Guest Stars Chris Chalk as Gary Cooper Grace Gummer as Hallie Shea Marcia Gay Harden as Rebecca Halliday Hamish Linklater as Jerry Dantana Constance Zimmer as Taylor Warren Hope Davis as Nina Howard Patrick Fabian as Tony Hart Stephen Root as General Stomtonovich Merle Dandridge as Maria Guerrero Melanie Papalia as Aubrey Lyons Co Starring Margaret Judson as Tess Westin John F. Carpenter as Herb Wilson Trieu Tran as Joey Phan Charlie Weirauch as Jake Watson Nick Gehlfuss as Ross Kessler Andy Wagner as Ken Weinraub Marque Richardson II as Mark Gage Cherie Daly as Chelsea Daniel Brunnemer Hall as Man in Bar Walter Gray IV as Devon Francisco Rodriguez as Crew Member Carrie Malabre as Waitress Drew Wicks as Randall Dell