A Yankee Jewess in the Deep South (The Bisexuals, Part 2)

Summary of A Yankee Jewess in the Deep South (The Bisexuals, Part 2)

by Karina Longworth

1h 6m•September 22, 2026
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Overview of A Yankee Jewess in the Deep South (The Bisexuals, Part 2)

This episode of You Must Remember This continues the story of singer Libby Holman, focusing on her bisexual and queer social world in late-1920s/early-1930s New York, her romance with the wealthy Smith Reynolds, and the complicated racial, sexual, and class dynamics that shaped their marriage. Karina Longworth traces how Libby moved between Harlem nightlife, celebrity circles, and Southern high society, culminating in the night Smith Reynolds was found dead at the Reynolds family estate in North Carolina.

Main Topics Covered

Libby Holman’s queer social circle

  • Libby’s closest friends and companions were often openly queer or sexually fluid figures.
  • Key names discussed include:
    • Clifton Webb
    • Tallulah Bankhead
    • Beatrice “B.” Lilly
    • Louisa Dandolo Carpenter (a DuPont heiress and one of Libby’s most enduring romantic partners)

Libby and Louisa Carpenter

  • The episode emphasizes that Libby’s relationship with Louisa was public and long-lasting.
  • Louisa is described as unusually open about her sexuality for the era.
  • Their relationship shaped Libby’s presentation, including her adoption of men’s suits and hats and the acceptance of a Rolls-Royce from Louisa.

Smith Reynolds enters the picture

  • Zachary Smith Reynolds, heir to the Reynolds tobacco fortune, becomes obsessed with Libby.
  • Their courtship is marked by:
    • his jealousy
    • threats of self-harm
    • attempts to control her career
    • his insistence that she quit show business if they married
  • Libby initially did not take him seriously, but he persisted until she eventually agreed to marry him.

Tallulah Bankhead and Hollywood

  • Long section on Tallulah Bankhead’s early Hollywood career.
  • The episode contrasts her stage charisma with the way Paramount tried unsuccessfully to market her as a “Dietrich-style” sex symbol.
  • Films discussed include:
    • Tarnished Lady
    • My Sin
    • The Cheat
    • The Devil and the Deep
  • Longworth argues that Bankhead had a distinct screen persona, even if the studio system tried to force her into a pre-existing mold.

A possible Tallulah/Libby/Gary Cooper threesome?

  • The episode examines a rumor that Libby once told Smith Reynolds she had had a threesome with Tallulah Bankhead and Gary Cooper.
  • Longworth treats this skeptically, suggesting it may have been an invention or exaggeration designed to:
    • assert Libby’s independence
    • unsettle Smith
    • remind him that he did not control her

Libby in the South

  • After marriage, Libby moves to Reynolda, Smith Reynolds’s North Carolina estate.
  • There, her celebrity, Jewish identity, Yankee background, and casual racial egalitarianism made her an outsider in a segregated tobacco-baron society.
  • The episode highlights how local elites saw her profession as morally suspect and how her friendships with Black people and queer visitors intensified suspicion.

Race, Black music, and cultural appropriation

  • Longworth addresses the uncomfortable reality that Libby’s career depended heavily on Black musical forms and aesthetics.
  • She notes that at the time, the white press praised this without much criticism, even as modern listeners would identify it as appropriation.
  • At the same time, the episode argues Libby genuinely admired Black culture and later devoted time and money to supporting Black artists and causes.

The Story’s Climax: Smith Reynolds’s Death

The party at Reynolda

  • Libby invites friends to the estate for a holiday weekend.
  • Smith becomes increasingly uneasy about the “queer” crowd surrounding his wife.
  • On the night before the fatal shooting:
    • a small domestic conflict escalates
    • Smith and his employee/friend Abner “Ab” Walker end up at a downtown hotel
  • At the party itself, Smith is humiliated and emotionally unstable.

The shooting

  • In the early morning hours, Libby is found in a bloodstained negligee and Smith is rushed to the hospital.
  • Smith dies from a gunshot wound to the head.
  • The episode emphasizes that the exact facts are murky:
    • was it suicide?
    • murder?
    • an accidental shooting?
  • What is certain is that the event immediately became a national sensation.

Media frenzy

  • Journalists descend on North Carolina.
  • The story is framed as a huge scandal involving:
    • a glamorous Broadway star
    • a wealthy heir
    • sex, booze, homosexuality, and violence
  • The episode closes by setting up the next installment, in which Libby Holman will be “tried” in the press.

Key Takeaways

  • Libby Holman lived at the intersection of queerness, celebrity, race, and class, and the episode shows how those forces shaped her public image.
  • Smith Reynolds’s love for Libby was deeply possessive and destabilizing, with his jealousy escalating into emotional abuse and tragedy.
  • The South treated Libby’s modernity as a threat: she was Jewish, from the North, sexually nonconforming, friendly with Black people, and a professional performer.
  • Tallulah Bankhead serves as both a parallel figure and a lens through which the episode explores bisexuality, performance, and the limitations of early Hollywood.
  • The episode suggests that Libby’s life cannot be reduced to scandal; even in the middle of the Reynolds tragedy, she remained a complicated, self-directed artist with her own desires and loyalties.

Episode Setup for Part 3

  • The episode ends on a cliffhanger:
    • Smith Reynolds is dead
    • the national press is mobilizing
    • Libby Holman is about to be put on trial by public opinion
  • Next episode: the aftermath of the death and the media’s obsession with proving what really happened.