reynolds Foundation, which contributed more than $3 million to civil-rights causes, universities, hospitals, institutes, refugee relief, and community-relations programs. Libby considered it her proudest achievement, and of all the endowments the foundation awarded, she was most pleased with one she had given in 1959 to Dr. Martin Luther King, Jr., who was emerging as the leader of the civil rights movement. King greatly admired Mahatma Gandhi and wished to visit India in order to talk with those of Gandhi’s associates who were still alive, and when Libby learned of King’s wish, she instructed the foundation to award a $5,000 grant for his use. King was grateful to Libby for her help, and he and his wife and Libby became friends.

During the early ’50s, Libby became involved with the actor Montgomery Clift. An alcoholic and a homosexual, Clift was seventeen years younger than Libby, but she considered him the grand love of her life, and although her closest friends thought the relationship bizarre, it lasted fitfully for nearly ten years. They were devoted to each other, in their zany and preposterous way, lovers who often seemed like accomplices committed to pulling off a romantic swindle just to prove that it could be done.

Despite the tragedies of Libby’s early life, her last fifteen years were, in many ways, her darkest period. After suffering from ulcers for a number of years, she finally underwent surgery and had seven-eighths of her stomach removed. She was also manic-depressive, and the older she got, the more profound her “glooms” became. She began to refer to herself as “the Master of Melancholy.” In 1959, to the astonishment of her friends, she married Louis Schanker, an abstract-expressionist painter, and for Libby this was a romantic debut of sorts: Schanker was not young or gay or Gentile or pretty.

Louisa Carpenter Jenney called Schanker “the hairy parvenu,” and Paul Bowles said he was a gruff, illtempered man who treated Libby abominably. Gradually, her old friends began to feel that they were unwelcome at Treetops. Libby never discussed her marriage openly, but after 1963 her depressions deepened. Only her employees knew that the marriage was a torment to her. Whenever anyone asked William Hill, Libby’s Scottish butler, about her, or her past, or the death of Smith Reynolds, he would say, “I don’t know whether she killed Smith Reynolds or not, but the husband she ought to kill is Louis Schanker.”

As the rebellious voices of the ’60s became more strident, Libby felt a growing sense of alienation. She seemed muddled, adrift, teetering precariously between absurd extremes. When a friend advised her not to worry about a thing, Libby replied, “I don’t. It’s everything.” In a span of less than five years, those who had once been Libby’s intimates began to die, one after the other—Lucius Beebe, Clifton Webb, Tallulah Bankhead, Josh White. On July 23, 1966, Monty Clift died in his sleep at forty-five. His death was officially diagnosed as occlusive-coronary-artery disease, but a friend may have been more accurate in calling it the longest suicide in history. On April 4, 1968, Martin Luther King, Jr., was assassinated. Some months before, Libby had written to him, “There are no words that I have to express to you the gratefulness in my heart that you exist.” And now he too was gone.

Libby was distraught, convinced that she was responsible for the tragedies around her. She thought of herself as a kind of medium, a conduit through which death radiated to others. And there was something else. Martin and Monty had seemed so much more fortunate than she. And yet they had achieved surcease of pain, deliverance, while she remained behind—compelled to soldier on, to suffer, to endure.

On Friday, June 18, 1971, at Treetops, in the front seat of her RollsRoyce, Libby Holman committed suicide, dying from carbon monoxide poisoning. She was sixty-seven. Her estate was valued at $13,200,000, the bulk of which was donated to the Christopher Reynolds Foundation.

Tragedy had shadowed Libby from the start, had shaped and colored all her dreams, and it was not to end with her death. On May 4, 1973, her dear friend Jane Bowles, who had lost her sight, her speech, and her sanity, died a hopeless schizophrenic at the Clinica del Los Angeles in Malaga. She was fifty-six and was buried by her husband, Paul, in an unmarked grave. On February 8, 1976, her best friend, Louisa Carpenter Jenney, crashed in her private plane outside of Wilmington. She was sixty-eight. There were those who, although horrified, liked to claim that Libby had been a witch after all, that her hand stretched far beyond the grave.

Click here to buy Jon Bradshaw’s biography of Libby Holman, Dreams That Money Can Buy .

[Photo Credit: Maurice Seymour via Wikimedia Commons]

The Notorious Libby Holman