Forget The Great Gatsby, Libby Holman was the perfect symbol of 1920s debauchery and decadence. America became obsessed with the sultry performer for her crazy personal life. With countless scandals, affairs, and tragedies, no one could blame them.
1. She Went From Riches to Rags
On May 23, 1904, Elizabeth Lloyd Holman was born to stockbroker Alfred Holman and Rachel Florence Workum Holman. Thanks to mom and dad, Holman was born with a silver spoon in her mouth…until a brutal betrayal ripped it away. In the same year, her uncle embezzled almost $1,000,000 from the family business and fled the country. His wicked greed left a trail of devastation in its wake.
2. An Early Betrayal Changed Her
Just like that, the affluent Holmans went from riches to rags. To salvage his reputation, Libby’s father Alfred even agreed to pay back every cent of the missing funds to investors—even if his daughters paid the price for this. Alfred and Rachel raised their kids in destitution. The betrayal and poverty sparked flames inside Holman.
She never wanted to be poor again. But the youngest Holman didn’t know fame and fortune would cost her dearly.
3. She Was A Gold-Digger
Holman always knew what she wanted: fame, wealth, and a loaded husband. She was an unabashed fortune chaser: it was better to be a naughty gold-digger than broke. Holman recognized she wasn’t going to find what she wanted in Cincinnati. So she left her hometown in search of fame and fortune in New York City—and got way more than she bargained for.
4. Her Dad Didn’t Approve
Alfred never approved of Libby’s ambitions. Instead of glitz and glamor, he dreamed of a white picket fence life for her. It was basically the comfortable life he and Rachel enjoyed until their world turned upside down. He had a feeling the path Libby chose wouldn’t end well. Sadly, he turned out to be completely right. But even Alfred couldn’t have predicted the scandals and tragedies that were in store for her.
5. She Hustled Her Way To The Top
20-year-old Holman made a solo move to the Big Apple with nothing more than some cash, a college degree, and unadulterated ambition. She slummed it in a dorm while she juggled auditions, acting classes, and whatever work she could find. Her lackluster first year was a disappointment, but Holman refused to return home empty-handed.
6. Someone Saw Her Potential
Finally, her leap of faith paid off: Holman landed her first theater job. It was for the traveling performance of The Fool. Its writer, Channing Pollock, instantly recognized that she was a star in the making, and encouraged her to pursue theater. Thankfully she took his advice to heart. Otherwise, the world may not have “Moanin’ Low,” the Broadway song that launched her career into the stratosphere.
The Midwest girl finally had the career—as New York City’s best torch singer—to match her ambition. This theater success allowed Holman to make shocking career decisions.
7. She Rejected Hollywood
Holman looked at Hollywood’s promise of even greater fame and fortune… and rejected it! She didn’t only turn down these lucrative opportunities because she was a theater snob who looked down on movies. Or because she was a seductress whose gift was casting a spell over live audiences. The real reason was heartbreaking.
Deep down, Holman was insecure in her appearance. Admittedly, her looks were surprising and unconventional.
8. She Wasn’t Beautiful
Holman is proof that looks aren’t everything! She was a star, but not a conventionally beautiful one. Those who knew Holman remember her messy hair, near-sighted eyes, weak chin, complexion, and odd teeth. Holman’s face didn’t draw people in: her voice, figure, and charm did. Unfortunately, they didn’t just attract lovers, fame, and fortune. It drew in scandal and devastation.
9. She Scandalized Everyone
All those stereotypes about the 1920s? Holman lived that life for real. She was even wilder than an F. Scott Fitzgerald character. Holman partied all over the city in the most scandalous outfits. These included strapless dresses and men’s suits. One night, Holman and a lover rode a horse-drawn carriage down Fifth Avenue blowing kisses and yelling at strangers.
Holman’s music also reflected this rebelliousness. But like everything else, Holman took it too far—and paid the price.
10. Her Music Was Banned
Not all of Holman’s music is available today because some songs were so suggestive that radio stations refused to play them for decades. Due to the inevitable censorship, Holman didn’t bother recording many songs. But she continued to perform these racy love songs live to ravenous audiences. Much like Holman’s love songs, her life was unashamed and unconventional.
11. Her Love Life Was Controversial
The early 20th century wasn’t exactly the most accepting period—especially when your tastes are as scandalous as Holman’s. Despite the prejudices of the time, Holman didn’t hide that men and women attracted her. She also didn’t conceal her many public relationships with men and women, celebrities and nobodies.
Some of her most famous lovers include Montgomery Clift and Josephine Baker…but her most treasured relationship was with someone almost no one has heard of.
