Guest Stars David Meunier as Johnny Crowder Jeremy Davies as Dickie Bennett Kaitlyn Dever as Loretta McCready William Ragsdale as Gary Hawkins Joseph Lyle Taylor as Doyle Bennett Margo Martindale as Mags Bennett Linda Gehringer as Helen Givens Kevin Rankin as Devil Richard Speight, Jr. as Jed Berwind Mark Colson as Hobart Curtis Co Starring Rebecca Metz as Emily Brian Allen as Player #2 James Logan as Player #1 Matt Riedy as Owner Mandy McMillian as Winona's Lawyer Sean Smith as Gary's Lawyer