Guest Stars Daniel Roebuck as Nick Bledsoe Andrew Rothenberg as Eddy Sanderson Dana Gould as Tug Purcell John Pollono as Pat Dolan Michael McGrady as Chief Clemance Horall Richard Brake as Terry Iddo Goldberg as Leslie Shermer Mike Hagerty as Fat Jack Bray Jeremy Strong as Mike Hendry Mekia Cox as Anya Simon Pegg as Hecky Nash James Landry Hébert as Miles Hewitt Stephen Monroe Taylor as Phil Holtz Co Starring Ryan Dorsey as Young Sid Jake Lockett as Young Bugsy Devon Coull as Thug #2 Josh Fingerhut as Wounded Man Bix Barnaba as Jimmy Delaney Jeff Braine as Young Meyer Johnny Cannizzaro as Thug #1 Annika Pampel as Stripper