Monty’s cataclysmic car accident throws a wrench in his stardom, his mental and physical health, and his relationship with Libby, who begins to see Monty’s other beloved female friend, Elizabeth Taylor, as an enemy. Monty tries to get his career on track by making a number of interesting films, including Lonelyhearts and Wild River. But by the time he’s shooting The Misfits in 1960, his relationship with Libby is so strained that she marries someone else – a man who doesn’t want his new wife to have anything to do with Clift, or anyone else who presents as queer.

(00:00) Raintree County and Clift’s Crash

(07:40) Libby vs. Liz Taylor

(13:02) Written on the Wind

(20:49) Jane Bowles’s amour fou

(31:17) The Young Lions and Monty’s Broken Heart

(38:30) Lonelyhearts

(48:48) Monty’s Last Chance at Straight Romance

(55:34) The Misfits 

(01:01:44) Libby Gets Married

Monty’s arc as a tragic romantic figure continues with I Confess and Terminal Station – even as his relationship with Libby becomes all consuming, in the decadent party scene at her secluded estate. Meanwhile, Libby brings her act singing black folk music to Broadway, but her dreams of renewed stardom turn out to be one thing money can’t buy.

(00:00) Montgomery Clift’s Juggling Act

(07:54) Partner Swapping with Paul Bowles

(11:13) An American Tragedy vs. A Place in the Sun

(16:09) I Confess

(28:43) “Love relationships are ludicrous”

(36:20) “Everything seemed erotic”

(44:03) Blues, Ballads and Sin-Songs

(50:49) Oedipal Overtones

With Red River, Montgomery Clift becomes a new kind of movie star, projecting a new kind of sexuality – while still figuring out how he wants to express his own sexuality. Meanwhile, Libby becomes entangled with bisexual couple Jane and Paul Bowles, whose globetrotting becomes an inspiration to Libby’s teenage son, ending in tragedy. Plus: did Libby forbid Monty from starring in Sunset Boulevard because the story of a young man and a haunted older woman hit too close to home?

(00:00) Affair with Nick Ray and Influence on Key Largo

(09:42) Digging Deeper into Black Folk Music

(14:32) Jane and Paul Bowles

(25:00) The Tragedy of Libby’s Son, Topper

(32:15) Montgomery Clift’s Bisexuality

(40:34) Red River as Queer Melodrama

(48:53) The Heiress and Monty Reconnects with Libby

(57:48) Did Libby Bar Monty From Starring in Sunset Boulevard?

Montgomery Clift enters the chat as a teenage acting prodigy who immediately attracts 34 year-old Libby’s attention. Through her sometime-lover Nicholas Ray, Libby starts exploring Black folk music, launching a new singing career in collaboration with guitarist Josh White (“One Meatball”). Plus Libby’s old friend Clifton Webb becomes a late-in-life, closeted movie star, and Tallulah – effectively banished from Hollywood a decade earlier due to her refusal to be discreet about her sexuality – triumphantly returns to the screen thanks to Alfred Hitchcock.

(00:00) Libby and Monty “Under the Sheets”

(03:51) Appreciation or Cultural Appropriation?

(06:23) Nicholas Ray, Leadbelly, Josh White

(13:24) No White Person Has Ever Sung Them in Public

(22:02) Everybody is in Love With Monty

(28:44) Tallulah Bankhead in Movie Jail

(36:13) Lifeboat

(40:20) Clifton Webb’s Queer Success Story

(45:46) Libby Lashes Out at Older Women

(51:08) The Black Widow and Josh White

(58:45) Libby’s Only Movie

While the racist, antisemitic Southern authorities try to indict a pregnant Libby for the murder of her husband, the national media effectively puts her on trial. When Libby gives birth to a new Reynolds heir, the circus only grows bigger. Meanwhile, Hollywood gets to work dramatizing the case with the aid of stars such as Claudette Colbert, Jean Harlow and Libby’s friend Franchot Tone.

(00:00) A Pre-Code Anti-Heroine

(04:53) A “Peculiar Opinion” of Jews

(11:09) Libby Testifies

(17:23) Indicted by Jury, Convicted by Media

(29:09) Who Actually Killed Smith Reynolds?

(34:19) Pre-Code Movies Inspired by Libby’s Story

(42:50) A Career Tainted by Scandal

(52:38) Jean Harlow as Libby Holman

(01:02:02) An American Tragedy

(01:09:11) Lupe Velez, Libby’s Nemesis

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.