Special Guest Stars Allison Tolman as Deputy Molly Solverson Colin Hanks as Deputy Gus Grimly Joey King as Greta Grimly Keith Carradine as Lou Solverson Guest Stars Bokeem Woodbine as Mike Milligan Cristin Milioti as Betsy Solverson Zahn McClarnon as Hanzee Dent Angus Sampson as Bear Gerhardt Rachel Keller as Simone Gerhardt Michael Hogan as Otto Gerhardt Keir O'Donnell as Ben Schmidt Ryan O'Nan as Ricky G Co Starring Brad Mann as Gale Kitchen Emily Haine as Noreen Vanderslice Raven Stewart as Molly Solverson Wilma Pelly as Native American House Keeper Adam Arkin as Hamish Broker Philip Williams as The Book Thomas Rayment as Bully #1 Will Simpson as Bully #2 Arielle Rombough as Teacher Libby Seltzer as Molly 12 Yrs Laura Geluch as Molly 18 Yrs Dennis Corrie as Old Man Artem Fomitchev as Grady Corwin Gruter-Andrew as Wes Cameron Hamilton as Grimly Son Terry A. Brown as Grover Littlejohn