Guest Stars James Wolk as Joe Keene Adelynn Spoon as Emma Abar Lily Rose Smith as Rosie Abar Frances Fisher as Jane Crawford Don Johnson as Judd Crawford Jolie Hoang-Rappaport as Bian Cheyenne Jackson as Hooded Justice (American Hero Story) Robert Wisdom as Seymour Jim Beaver as Andy Co Starring Danny Boyd Jr. as Young Will Reeves Steven Gregory Norfleet as O.B. Williams Henry Louis Gates Jr. as Skip Gates Brian Stapf as Tattooed Man Luke David Blumm as Newspaper Boy Kate Kovach as Dame Faye Yvette McQueen as Fashionable Lady Vince Pisani as Cashier Christian Robinson as Delivery Guy Ryan Czerwonko as Ringleader Annika Pampel as Fraulein Mueller Moses J. Moseley as Usher Jim Braswell as Singer Miles Doleac as German Officer Tevin Marbeth as Soldier