Special Guest Stars John McEnroe as Himself Guest Stars Keith Powell as James "Toofer" Spurlock Katrina Bowden as Cerie Maulik Pancholy as Jonathan Lonny Ross as Josh Girard Peter Hermann as Gray Brian McCann as The Head Co Starring Teddy Coluca as Stage Manager Craig Castaldo as Moonvest Rock Kohli as Store Clerk J.T. Arbogast as Contestant #1 Tyler Johnson as Model/Waiter Michal Antonov as 10 Year Old Liz Nikki Ghisel as MSMBC Receptionist Ali Reza as Executive Brendan Walsh as Shut It Down Jon Norman Schneider as Contestant #4 Carrie Yaeger as Contestant #2 Audrey K. Amey as Contestant #3 Uncredited Marcus Collins as The Hair