12. Her Most Important Relationship Started As An Affair
Heiress Louisa d’Andelot Carpenter fell in love—or lust—at first sight. Holman didn’t return this insta-love, but decided to give it a go since she found Carpenter attractive. Undoubtedly, the money and lifestyle didn’t hurt. To add to the scandal, Carpenter was already married to a man. They didn’t care and plowed forward.
13. She Was Different With Women
Haters were scandalized and judgmental, but they didn’t know the truth about the couple. Holman and Carpenter’s affair turned love was intimate and emotional. She was soft and sweet. This was a pattern with Holman’s relationships with women. But she did a complete 180˚ with men.
Shockingly, Holman was stone cold and ruthless with men—many found out the hard way. And some didn’t survive.
14. She Toyed With Men
Unsurprisingly, Holman’s taste in men was also scandalous. Physically, she preferred significantly younger pretty boys. Mentally, the femme fatale looked for male partners she found submissive, weak, and pliable. Basically, Holman desired pushovers she could control. It didn’t scare men: she had her pick of them. One day, Holman caught the eye of a young man. It was the beginning of the end for both of them.
15. She Had An Obsessive Suitor
Enter, Zachary Reynolds: heir and a lavish character straight out of an F. Scott Fitzgerald novel. He was all the excesses of the Roaring 20s distilled into a single person. After a performance, Reynolds became completely captivated by Holman. It was obsession at first sight. The 18-year-old was seven years younger than the star. But he had the drive and resources to become a creepy stalker in the name of love—the things he did were wild.
16. She Was Stalked
Reynolds coveted Holman and refused to take no for an answer. He attended almost all her performances and there were hundreds. Reynolds sent her flowers and love notes every single night. He stalked her around the globe. He begged her to dump Carpenter, who she was still seeing at the time. Holman found this obsession flattering but wasn’t interested in Reynolds; she even viewed him as a bumbling idiot. Her friends shared this view and treated him terribly.
Little did they know their treatment of him—along with Carpenter’s absence—softened her heart. What Holman did next shocked everyone.
17. She Married Her Stalker
Through willpower, stalking, and displays of wealth, Reynolds finally wore Holman down. After all, Holman remembered her impoverished upbringing all too well, and Reynolds had money to spare: his family was one of America’s richest, having made their fortune in tobacco. They married in 1931, much to the disapproval of everyone else in their lives. Disaster was incoming, but neither could tell.
18. Her Friends Had A Bad Feeling
Reynolds and Holman’s marriage shocked her friends. And it took a lot to scandalize her fellow scandal-makers! Many suspected this marriage was doomed. None of them was more heated about this than her now-ex-lover Carpenter. It wasn’t just jealousy either. She knew the marriage would end up in flames. She just couldn’t have known how bad it would get.
19. Her In-Laws Hated Her
Holman was a scandal maker: wherever she went, drama and wild friends followed. In comparison, the Reynolds family was traditional and conservative. The heir’s marriage was a nightmare for his wife and family. Like Holman’s friends, Reynolds’ family didn’t approve and shared a sinking feeling about it. And then trouble hit.
20. Her Marriage Was Awful
Imagine the bumpiest and roughest rollercoaster. That was Reynolds and Holman’s marriage. It turns out, he was in love with the idea of her. Once the excitement of courtship and marriage wore off, they had to face a horrible reality. They were utterly incompatible. Reynolds wanted Holman to quit working and become a trophy wife. She thought she wanted that too. But she actually craved the glitz and the glam.
The gold-digger realized the life she dreamed of—married to a millionaire—was actually boring. She didn’t want to stop working. He didn’t stop trying to convince her. And one day, he took it too far.
21. She Was Forced To Quit
Reynolds wanted Holman to quit acting and didn’t care if he had to terrify her to make it happen. One day, he pulled out a gun and pointed it at his head. Reynolds vowed to end his life if she didn’t obey him. Shocked and terrified, Holman agreed to stop working for a year and stay at his family’s lavish North Carolina estate.
This wouldn’t be the last time he brandished this instrument and terrified her. Holman felt trapped with an unstable and armed man who didn’t satisfy her. Her antagonistic in-laws made her life even worse.
22. Her Party Went Horribly Wrong
One year after their wedding, an unbelievable tragedy struck. The newlyweds threw a lavish party at the Reynolds estate. Initially, Holman was the life of the party. Mysteriously, her mood darkened as the luxurious celebration raged on. Holman drank. And drank. Then drank even more. She disappeared somewhere. The next time she appeared marked the beginning of a tragedy.
