- Cindy Ralston - Mrs. Milford
- Jeanmarie Collins - Mrs. Riggs
- Lucas Dixon - Lt. Hammett
- Maya Kazan - Livye Hart
- Scott Rosenfeld - Peyton Mathis
- Tom Bair - Mr. Weaver
- Philip Hoffman - Mr. Little
- Olli Haaskivi - Vogel
- Jamie Anne Allman - Tootsie Sayre
- Charity Jordan - Katie
- Talia Balsam - Anne Ober
- Matt Malloy - Harold Ober
- Bill Phillips - H.L. Mencken
- Tony Manna - Heywood Broun
- Sarah Ellen Stephens - Ritz Bathroom Attendant
- Deborah Offner - Miss Hunnycut
- Jordan Dean - Ludlow Fowler
- Cameron Scoggins - Harvey Firestone
- Conor Donovan - Lawrence Calderwood
- Ian Jarvis - Biltmore Hotel Manager
- Robert Vincent Smith - Monty
- Randy Kovitz - Professor Gauss
- Andrew Haserlat - Clerk
- Fred Tolliver Jr. - Bellboy
- Holly Curran - Tilde Sayre
- Joel Brady - Edmund Wilson
- Donna Mitchell - Marianne
- Kristine Nielsen - Minnie Sayre
- AJ Cedeno - John Sellers
- Jim True-Frost - Max Perkins
- Corey Cott - Townsend Martin
- Andrew Call - Reed
- Christina Bennett Lind - Tallulah Bankhead
- Natalie Knepp - Eugenia Bankhead
- Lucy Walters - Edna St. Vincent Millay
- Jun Naito - Tana Fujimora
- Bret Lada - Martini Maker
- Donté Bonner - Man
- Sharina Martin - Woman
- Gene Jones - Clerk
- Linda Atkinson - Movie Patron
- Christina Ricci
Christina Ricci interpreta a Zelda Fitzgerald en la serie.
David Hoflin interpreta a F. Scott Fitzgerald en la serie.
David Strathairn hace el papel de Anthony Sayre.
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