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 James Logan as Player #1 Rebecca Metz as Emily Matt Riedy as Owner Brian Allen as Player #2 Mandy McMillian as Winona's Lawyer Sean Smith as Gary's Lawyer