Guest Stars Daniel Roebuck as Nick Bledsoe Andrew Rothenberg as Eddy Sanderson Dana Gould as Tug Purcell John Pollono as Pat Dolan Iddo Goldberg as Leslie Shermer Michael McGrady as Chief Clemance Horall Mike Hagerty as Fat Jack Bray Richard Brake as Terry 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 Johnny Cannizzaro as Thug #1 Bix Barnaba as Jimmy Delaney Jeff Braine as Young Meyer Josh Fingerhut as Wounded Man Annika Pampel as Stripper