Guest Stars Dominic Chianese as Leander Cephas Whitlock Margot Bingham as Daughter Maitland Ben Rosenfield as William H. "Willie" Thompson Patricia Arquette as Sally Wheet Brian Geraghty as Agent Warren Knox / Jim Tolliver Stephen Root as Gaston Means Louis Gossett, Jr. as Oscar Boneau Co Starring Brady Noon as Tommy Darmody Connor Noon as Tommy Darmody Nisi Sturgis as June Thompson Brandon Zumsteg as Brian Thompson Charlie Plummer as Michael Thompson Emma Holzer as Edith Thompson Madeline Getty as Nora Thompson Steve Beauchamp as Sid Lola Freidenstine as Anne Thompson David McElwee as Roger's Friend Brian Tyree Henry as Winston 'Scrapper' Brian D. Coats as Levi Warren Kelley as David Hewson D'Monroe as Weems Bob Sorenson as John Ferry