1. This photo was taken on New Year's Eve at the Royal York Hotel in Toronto — revellers ringing in 1942.

I stumbled across it last night. And it turns out there's a story behind this photo: a wild, tragic tale filled with scandal, war, Broadway stars & betrayal.

2. The woman on the right of that photo is Libby Holman. She was one of Broadway's brightest stars in the 1920s and '30s — and one of its most notorious party animals.

She took lovers, made enemies & knew how to leave an impression.

3. She was a singer, actor & fashion icon. "A photographer's pride and a photographer's heaven." Some give her credit for inventing the strapless dress — at the very least, she helped popularize it as her signature look. And she was fodder for the gossip pages, too.

4. Libby Holman partied her away through glitzy galas, opera openings, Harlem jazz clubs & fancy Manhattan super clubs. Her own parties were so over the top that hotels started to refuse her bookings.

5. Take, for instance, the bacchanalian birthday bash she threw for her *six year-old son*. It went all night. Billie Holiday, Benny Goodman & Gene Krupa all performed.

"That was one hell of a party," Holiday later remembered, "the way a party's supposed to be."

6. Not everyone loved Holman. She was as sharp-tongued as she was quick-witted. When she performed in a big Cole Porter musical, her co-star Lupe Velez hated her so much that Velez started pissing in the wings of the stage, hoping Holman would slip and fall in the puddle.

7. But men *adored* her. One Broadway producer called her an "irresistible enchantress [who] could exert a strange fascination." They say men followed her around "like puppies." She had affairs with many of them — some, like Montgomery Clift, scandalously young.

8. But Holman was just as interested in women as men — if not more so.

She had a long romance with DuPont heiress Louisa Carpenter, a tempestuous affair with the famous actor Tallulah Bankhead, and countless others. There were even rumours she was sleeping with Josephine Baker.

9. Holman's first husband was the heir to a big tobacco company (that made Camels, Newports & Pall Malls). He, like so many others, was hopelessly devoted to her. Whenever they were forced to spent time apart for work, he plunged into depression, threatening suicide.

10. The marriage didn't last. He died under suspicious circumstances: shot in the head after he & Holman had a big fight at a party.

Some said he'd died of suicide. Others, including the coroner, thought he'd been murdered.

11. It was a just few years later that Libby Holman fell in love with the man on the far left of this photo.

His name was Phillips Holmes. He was a fellow actor from a family filled with big Broadway stars, including his mom — a theatre actor from Canada.

12. Holmes, too, was obsessed with Holman. He desperately wanted to get married. But she knew it would never work: he was WAY too traditional; he wanted to be the breadwinner while she gave up her career to stay home.

13. When she got pregnant, she hid it from him — had an abortion and never told him. Their relationship didn't last long after that. They fought more and more. Finally, in the spring of 1938, she kicked him out of the house.

14. Phillips was soon found by friends living at the Ritz Hotel in London: drunk, unshaven, sick, his bed soaked in piss & vomit, a whole wall of his hotel room plastered with photos of Holman, desperate for any news of her.

15. Little did he know the awful truth.

Libby Holman had been having an affair with Phillips' own brother: Ralph Holmes, the man on the far right of this photo.

16. Libby & Ralph got married a year after she & Phillips broke up.

It wasn't an easy marriage. He was 11 years younger (23 to her 34), homophobic (and thus didn't get along with many of her friends) and, y'know, her ex-lover's brother.

But she really did love him deeply.

17. It was the outbreak of WWII that finally drove them apart.

Ralph was determined to do his part in the fight against the Nazis—even though the U.S. wasn't in the war yet. And since he was half Canadian, he was planning to head north & enlist with the Royal Canadian Air Force.

18. Libby tried to talk him out of it, but he wouldn't listen. He would spend the next three years training pilots on a base in Hamilton. He and Holman barely ever got to see each other.

19. This photo of New Year's is one of the fleeting moments they did get to spent together during those hard years apart. Phillips was even there, doing his best to forgive them.

But it was only a brief flash of happiness. Both brothers were doomed… and the clock was ticking.

20. It was Phillips who would die first. He joined the Royal Canadian Air Force, too — he'd enlisted that very week, on Boxing Day. When that photo was taken, he was about to head off to Regina for training.

21. When he passed his flight test, knowing he was about to be sent off to war, he called Libby one last time. She didn't answer the phone. He left a message with her maid, saying goodbye.

22. Days later, he took his final flight from a base in Northern Ontario. Shortly after taking off, his plane smashed into a second aircraft in midair. There were no survivors.

Holman came back to Toronto, this time with his sister to collect the body.

23. Ralph would get to live a little longer — long enough to see the end of the war, but only barely. And before he died, he and Libby would be torn even further apart.

24. The RCAF sent him to England. He and would eventually transfer to the U.S. Air Force, spending the last two years of the war flying bombing runs over Germany. He & Holman didn't get to see each other at all during that time.

25. They had an open marriage, promising to tell each other about all the other men & women they slept with. During the war, Holman began having more affairs than ever before, random hook-ups with strangers, waiters, maître d's, truck drivers.. .

26. "[Her] carnality was unbridled and obstinate," according to her biographer. "Men … were little more than rash adventures."

And Holman told Ralph all about it in her letters, while he wrote back about what it was like to sleep with French women, Italians, Swedes…

27. The big blow came when Holman got a letter from a French woman who Ralph had never mentioned, claiming he'd fallen in love with her. It was a deep betrayal, a shattering of the trust they'd built. The marriage deteriorated from there.

28. When the war ended & Ralph finally came home, Libby was still elated to see him — she threw a bunch of massive all-night bashes to celebrate. But he hated them: exhausted by the horrors of war, he just wanted some quiet time to get to know each other again.

29. He started drinking more. Put on weight. Got hooked on sleeping pills, wanting to spend as little time as possible awake to escape his memories of the war. The physical attraction Holman had once felt so strongly for him faded away. They barely slept together at all anymore.

30. They separated the very same month the war came to an end.

And he died just three months after that, his body found in his Manhattan apartment, killed by an overdose of barbiturates. He was 29.

To this day, no one's sure whether it was an accident or suicide.

31. As for Libby Holman, she would live another 20 years—and make good use of that time.

While Ralph was away at war, she'd gotten interested in blues music & became an early white ally in the fight for Civil Rights, demanding night clubs allow her to play with Black musicians.

32. She would eventually become good friends with Martin Luther King Jr. & his wife, Coretta Scott King. Holman created a charitable foundation, supporting the cause financially — as well as environmentalism, human rights & the peace movement.

33. When King was assassinated, it hit her hard. So did the killings of the Kennedys & the mass deaths of the Vietnam War. Her son died. And so did her dear friend Montgomery Clift.

It all took a terrible toll on her mental health.

34. On a June day in 1971, Libby Holman was found in the front seat of her Rolls Royce, having poisoned herself with carbon monoxide.

A truly remarkable life had come to a deeply tragic end.

35. But there in the archives of the Toronto Star, you'll find a touching reminder of happier times...

There's a second photo from that New Year's Eve at the Royal York Hotel: Libby Holman beaming up at her half-Canadian husband before it all went wrong.

Thanks so much for reading! If you'd like more love stories from the history of the city, the very first copies of The Toronto Book of Love have probably just arrived at your favourite local bookstore. #bookofloveTO