Guest Stars Maulik Pancholy as Jonathan Jason Sudeikis as Floyd DeBarber Emily Mortimer as Phoebe Co Starring Kevin Brown as Walter "Dot Com" Slattery Grizz Chapman as Warren "Grizz" Griswold Lester Holt as Himself Justin Smith as Black Crusader Eric Dysart as Alan Garkel Mira Tzur as Receptionist Gregory Korostishevsky as Russian Julian Walker as Nice Cleveland Person Ramsey Faragallah as Sheik Brian Patrick Russell as Cleveland Cop Jack Moran as Cleveland Vendor Jenelle Malbrough as Bratty Kid Gary Tacon as Crazy Homeless Guy Lori Hammel as Cleveland Woman Jennifer Bassey as Old Vibrant Lady Anthony Mazza as NYC Cop Raymond McAnally as Cleveland Dude Traci Hovel as Broker Mitch Poulos as TV Station Man