- Adam Capriolo - Chris Kanew
- Felicia Shulman - Cherie Parkinson
- Jane Wheeler - Harvard Mother
- Karl Graboshas - Admission Officer
- Jonah Carson - Busker
- Susan Glover - Female Professor
- Meghan Gabruch - Azalia's Hostess
- Kenny Wong - Mark
- Keir Cutler - TSA Officer
- Erin Agostino - Flight Attendant
- Shauna Bradley - Diane Fisher
- Frank Fontaine - Older Man
- Carolyn Fe - Chinese Waitress
- Izzy Stannard - Tween One
- Dawn Ford - Jason's Executive Assistant
- Rosalba Martinni - Older Latina
- Spiro Malandrakis - Bartender
- Xavier Sotelo - Harvard Father
- Adam Bernett - Ticket Seller
- Alex Bisping - Beta Male #1
- André Simoneau - Beta Male #2
- Ivan Fuchs - George
- Allison Williams - Troy's Girlfriend
- Raynnie Platz - Jason's Child #3
- Jimmy Kimmel - Self
- Danielle Lyons - College Tour Guide (uncredited)
-
Mike White
- Brad Pitt
- Fabiana Arrastia
- Mike White
- Bruce Toll
- Katie Doyle
- Sidney Kimmel
- Joshua Adeniji
- Mark Mothersbaugh
- Albert Fox
- John Enroth
- James Parnell
Capítulo disponible en las siguientes plataformas: