Guest Stars David Alford as Bucky Dawes Kourtney Hansen as Emily Joseph David-Jones as Clayton Carter Linds Edwards as Carl Hockney Jordan Woods-Robinson as Randall St. Claire Bridgit Mendler as Ashley Willerman Co Starring Rhiannon Giddens as Hanna Lee "Hallie" Jordan Liz McGeever as Studio Assistant Morgan Bonner as Posse Member #1 D'Kia Anderson as Posse Member #2 Kyle Austin Rhodes as Barista