| Time Honored Tradition | Natalie Hemby | 3:16 | ||
| How It Goes (feat. Jon Berry & Courtney Marie Andrews) | Asher Deaver, Courtney Marie Andrews, Jon Berry | 3:33 | ||
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | ||
| From Outer Space | Jaime Wyatt | 4:13 | ||
| Christchurch Woman | Justin Townes Earle | 4:11 | ||
| Tangletown | Craig Finn | 4:30 | ||
| Years | Sarah Shook & the Disarmers | 3:35 | ||
| Tennessee (feat. Courtney Marie Andrews & Jon Berry) | Asher Deaver, Courtney Marie Andrews, Jon Berry | 2:46 | ||
| Woman of Many Colors | Courtney Marie Andrews | 3:10 | ||
| Getting It Right | Caitlin Rose, Courtney Marie Andrews | 2:50 | ||
| Only One | Sera Cahoone | 3:17 | ||
| Dirtbag Saloon | Emily Scott Robinson | 4:12 | ||
| Middle Child | Daniel Romano | 3:48 | ||
| The Trip | Dave Rawlings Machine | 10:55 | ||
| I Could've Been Your Lover Too | Rachel Baiman | 3:09 | ||
| End of the Line | Hurray For The Riff Raff | 3:38 | ||
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 |