Joe Kwaczala
— Jay Christopher / Jovan
Sam Wiles
— Dan
John Eisenrich
— Jay's Biggest Fan
Hayley McFarland
— Olivia
Patton Oswalt
— Himself
Doug Benson
— Bryan Gold
Liezl Estipona
— Photographer #1
Jack Robichaud
— Jack
Trevor Martin
— Outside Comic #1
Jon Millstein
— Outside Comic #2
Lindsay Adams
— Outside Comic #3
Conor Sullivan
— Outside Comic #4
Simon Gibson
— DHB Podcast Guest
Katherine Blanford
— Riffing Comic #1
Ryan O'Flanagan
— Bowtie Ryan
Will A. Miles
— Riffing Comic #2
Amy Miller
— Riffing Comic #3
Alison Stevenson
— Alison
Sharmita Bhattacharya
— Leela
Cleveland Anderson
— Drop-in Show Host
Cameron Gillette
— Cameron
Kristen Studard
— Photographer #2
Kaitlyn Tanimoto
— Comedy Club Waitress
Christina Catherine Martinez
— Green Room Comic #1
Biniam Bizuneh
— Green Room Comic #2
Alyssa Limperis
— Green Room Comic #3
Derek Scully
— "Kevin Green" Heckler
Christine Medrano
— Chicago Open Mic Host #1
Nori Reed
— Chicago Open Mic Host #2
Meredith Kachel
— "Try Being Funny" Heckler