Guest Stars Bokeem Woodbine as Mike Milligan Timothy Olyphant as U.S. Marshal Dick "Deafy" Wickware Rodney L. Jones III as Satchel Cannon Kelsey Chow as Swanee Capps Glynn Turman as Doctor Senator J. Nicole Brooks as Buel Cannon Sean Fortunato as Antoon Dumini Andrew Rothenberg as Liev Moskowitz Tommaso Ragno as Donatello Fadda Edwin Lee Gibson as Lionel "Happy" Halloway Co Starring Brad Mann as Gale Kitchen Will Clinger as Snowman Jameson Braccioforte as Zero Fadda Nadia Simms as Pessimindle Cannon Hannah Love Jones as Florine Cannon Nick Dibrizzi, Jr. as Paolo Endrizzi Lucy Carapetyan as Nurse Tapley Eric Slater as Milvin Gillis Sana Selemon as Nadine Waitress Evan Mulrooney as Joe Bulo (20's) Ira Amyx as Owney "Yiddles" Milligan (40yrs) Laurent Crawford as Happy's Giant Henchman Jermaine Young as Banjo Rightway Leo Sharkey as Ari Moskowitz (11yrs) Zane Gee as Patrick Milligan (7yrs) Debo Balogun as Happy's Man #1 David Dowd as Happy's Man #2 Jermaine Johnson as African American Busboy Mark Vallarta as Jail Officer