23. Her Husband Mysteriously Died
After midnight, Holman finally reappeared as the party winded down. Only two friends, Ab Walker and Blanche Yurka, remained in the home. Reynolds walked his very inebriated wife upstairs. Walker heard them arguing upstairs. Minutes later, their security guard heard a shot but dismissed it. He thought it was not a big deal. It turns out, it was.
Yurka woke up to a frantic Holman who screamed that Reynolds had shot himself. Just like that, a celebration turned into a suicide…or worse.
24. The Mystery Ruined Her Life
This wasn’t just a huge scandal in the star’s life. It was the biggest scandal of the year in the country. The incident itself was bad—but for Holman, the aftermath was so much worse. It forced Holman into the limelight, but not in the way she liked. The media and gossips tore Holman apart. From her clothes to career, they spared nothing. Reynolds’ untimely and mysterious demise became a national obsession.
Rumors and conspiracies of what actually happened exploded. Holman was at the center of all them. After one terrible night, her life was never the same.
25. Everyone Thought She Was Guilty
No one knew what actually happened, but it didn’t stop everyone from forming opinions. The Reynolds family insisted their heir took his own life. But the general public already made up their minds: Holman pulled the trigger and Walker helped. For the rest of her life, she couldn’t escape the scandal and suspicion. Even worse, the truth haunted even Holman.
26. She Had Amnesia
Losing your husband unexpectedly and prematurely is already tragic enough. Everyone believing you were responsible was even worse. But there was an even more sinister side to it all. Holman wasn’t sure of her innocence or guilt. She’d drank so much that night she couldn’t remember a single thing. This mystery haunted her.
For the rest of her life—until her own tragic end—Holman agonized over whether she was guilty. While Holman was never sure, everyone else believed she was. They wanted her to pay.
27. She Went On The Run
All of Holman’s past rebellions paled in comparison to this. After a grand jury indicted her and Walker, she went on the run. Law enforcement across four states couldn’t find the femme fatale turned fugitive. Eventually, Holman turned herself in. Turns out, she went into hiding at one of Carpenter’s estates. Things were not looking good for Holman—until an unexpected source saved her.
28. Her In-Laws Saved Her
Holman’s in-laws—wealthy, connected, and powerful—spared her from a court battle and possibly imprisonment. But it wasn’t out of love for their daughter-in-law. They all hated her. But, while Holman was no angel, neither was their son. Wanting to avoid more publicity, the family pressured the government to drop the case.
The prosecutors agreed—with the caveat that it could be reopened anytime. While Holman was free, that horrible night haunted her forever. On top of that, she and the Reynolds family were still set on a collision course for another conflict in court.
29. They Didn’t Believe Her
The aftermath was one thing—but Holman was in for an even more shocking surprise. She found out that was pregnant, and even more drama ensued. The Reynolds were suspicious: they believed her son wasn’t Zachary’s child. They even speculated it was Walker’s! They never liked Holman and now had even more reason to dispute the baby’s paternity.
According to Zachary’s will, his fortune would go only to his child. Life changing money was up for grabs and everyone wanted a slice…perhaps none more than a certain gold-digger.
30. She Paid Price For Wealth
The battle over the Reynolds estate took years to settle, but Holman emerged victorious. She received $750,000 while their son Christopher got $6,250,000. Holman finally achieved her dreams of being independently rich. She never had to work a day in her life again. But when the young girl set out to marry rich, she didn’t imagine the cost was a man’s life, endless drama, and a ruined reputation.
31. Her Peace Didn’t Last
In the rubble of Holman’s post-scandal life, she found peace. Louisa and Holman got back together openly. They—along with their children—lived together for years. Like all good things in Holman’s life, this serenity didn’t last. The couple broke up again, though remained friends for the rest of their lives. Holman’s career, on the other hand, didn’t survive the scandal.
32. Her Scandals Caught Up To Her Career
Thanks to Holman’s notorious personal life, her once glittering career dulled. Even when Holman was lucky enough to find work, it came with a devastating caveat. She knew it was only because producers hoped her notoriety attracted audiences. For the most part, it didn’t work and her projects flopped. When people came to her shows, she faced heckling.
Holman couldn’t escape her past—but found what she hoped could be a fairytale ending to her nightmare.
33. She Had A Whirlwind Romance
Holman couldn’t believe her luck: Phillips Holmes appeared to be Prince Charming, a fantasy come to life. He was exactly her type: young, good-looking, and pliable. Just a month after meeting, Holmes moved in. The lovers were moving fast—too fast. They learned the hard way that Holmes wasn’t Prince Charming, and Holman wasn’t Cinderella.
