Matthew Weiner Director, Screenwriter, Producer Owen Wilson Steve Dallas Actor Zach Galifianakis Ben Baker Actor Amy Poehler Terry Coulter Actor Laura Ramsey Angela Baker Actor Alana De La Garza Victoria Rio Lobos Actor Joel Gretsch Red Coulter Actor Paul Schulze Dave Harken Actor Edward Herrmann Dr. Vincent Actor Peter Bogdanovich Judge Harlan Plath Actor David Selby Karl Stevens Actor Lauren Lapkus Delia Shepard Actor Greg Cromer Kyle Robertson Actor Jenna Fischer Alli Actor Gary Gilbert Producer Jordan Horowitz Producer Scott Hornbacher Producer Keith Addis Executive Producer Chris Manley Cinematographer Christopher Gay Film Editing David Carbonara Original Music Dan Bishop Production Design David Morong Art Director Carla Curry Set Decoration Wendy Chuck Costume Design Laura Schiff Casting Carrie Audino Casting