- Luzer Twersky - Mendel
- Mel Shimkovitz - Jude
- Lena Waithe - Jane
- Zander Faden - Young Josh
- Nathan Fielder - Seth
- Courtney Hope - Una
- Ray Abruzzo - Sal
- Didi Conn - Joyce Feldman
- Cass Buggé - Georgia
- Hari Nef - Gittel
- Richard Masur - Buzzy Rackless
- Mitch Rouse - Richard
- Peaches - Peaches
- Sia - Puppet
- Jiz Lee - Pony
- Eileen Myles - Rae Riordan
- Devendra Banhart - Wolfgang
- Anjelica Huston - Vicki
- Our Lady J - Yorna
- Our Lady J - Miss Pico-Union
- Elisha Henig - Young Simon
- Molly Bernard - Younger Shelly
- Candis Cayne - Jolene
- Rain Valdez - Miss Van Nuys
- Angelica Ross - Diana Ross Diva
- Cherry Jones - Leslie Mackinaw
- Jenny O'Hara - Bryna
- Jerry Adler - Moshe Pfefferman
- Bashir Naim - Simon
- Richard Kind - Howard
- Alia Shawkat - Lila
- Rainn Wilson - Arthur
- Danny Dolan - Jesus
- Erik Liberman - Jeff
- Folake Olowofoyeku - Lyfe
- Paul Tigue - Nesim
- Alison Sudol - Kaya
- Juana Samayoa - Avalea
- Sawyer Ever - Zack Novak
- Sonal Shah - Female Student
- Stanley Ullman - Deli Man
- Cleo Anthony - Derek
- Amin Joseph - Mike
- Zackary Arthur - Zack
- Zackary Arthur - Zacky
- Zackary Arthur - Zack Pfifferman
- Makenna James - Young Sarah
- Cleo Fraser - Young Ali
- Arabella Anderson - Kit
- Ethan Sandler - Barry
- Ethan Kuperberg - Clive
- Jack Topalian - Tigran
- Tig Notaro - Barb
- Elaine Hendrix - Mom
- Bruce Daniels - Ronny
- Bradley Whitford - Macy
- Bradley Whitford - Magnus
- Michaela Watkins - Connie
- Michaela Watkins - Yetta
- Kurtis Bedford - Desk Clerk
- Hank Chen - Clayton
- Daniel Robaire - Brad
- Zackary Drucker - Eleanor
- Zackary Drucker - Group Leader
- Luke Sholl - Chad
- Corey Allen Kotler - Manager Joe
- Deborah S. Craig - Kristin
- John Kapelos - Gary
- Melia Renee - Pixie
- Stephanie Carrie - Host
- Rhys Ernst - Waiter
- Holly Woodlawn - Vivian
- Alexis Del Lago - Bernadette
- Faith Soloway - Cantor Joy
- Faith Soloway - Shmuley
- Joey Soloway - Celeste
- William Martin Brennan - Victor
- Van Barnes - Houston T-Girl
- Ian Harvie - Dale
- Jason Mantzoukas - Dr. Steve
- Petey Gibson - Butch Slam Poet
- D'Lo - MC Mama's Boi
- Trace Lysette - Shea
- Roxy Wood - Roxy
- James Frecheville - Patrick
- Pat Towne - Jackie
- Leonardo Ciacci - Stella
- Annabel Marshall-Roth - Young Rita
- Vico Ortiz - Cindy
- Kathryn Hahn - Raquel Fein
- Carrie Brownstein - Syd Feldman
- Alexandra Billings - Davina
- Alex MacNicoll - Colton
- Rob Huebel - Len Novak
- Lawrence Pressman - Ed Paskowitz
- Kiersey Clemons - Bianca
- Caroline Aaron - Judy
- Emily Robinson - Ali 12 Years
- Kelsey Reinhardt - Sarah 18 Years
- Abby Ryder Fortson - Ella Novak
- Brett Paesel - Rita Holt
- Alyvia Alyn Lind - Grace
- Corey Podell - Gail
- David Futernick - David
- Noah Harpster - Francis
- Ali Liebegott - Tiffany
- Gail Silver - Ruth
- Bryna Weiss - Esther
- William Goldman - Jim Cashman
- Chloe Coleman - Idit Ovadia
- Ruby Matenko - Young Bryna
- Karim Saleh - Hussen
- So Yong Kim
- Jim Frohna
- Sarah Gavron
- Allison Liddi-Brown
- Marielle Heller
- Gaby Hoffmann
- Gabe Liedman
- Bridget Bedard
- Jessi Klein
- Noah Harpster
- Micah Fitzerman-Blue
- Ali Liebegott
- Sam Patton
- Rick Rosenthal
- James Parnell
Jeffrey Tambor hace el papel de Maura Pfefferman.
Caroline Aaron hace el papel de Judy.
Jenny O'Hara interpreta a Bryna en la serie.
Gaby Hoffmann interpreta a Ali Pfefferman en la serie.
Melora Hardin hace el papel de Tammy Cashman.
Cherry Jones interpreta a Leslie Mackinaw en la serie.
Amy Landecker hace el papel de Sarah Pfefferman.
Judith Light hace el papel de Shelly Pfefferman.
Capítulo disponible en las siguientes plataformas:
