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Jon Hamm Tom Adkins Sr. Josh Lucas Matthew Wakefield Rhona Mitra Barbara James Van Der Beek Diploma / Roggiani Jessica Chastain Sally Ann Joanna Cassidy Lea Adkins Jimmy Bennett John Morena Baccarin Rose Montgomery Michael Cudlitz Jonas Beth Grant Older Edvena Holt McCallany Swede Andy Milder William Daniels Jude Ciccolella Police Chief Rick Gomez Officer JJ Marcus Thomas Pete Dunne Graham Phillips Mark Wakefield Kali Rocha Coral Sam Hennings Older Luke Wakefield Tom Kemp Russell MacArthur Benjamin Burdick George Montgomery Kim Hamilton Miz Betsy Bob Stephenson Mike the Bartender William Charles Mitchell Lou Glenn Taranto Chollie Ryan Cutrona Bill Byrnes Ty Panitz Tommy Jr. Ray Proscia Lawyer Elizabeth Small Edvena Enuka Okuma Officer Angie Riddick Angela Schnaible Girl Jeanette Brox Lisa Kasey Campbell Micha Cheyenne Wilbur Old Minister Pamela Dunlap Shelly the Waitress Rutanya Alda Older Sally Ann James Mathers Joel Schubert Paul Keith Barber Jonathan Erickson Eisley Mick Channing Chase Lorraine Charles C. Stevenson Jr. Man Getting a Cut Bart McCarthy Kevin Byrnes Tonye Patano Elsie Mauer Beresford Bennett Investigator Al Corley Uncle Sam