34. She Fell Out Of Love
Once the high of the whirlwind romance wore off, Holman realized the dark truth. Holmes wasn’t really a catch. Her Prince Charming was actually a mess! He was too dependent, too much of a drinker, and too messy. On top of that, Holmes insisted she marry him and quit working. Doesn’t that sound familiar? As history began repeating itself, Holman was doomed.
35. She Hid A Big Secret
Soon after getting together with Holmes, Holman was horrified after discovering she was pregnant with his child. She was certain she didn’t want to marry Holmes. But having a child out of wedlock guaranteed yet another scandal. So she made a heartbreaking decision. She had a secret abortion. While Holmes had no idea, Holman couldn’t forget.
She blamed him: had he been less of a mess, she would’ve kept the baby. This, along with all the other issues, destroyed their relationship. But Holmes remained clueless and had no idea what she would do next.
36. She Abruptly Dumped Him
When Holmes returned from a trip, he expected hugs and happiness. What he got instead was heartbreak. Holman kicked him out the very same day. Understandably, this devastated her younger lover. The stone-cold woman didn’t even explain why she abruptly ended the relationship. The shocking betrayals didn’t end there for poor Holmes.
37. She Committed The Ultimate Betrayal
Holman didn’t just dump Holmes, she dealt him a brutal betrayal. Turns out, she was cheating on him! It gets even worse: she betrayed him with his younger brother Ralph Holmes! Holmes just couldn’t catch a break, with a surprise breakup and a double betrayal. Tragically, both brothers had worse fates in store.
38. She Lost Her Ex
When WWII broke out, both brothers joined the Air Force. One day, Phillips Holmes called his ex-lover to say goodbye. He was about to leave to fight in Europe. Her maid rejected his call. Shortly after, his plane crashed. There were no survivors. She never got to say goodbye. Lucky for Holman, she still had one more Holmes brother to go through.
39. She Had A Secret Wedding
In a double betrayal to Phillips, Ralph Holmes and Holman secretly married. He was even younger and more handsome than the older Ralph. Perhaps Holman thought she avoided history repeating by dumping Phillips. Turns out, this marriage was still cursed—just in a different way. Once more, WWII tore the couple apart. And what they did while apart was controversial, even by today’s standards.
40. She Had An Open Marriage
While Ralph was off serving in Europe, Holman picked up stranger after stranger. She enjoyed countless lovers. This time, it wasn’t infidelity—it was somehow even more scandalous. Turns out, Ralph and Holman secretly had an open marriage. While they were apart, both could take whoever they wanted as lovers, no strings attached. They just had to be honest with each other.
But that didn’t mean everything was serene: One day, Holman received a letter that left her shocked to her core.
41. He Betrayed Her
Their marriage was open, but Ralph still managed to betray her. One day, Holman received a letter from a Lili, one of Ralph’s French lovers. The letter insisted they were in love. Lili said she would convince Ralph to stay in Paris. He didn’t, but in retaliation, Holman embarked on a year-long affair with a woman she didn’t tell him about.
The arrangement they thought would save their marriage blew up in their faces. Their relationship worsened even more after Ralph returned.
42. She Lost Her Husband
In 1945, Ralph came back a WWII veteran and a changed man—and not in a positive way. Holman could barely recognize her once shiny boy toy. Now, he had a disturbing dark side. He drank too much, devoured pills, gained weight, became a sloth, and neglected her. Stone cold as usual, Holman had no sympathy for her men. She kicked him out and unknowingly sent him down a dark path.
43. She Lost Her Husband For Good
Just six weeks after their breakup, Ralph’s body was discovered in his apartment. He’d been dead for nearly a whole week before anyone noticed. An overdose had been the cause. Once again, mystery shrouded the demise of Holman’s husband. This time, no one knew if it was intentional. He was the third man in her life whose life ended prematurely after meeting her. Tragically, he wouldn’t be the last.
44. She Lost Her Guiding Light
Libby’s life was chaotic, but she always had her father, despite their differences. Alfred remained the figure of stability throughout scandal after scandal. Sadly, he passed from unexpected heart problems in 1947—just three weeks after she adopted two sons. This destroyed Holman…but even more loss was in store for her.
45. She Lost Her Sister
Were the Holman sisters cursed? The pair shared the same mental health struggles and personal demons. One day, Marion intentionally took too many pills and didn’t survive. Tragically, the younger sister was doomed to follow in her footsteps, particularly after losing so much. There was only so much heartbreak one human heart could take.
