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 Iddo Goldberg as Leslie Shermer Richard Brake as Terry Mike Hagerty as Fat Jack Bray Jeremy Strong as Mike Hendry Gordon Clapp as Carl Steckler Simon Pegg as Hecky Nash James Landry Hébert as Miles Hewitt Micah Joe Parker as Moe Feltzer Brendan Sexton III as Jerry Edelstein Stephen Monroe Taylor as Phil Holtz Michael Ornstein as Ray Berman Andrew Fiscella as Harvey Weber Matt Cook as Huey Ian Reed Kesler as Louie Richard Riehle as Sergeant Kuzyk David Warshofsky as Sol Lipsky Scott MacDonald as Dewey Co Starring Louis Lombardi as Stucky Fein Colleen Camp as Woman in Restaurant Phillip DeVona as Sam Robert Riechel, Jr. as Izzy Michael Mallory as Greenie