While riding a crest of Broadway stardom – and in a serious romance with a woman – Libby is pursued by Zachary Smith Reynolds, the reckless, emotional teenage heir to the Camel tobacco fortune. Just months after their marriage, at the close of a drunken party, Reynolds is dead of a gunshot wound to the head. Was Libby responsible? Also: Tallulah Bankhead is brought to Hollywood to compete with bisexual icon Marlene Dietrich, while Libby, no stranger to blackface, wants to star in a film about Josephine Baker.

(00:00) Libby’s Heiress Girlfriend

(13:15) Libby’s Tobacco-Heir Boyfriend

(19:25) Tallulah Bankhead & the Gary Cooper Threesome

(37:16) Libby Tries to Play Josephine Baker in Movie

(43:56) A Yankee Jewess on the Plantation

(54:36) Who Shot Zachary Smith Reynolds?

Libby Holman, a Jewish girl from Cincinnati, arrives in Manhattan in 1925 and begins to make a name for herself as a torch singer, trading on her racially-ambiguous skin tone and deep voice at a time when white hipsters think the height of cool can be found in Harlem. Libby and friends like Tallulah Bankhead sojourned uptown not just to listen to Black music, but also to explore their bisexuality. Through mutual co-star Clifton Webb, Libby meets Jeanne Eagels – one of the greatest actresses of her generation, and a high-profile casualty of Roaring 20s debauchery.

(00:00) Torch Singer, Accused Murderess, Bisexual

(09:05) A Confederate Jew

(17:53) Sex Appeal to Burn

(25:59) “Coon Shouting” and Libby’s Racial Ambiguity

(41:32) Blackface on Broadway with “Moanin’ Low”

(49:10) Sex Tourism in Harlem

(58:28) Jeanne Eagels

Listen to a trailer for The Bisexuals, the new season of You Must Remember This, coming September 15.

A sultry, racially-ambiguous singer who became a sensation on Broadway in the late 1920s and 30s, Libby Holman popularized a number of jazz and blues standards of the Great American Songbook. At the height of her fame, Holman shocked her mostly queer coterie by marrying the heir to the Camel cigarettes fortune. Within months, Libby’s husband was dead, and Libby was accused of his murder. The ensuing scandal marked the star as a “black widow,” and in the years to come, a number of friends and lovers who drifted into Libby’s web wound up dead. The most famous of these was Montgomery Clift, who like Libby was bisexual, struggled with substance abuse, and felt misunderstood within a pop culture that increasingly demonized anyone who didn’t fit neatly into the post-WWII American ideal.

Over 8 episodes – with a cast of characters including Elizabeth Taylor, Josephine Baker, Tallulah Bankhead, Billie Holiday, Jane and Paul Bowles, Nicholas Ray and more – The Bisexuals will begin by describing Libby’s rise to stardom, and her sexually-fluid social life, in the New York theater scene of the 1920s. From there we’ll explore the murder scandal that transitioned her from fame to infamy in the 1930s. Then, we will skip to the 1940s and 50s, and a very different climate than the free-wheeling 1920s when Libby Holman thrived. The cultural pendulum had swung back the other way, and there was no possibility for a movie star like Monty Clift to be openly queer. By the time the social and sexual revolutions of the 60s began to be felt, both Libby and Monty were too deeply scarred by trauma, stigma and addiction to benefit.

If you're a fan of You Must Remember This, we think you'll also enjoy Talking Pictures, a podcast from TCM and HBO Max. On this episode, Oscar-nominated actress Rosie Perez sits down with host Ben Mankiewicz to discuss the films that shaped her career—Do the Right Thing and Fearless—as well as early favorites like Saturday Night Fever and Double Indemnity. She reflects on building a career in an industry that didn’t readily accept her for who she is, and speaks candidly about being raised in a strict Catholic home for girls. In the Super 8 segment, she tells Ben about an amazing boxing story she’d love to see on the big screen.Listen to Talking Pictures wherever you get your podcasts, or watch on HBO Max

If you like You Must Remember This, you might also enjoy Cautionary Tales with Tim Harford, a

podcast about stories of historic human error, catastrophes, and heists, and the lessons we can

learn from such mishaps. In this episode of Cautionary Tales, Tim examines what happens when the bright lights of Hollywood collide with the far less glamorous world of tax evasion.

When Ernest Borgnine was cast as the lead in the 1955 romantic drama, Marty, he thought it

was his big break. But he soon discovered Marty was not exactly a dream gig. Listen to

Cautionary Tales every Friday wherever you get your podcasts.

If you’ve finished all episodes of The Old Man is Still Alive, I’ve got another treat for you from Jake Brennan at Hollywoodland. Have a listen to this episode of Hollywoodland about John Waters, from his beginnings in X-rated art films to cult classics like Hairspray and Crybaby, as he created and cultivated his own peculiar niche in film while nurturing a legendary troupe of players who became a family of outcasts.

In part two of our season finale, we explore the final decade of John Huston’s life and career. As he was slowly dying of emphysema and undergoing massive turmoil in his personal life, Huston continued to work almost compulsively on both passion projects (The Man Who Would Be King, Wise Blood, Under the Volcano) and paycheck gigs (Annie). His career ended, fittingly, with two collaborations with the next generation of Hustons, Prizzi’s Honor and The Dead.

(00:00) The Man Who Would Be King

(10:20) Marital Strife and Relocating to Puerto Vallarta

(16:37) Wise Blood

(20:49) Annie

(29:25) Under the Volcano

(34:49) Prizzi’s Honor

(42:42) The Dead and The Old Man is No Longer Still Alive

This series began with the story of a director who wrote his autobiography to secure his place in history after his career had gone down the drain. It ends with the story of a man who wrote his autobiography as a “dead man walking”...and then continued to make movies for another half a decade, until the literal last breath left his body. Hollywood’s original “nepo baby” director, John Huston was never a conventional studio system stalwart, and in some respects he was able to go with the flow of changing times a lot better than some of his contemporaries. In part one of our two-part season finale we’ll talk about his flight from Hollywood to Ireland, literally playing God, Huston’s long fallow period in the late 60s, Anjelica Huston’s misbegotten film debut, Huston’s reinvention in the New Hollywood era and the health crisis that almost ended it all.

(00:00) John Huston…In the Beginning

(09:22) Huston in Exile

(15:40) Playing God and Facing Mortality

(24:01) Casting Anjelica and Working with Orson Welles

(34:11) Fat City

(41:43) Noah Cross and Chinatown