Guest Stars Chris Chalk as Gary Cooper Adina Porter as Kendra James Marcia Gay Harden as Rebecca Halliday B.J. Novak as Lucas Pruit Brian Howe as Barry Lasenthal Jon Bass as Bree Dorrit Kevin Rankin as Cellmate Sarah Sutherland as Mary Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Trieu Tran as Joey Phan Thomas Matthews as Martin Stallworth Wynn Everett as Tamara Hart Riley Voelkel as Jennifer "Jenna" Johnson Sarah Scott Davis as Terry Smith John Hawkinson as Rudy Frank Cermak. as ACN Digital Staffer Luke Margarita Kallas as Flight Attendant Terence Leclere as Photographer Ilana Guralnik as Honeymoon Woman Michael Ark as Honeymoon Man Anna Trebunskaya as Ticket Agent James Holloway as Guard Nelson Cheng as Rebecca's Assistant Francisco Javier Gomez as Man on Plane