- Jim Parsons - Henry Wilson
- Patti LuPone - Avis Amberg
- Rob Reiner - Ace Amberg
- Maude Apatow - Henrietta
- Mira Sorvino - Jeanne Crandall
- Michelle Krusiec - Anna May Wong
- Paget Brewster - Tallulah Bankhead
- Queen Latifah - Hattie McDaniel
- Alison Wright - Ms. Roswell
- David Bluvband - Lew
- Brea Bee - Woman
- Courtlyn Cannan - Woman (20s)
- Kelly Chavers - Waitress
- Bob Glouberman - Dr. Algren
- Adam Bucci - 2nd AC (Camille)
- Anthony Fanelli - Radio Correspondent
- Billy Boyd - Noel Coward
- Harriet Sansom Harris - Eleanor Roosevelt
- Daniel London - George Cukor
- DeJean Brown - Sharecropper Dad
- Dalton Baker - Randy
- Chris Dotson - Cy Freeman
- Carrie Gibson - Dorothy Arzner
- Darren Richardson - Cole Porter
- Timothy Dvorak - Irving Thalberg
- Fred Grandy - C. Aubrey Smith
- Joe Marinelli - Sidney Franklin
- Camille Natta - Luise Rainer
- Carey Scott - Leo McCarey
- Herbert Russell - Len Schlossen
- Samuel Caleb Walker - Rory Calhoun
- Jacob Kyle Young - Tab Hunter
- Nicola Bertram - Gertie
- Aidan Bristow - George Hurrell
- Brian Chenoweth - Lon Silver
- Frank Crim - Mickey Cohen
- Dan Dore - Gregory Hall
- Monica Lee Gradischek - Lucille Reimann
- Christine Kilmer - Ethel
- Kerry Knuppe - Sally
- Brian Konowal - Carl Williams
- Christian Martin - Dean Wharton
- Colette McDermott - Josephine
- Elizabeth Schmidt - Phyllis Gates
- Daniel Hagen - Joseph Breen
- Jake Regal - Erwin Kaye
- Mitch Eakins - Robert Montgomery
- Rachel Emerson - Rosalind Russell
- William Frederick Knight - Harry Golden
- Nick Milone - Football Player 2
- Katie McGuinness - Vivien Leigh
- Derek Chadwick - Quarterback (uncredited)
- Jessy Greer - Sex Worker 2
- Chad Doreck - John
- Barry Ratcliffe - Auctioneer
- Jim McCaffree - Academy Official
- Pierce Nasser - Football Player 11
- Tanase Popa
- Ned Martel
- Sara Stelwagen
- Todd Nenninger
- Todd Kubrak
- Julie Herrin
- Nathan Barr
Harriet Sansom Harris interpreta a Eleanor Roosevelt en la serie.
Billy Boyd interpreta a Noel Coward en la serie.
Darren Criss interpreta a Raymond Ainsley en la serie.
Rob Reiner interpreta a Ace Amberg en la serie.
David Corenswet hace el papel de Jack Castello.
Jim Parsons interpreta a Henry Wilson en la serie.
Laura Harrier interpreta a Camille Washington en la serie.
Joe Mantello interpreta a Dick Samuels en la serie.
Dylan McDermott hace el papel de Ernie West.
Jake Picking hace el papel de Rock Hudson.
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