With Red River and A Place in the Sun, 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