- Luke Kirby - Lenny Bruce
- Jane Lynch - Sophie Lennon
- Caitlin McGee - Vonnie
- Gilbert Gottfried - Strip Club MC
- Emily Price - Fan Girl
- Tansy - Stripper
- Richie Allan - Irv
- Joel Rooks - Lutzi Neiderman
- Barbara Miluski - Lady Customer
- Victor Verhaeghe - Antonio
- Mike Rosengarten - 'Sixteen Tons' Trio
- Aime Donna Kelly - Janet Shaw
- Haleigh Ciel - Blonde in Front Row
- Benjamin Mapp - Beatnik
- Matthew Hammond - Bathroom Guy
- Laura Shoop - Upper West Side Woman
- Jonathan Randell Silver - Audience Member
- Mike Massimino - Officer Peluso
- Gina Costigan - Officer Judy
- Keilly McQuail - Tracy
- Max Azulay - Partygoer
- Caitlin Mehner - Honey Bruce
- Kelsey Carthew - Greta
- Kate Wetherhead - Polly
- Jaxon Folds - 10-Year-Old Boy
- Arielle Goldman - Eliana
- Michael Iacono - Boy Scout
- Adam B. Shapiro - Cantor
- Eric William Morris - 'Sixteen Tons' Trio
- Meghan Manning - USO Canteen Dancer
- Claire Friesen - Performer
- Milo Ventimiglia - Sylvio
- Lisandro Boccacci - Hotel Conceirge (uncredited)
- Matthew Jeffers - Russell
- Hari Nef - L. Roy Dunham
- Ashlie Atkinson - Peggy
- Domenick Lombardozzi - Mr. Bartosiewicz
- Joel Johnstone - Archie Cleary
- Gideon Glick - Alfie
- Stephanie Hsu - Mei
- David Paymer - Harry Drake
- Jason Alexander - Asher Friedman
- Saul Rubinek - Pauly Auerbach
- Peter Gerety - Clifford
- Max Casella - Michael Kessler
- John Scurti - Nicky
- Erik Palladino - Frank
- Scott Cohen - Solomon Melamid
- Ned Eisenberg - Lou Rabinowitz
- Jason Ralph - Mike Carr
- Leroy McClain - Shy Baldwin
- Andrea Boehlke - Girl Singer
- Jay Will - James
- Patrice Johnson - Miss Em
- Chris Eigeman - Gabe
- Katrine Hoyt - Mitzi
- Nina Arianda - Hedy
- Will Brill - Noah
- Justine Lupe - Astrid
- Peter Friedman - George
- Cynthia Darlow - Mrs. Moskowitz
- Matilda Szydagis - Zelda
- Gibson Frazier - Dr. Elie Klein
- Jim Lau - Mei's Father
- Colin Keane - Ethan
- Seaton Smith - Willie
- Peggy J. Scott - Verla
- Andrew Polk - Fred
- Alexandra Socha - 23-Year-Old Esther
- Alexandra Socha - 27-Year-Old Esther
- Callan Barry - Mike Carr's Kid
- Candyce Adkins - Gate Agent
- Maggie Weston - Woman
- Erica Mansfield - Tawny
- Veanne Cox - Corinne
- Currie Graham - Mike Wallace
- Annie Golden - Marge
- Lucy Taylor - Penelope
- Austin Basis - Alvin
- Zurin Villanueva - Waitress
- Zurin Villanueva - Lill
- Lucas Kavner - Cecil
- Eddie Kaye Thomas - Adam
- Michael Cyril Creighton - Mel
- Darlene Violette - Offended Woman
- Danny Doherty - Cop
- Malika Samuel - Dorie
- Chloë Kerwin - Trudy
- Steve Belanger - Policeman
- Kevin Pariseau - Terrence
- Alexander Blaise - Lance
- Alexander Gemignani - Janusz
- Alexander Gemignani - Old Man
- John Noble Barrack - Stage Manager
- Steve Greenstein - Toots Shor
- Kelly Bishop - Benedetta
- Emily Bergl - Tessie
- Julie Klausner - Maggie
- Joe Bacino - Bartender
- Daniel Hepner - Kibbutz Worker
- Al Cerullo - Helicopter Pilot
- Charlie Faith - Jimmy Breslin
- Ariel Kavoussi - Operator
- Teddy Coluca - Manny
- Bonnie Rose - Bubbie
- Yury Tsykun - Mysterious Man
- Alfred Rosenblatt - Mysterious Man
- Ariel Eliaz - Mysterious Man
- Bruce Sabath - Mysterious Man
- Noam Shapiro - Mysterious Man
- Yoni Lotan - Mysterious Man
- Matt W. Cody - Syd Greenberg
- Andy Lucien - John Coltrane
- Olivia Oguma - Office Girl
- Kerry Butler - Tuppance
- Robert Ray Manning Jr. - Toby
- Ethan Slater - Steven
