- Gus Halper - Joseph Lyman
- Matt Lauria - Ben Newton
- Jason Mantzoukas - Bee (voice)
- Warren Katz - Minister
- John Mulaney - Henry David Thoreau
- James Urbaniak - Ophthalmologist
- Anna O'Donoghue - Loud Woman
- Olivia Khoshatefeh - Young Woman #1
- Manuela Sosa - Young Woman #2
- Timothy Simons - Frederick Law Olmsted
- Jibz Cameron - Sanford Robinson Gifford
- Kelli Barrett - Adelaide May
- Curtis Bannister - Opera Chorus Member 1
- Ron Crawford - Usher
- Jessica Hecht - Aunt Lavinia
- Jen Ponton - Body Healer
- Nick Kroll - Edgar Allan Poe
- Ade Otukoya - Henry 'Box' Brown
- Omar Shaukat - Townie 1
- Tim Simon - Townie 2
- Tatiana Marie Barber - Activist / Dancer
- Teddy Bergman - Minister
- Teddy Bergman - Daniel Bliss
- Marquis Floyd - Dancer
- Nerita McFarlane - Dancer
- Imani Wisdom - Dancer
- Marié Botha - Mary Bowles
- Brendan Dalton - Sylvester
- Finn Jones - Samuel Bowles
- Pico Alexander - Henry 'Ship' Shipley
- Ayo Edebiri - Hattie
- David Manis - Minister
- Roland Sands - Old Man
- Gus Birney - Jane Humphrey
- Billy Eichner - Walt Whitman
- Zosia Mamet - Louisa May Alcott
- Beth Ditto - Pfaff's Dancer
- Anthony R. Mottola - Wounded Soldier
- Mariah Naomi Sanchez - Nurse
- Emily Kramm - Pfaff's Dancer #1
- Tómas Matos - Pfaff's Dancer #7
- Emily Dorsch - Auctioneer
- Nandita Shenoy - Woman
- Will Pullen - Nobody
- Will Pullen - Frazar Stearns
- Jordan Lage - Asylum Head Doctor
- Marceline Hugot - Asylum Patient
- Annie Hamilton - Florence
- Morgan Sullivan - Soldier
- Casey Jane Ellison - Doll Woman
- Sibyl Santiago - Nurse
- Alexio Barboza - Dancer
- Ziwe Fumudoh - Sojourner Truth
- Chloe Fineman - Sylvia Plath
- Samuel Farnsworth - George Gould
- Kevin Yee - Toshiaki
- Sophie Zucker - Abby Wood
- Robert Picardo - Ithamar Conkey
- Wiz Khalifa - Death
- Darlene Hunt - Maggie
- Erin Gerasimovich - Anna
- Max Chernin - Samuel Strong
- Gabriel Ebert - Thomas Wentworth Higginson
- Nore Davis - Solomon
- Myles Evans - Erasmus
- Tristan Griffin - Everett
- Wavyy Jonez - The Wall
- Mirella Cardoso - Mermaid #1
- Kathy Liu - Mermaid #4
- Natalie Von Kirk - Mermaid #5
- Jeremy Lawrence - Professor Hitchcock
- Peggy Cosgrave - Mrs. Thoreau
- Vince Edgehill - Conductor
- Lucas Near-Verbrugghe - James
- Michael Braun - Thomas Elliott Moody
- Peter Maloney - Doctor Brewster
- John Leonard Thompson - Mr. Humphrey
- Dee Hoty - Mrs. Humphrey
- Jason Williams - Dancer
Capítulo disponible en las siguientes plataformas:
