| Ditch | Sam Baker | 1:56 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Lazy Third Eye | Willy Tea Taylor, The River Arkansas | 4:06 | |
| Sweet Tooth | Dave Rawlings Machine | 5:20 | |
| Never Tire of the Road | Rachel Baiman | 3:45 | |
| I Don't Care Anymore | Rodney Crowell | 4:28 | |
| Green, Green Rocky Road | Dave Van Ronk | 3:42 | |
| Wait A Minute | The Seldom Scene | 3:35 | |
| How Quickly Your Heart Mends | Courtney Marie Andrews | 3:45 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Step-Back Red | Cordovas | 4:01 | |
| Million Dollar Bill | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:03 | |
| Midnight Special | Willie Watson | 4:38 | |
| Walkin' | Phosphorescent | 3:44 | |
| Lights of Cheyenne | James McMurtry | 6:40 | |
| Mama | Lula Wiles | 3:18 | |
| Someone Singing with Me | Joe Purdy, Amber Rubarth | 4:02 | |
| Meet Me On the Mountain | Fruition & Grant Farm | 4:28 | |
| Once Upon A Time | Robert Bradley's Blackwater Surprise | 3:20 | |
| Big Men in the Sky | Watchhouse | 4:05 | |
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| James Alley Blues | Willie Watson | 4:06 | |
| Quite a Feelin' | Barna Howard | 4:09 | |
| Tell Old Bill | Dave Van Ronk | 4:24 | |
| Cold, Cold World | Blaze Foley | 3:23 | |
| Mountain Girl | Blue Mountain | 4:05 | |
| Save Me Jesus | Bobby Charles | 5:17 | |
| Wrong Way to Run | Willy Tea Taylor | 2:34 | |
| Take This Hammer (feat. The Fairfield Four) | Willie Watson, The Fairfield Four | 2:59 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| Helen's Restaurant | Daniel Romano | 2:43 | |
| Lonesome LA Cowboy | Mapache | 4:32 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Love Is Just A Wrecking Ball | Del Barber | 4:20 | |
| Tunnel of a Dream | TK & The Holy Know-Nothings | 6:50 | |
| Never Been a Captain | The Barr Brothers | 4:41 | |
| Souls Without Maps | Joseph Huber | 6:36 | |
| Chaos And Clothes | Jason Isbell and the 400 Unit | 3:34 | |
| Love Will Only Break Your Heart | The David Mayfield Parade | 2:53 | |
| Mayfly | Jeffrey Foucault | 3:34 | |
| Carmelita | Warren Zevon | 3:34 | |
| Mother Earth | Willie Watson | 3:36 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Never A Forced Smile | Daniel Romano | 4:04 | |
| Lindsey Button | David Rawlings | 5:03 | |
| The Maker | Willie Nelson | 5:08 | |
| Blue | The Jayhawks | 3:09 | |
| Dancing With The Women At The Bar | Whiskeytown | 4:38 | |
| Ballad Of Spider John | Willis Alan Ramsey | 4:18 | |