Guest Stars Josh Stamberg as Bill Shine Mackenzie Astin as John Moody Patch Darragh as Sean Hannity Guy Boyd as Chet Collier John Finn as Jack Welch Jamie Jackson as Ian Rae Co Starring Orlagh Cassidy as Stephanie Rains Kaye Tuckerman as Australian Executive Twinkle Burke as Waitress Meredyth Kenney as Female Anchor Charlie Franklin as Young Producer 1 Matt Crabtree as Smart Liberal Nicholas Baroudi as Male Anchor Ben Rameaka as Late Executive Tanya Rivero as Correspondent Stephen James Anthony as Young Producer 2 Hayley Griffith as Chloe Jesse Cord Weber as Reporter 1