Guest Stars DeRon Horton as Hilliard "Hilly" Percy Daggs IV as Pity Martin Bradford as Billy Freres Denise Burse as Shirley Wring Co Starring Katina Rankin as Newscaster Breanna Allen as Melinda Hogarth Jul Kohler as Olga Lorenzo Yearby as Jocko Jackie Renee Robinson as Homeless Woman Mallory Hoff as Newscaster Ryan Kowalske as Sales Clerk David J. Turner as Homeless Man