Air date 11/15/2023
| Joshua Ray Walker | Believe |
| Kathleen Edwards | Glenfern |
| Billy Joe Shaver | Ragged Old Truck |
| Ernest Tubb | Thanks A Lot |
| Junior Brown | Venom Wearin’ Denim |
| Jean Shepard | Second Fiddle (To an Old Guitar) |
| Wanda Jackson | Two Shots |
| Merle Haggard | The Way I Am |
| Ray Price | Night Life |
| Kris Kristofferson | The Silver Tongued Devil and I |
| Emmylou Harris | Pancho and Lefty |
| Luke Bell | The Glory and the Grace |
| Jerry Jeff Walker | Little Bird |
| Tom T. Hall | Faster Horses (The Cowboy and the Poet) |
| Ray Wylie Hubbard | Conversation with the Devil |
| Johnny Cash | In My Life |
| Hank Williams | Kaw-Liga |