46. She Lost The Most Important Person
In 1950, Holman gave her beloved son Christopher permission to climb Mount Whitney with his friend. It was a dire mistake. They were almost at the top when they decided to take a different, nearly impossible trail. The 17-year-old never made it back down. Of all the losses Holman suffered, this was by far the worst. She became a shell of her former self. Even worse, the devastated mother blamed herself.
Holman tried to turn this grief into something good—and revealed a secret side.
47. She Was Ahead of Her Time
After her son’s dark end, Holman was a rebel with a cause. This time, her rebellions were positive. She was an early and ardent supporter of the Civil Rights Movement. The Jewish woman related to the struggles of African Americans. She started a charity in her son’s name. This foundation donated money to Martin Luther King, who was extremely appreciative.
Holman and his wife Coretta even became friends. And they weren’t the only famous friends she made.
48. She Had A Famous Lover
In her late 40s, Holman and heartthrob Montgomery Clift became a couple. They were an unlikely pair: he was 17 years younger and at the height of his fame. This relationship baffled her friends. No one thought it would last or end well. Shockingly, the pair lasted almost a decade—though not without problems. Demons haunted both of them, even Clift.
Behind his legendary good looks, the actor drank too much, took too many pills, and struggled with his sexuality. Sadly, Holman’s issues were even worse.
49. She Had Health Problems
Throughout the years, Holman’s emotional pain was excruciating—and worsening. In her later years, her physical health became just as bad, thanks to ulcers. There were times when the pain was so agonizing Holman found herself screaming in the car. They cranked the radio volume all the way up so nearby drivers wouldn’t freak out.
She even had a harrowing surgery to remove 87.5% of her stomach. Yet the worst was yet to come.
50. She Struggled With Demons
As Holman got older, the worse her mental and physical health became. She fell into a very deep and dark depression. The former star was once the Master of Broadway. Now, she called herself the “Master of Melancholy”. Her demons led her down the path to yet another doomed relationship. Was Holman cursed? This time, it was with someone completely unexpected.
51. Her Final Husband Shocked Everyone
Holman was scared she would never find love again and jumped into a marriage with artist Louis Schanker. This choice, as many of her choices did, baffled friends. Shockingly, Schanker was older than Holman. He also wasn’t handsome, educated, or cultured. Basically, he was the complete opposite of her type. But that wasn’t the only problem.
Schanker was even already in another relationship. Once again, friends couldn’t help but fear this would end in heartbreak again. Unfortunately, they were right.
52. He Mistreated Her
This time, Holman was secretive about her marriage, even with friends. But it was clear something was wrong. Her depression worsened. Her friends felt alienated. They witnessed some of his poor treatment of her, including openly making suggestive comments to other women. But they had no idea how awful it really was.
Only their household staff truly knew. Her butler even said “I don’t know whether she killed Smith Reynolds or not, but the husband she ought to kill is Louis Schanker”.
53. He Was Possessive
Marrying Holman turned Schanker into a wealthy man. After this windfall, he became unambitious and a mess. He drank too much and clashed with Holman’s children. His treatment of her was even worse. If her friends felt unwelcome, they were right. Turns out, he banned them from coming over out of possessiveness and jealousy.
Isolated and miserable, Holman drank to cope. Somehow, her life got even worse.
54. She Lost Her Friends
How much loss can a single person stand? Holman already lost: her son, father, sister, ex-lover, and three husbands. The heartless universe threw even more tragedy her way. In just five years, she lost countless friends and lovers. These included Lucius Beebe, Clifton Webb, Tallulah Bankhead, Josh White, and Montgomery Clift. She just couldn’t catch a break.
55. She Lost Her Idol
Holman lost almost everyone and was hanging on by a thread. At least she had the Civil Rights Movement, particularly Martin Luther King. She even once told him “There are no words that I have to express to you the gratefulness in my heart that you exist”. Months later, King was also taken from the world too soon. Holman didn’t just feel unlucky, she felt cursed.
56. She Felt Cursed
As the tragedies piled up, Holman believed she was responsible for everything. What are the chances that so many people connected to her met such untimely ends? Some even believed she was a witch. Homan saw herself as a vessel that transferred loss onto loved ones. Holman felt cursed with life: she survived and had to feel this pain. One day, she had enough.
57. She Ended It
All stars eventually burn out and Holman was no exception. On June 18, 1971, they made a shocking and tragic discovery at her Connecticut mansion: her lifeless body in a Rolls Royce. The aging and troubled icon decided to go out on her own terms. She was survived by her husband and two children. It was a tragic end to a legendary life.