- Alex Wyse - Jerome
- Ben Rosenfield - 30-Year-Old Ethan
- Ben Rosenfield - 29-Year-Old Ethan
- Jane Corcoran - Garbage Man
- Joel Blum - Bus Driver
- Jeffrey Bean - Carl
- Emily Morden - Tina
- Bruce Altman - David Weston
- Debra Monk - Helen Dyer
- Michael Barra - Lev
- Anne-Marie Cusson - Reverend Mother
- Charlotte Fountain-Jardim - Sister Clementine
- Betsy Helmer - Nancy
- Doug Goldring - Shelly
- Martin Harris - Piotr
- Tom Bentey - Man in a Towel
- Clark Carmichael - Tom
- Alex Cranmer - Darren
- Steve Routman - Alan
- Nili Bassman - Barbara
- Sean Gunn - Stewart Jones
- Danny Strong - Aaron Lebowitz
- Will Sasso - Carmine Streeto
- Danny Garcia - Ray Ortiz
- Darren Criss - Taylor
- Bailey De Young - Imogene Cleary
- Alanna Fox - Heather
- Jesse Sharp - Len Blixton
- Johnny Sanchez - Head Chef
- Pedro Saint Morillo - First Assistant Cook
- John Viener - Benny
- Tuffy Questell - Dennis
- Jason Babinsky - Tommy
- Chris Cafero - Cameron
- James Cribbins - Caddy
- Sebastian Beacon - Record Executive
- Renata Friedman - Ruth
- Christina Catechis - Linda
- Genesis Oliver - Dougie
- Elli - Cantor
- Adam Heller - Rabbi
- R.J. Foster - Agent Scanlon
- Todd Faulkner - King Swing
- Hank Azaria - Danny Stevens
- Sutton Foster - Carole
- Michael Torpey - Eugene
- Rob McClure - Pete
- Kevin Cahoon - Eddie
- Arden Myrin - Mrs. Moyers
- Patrick Shane - Kurt
- Mike Carlsen - Mr. Pinsky
- Julie Dolan - Mrs. Foster
- Elizabeth Inghram - Mother One
- Anna Fikhman - Mother Two
- Michael Bakkensen - Vic
- Allison Guinn - Bunny
- Alan Aisenberg - MC
- Brian J. Carter - Brian
- Sarah Steele - Petra
- Kenneth Tigar - Arthur
- Patrick Breen - Henry
- Dana Melanie - Daniella
- Rose Jackson Smith - Tammy
- Caitlin Houlahan - Kiki
- Barbara Andres - Letty
- Holly Curran - Penny Pann
- Joe Cummings - Mr. Dee
- Caroline Coleman - Sherry
- Alison Smith - Jane Jacobs
- Jeff Kready - John
- Helen Cespedes - Tracy
- Emmy Harrington - Sally
- Matt Bailey - Guy with Blonde
- Leslie Kritzer - Carol Burnett
- Pascale Armand - Delia
- Wenne Alton Davis - Cop
- Damian Muziani - Cop
- Meg Phillips - Meg
- Eric Berryman - Kev
- Miriam Silverman - Bernice
- Giuseppe Ardizzone - Cab Driver
- Joseph Bearese - Cab Driver
- Richard Gallagher - Alan Shepard
- Jeff Blumenkrantz - Wes
- Michael Hartung - Male Singer
- Ellen Doyle - Plum
- Anthony R. Mottola - Franklin
- Dillon Geyselaers - Heckler
- Pearls Daily - Maxine
- Kelvin Whui - Chinese Man
- Jason Furlani - Mario
- Lindsay Michelle Reed - Tea Room Patron (uncredited)
- Glen Raphael - Steiner Resort Singer
- Glen Raphael - Steiner Singer
- Brian Tarantina - Jackie
- Adam Keane - Astrid's Relative
- Sterling K. Brown - Reggie
- Geoffrey J.D. Payne - Military Officer
- David Rosenberg - David Ben Nasan
- Anaïs Blake - Dancer (uncredited)
- Gordana Rashovich - Helda
- Devon Bostick - Alan
Brian Tarantina interpreta a Jackie en la serie.
Saul Rubinek hace el papel de Pauly Auerbach.
Jason Alexander hace el papel de Asher Friedman.
Peter Gerety hace el papel de Clifford.
Kelly Bishop interpreta a Benedetta en la serie.
John Scurti hace el papel de Nicky.
Rachel Brosnahan hace el papel de Miriam 'Midge' Maisel.
Alex Borstein interpreta a Susie Myerson en la serie.
Michael Zegen interpreta a Joel Maisel en la serie.
Tony Shalhoub interpreta a Abe Weissman en la serie.
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