| Pain Pills | Angaleena Presley | 2:58 | |
| Bad Boy | John Prine | 3:27 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| These Blues | Eilen Jewell | 2:45 | |
| Yes to Booty | Elizabeth Cook | 2:04 | |
| I Can't Wait | Kieran Kane, Kevin Welch, Fats Kaplin | 3:31 | |
| Time After All | Sturgill Simpson | 2:37 | |
| Wreck You | Lori McKenna | 3:18 | |
| Hold On I | Chris Smither | 4:03 | |
| Nine Volt Heart | Dave Alvin | 4:57 | |
| If I Could Make You My Own | Dori Freeman | 3:22 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| I Thought the Wreck Was Over | The Flatlanders | 2:45 | |
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | |
| Humble & Kind | Lori McKenna | 4:03 | |
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | |
| Lookin' Back on Luckenbach | Whitney Rose | 4:17 | |
| Just Like Heartache | Jamie Lin Wilson | 3:40 | |
| Streets of Baltimore - 2007 Remaster | Gram Parsons | 2:55 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Can't Get Home | Steep Canyon Rangers | 3:29 | |
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| You Never Even Call Me By My Name | Steve Goodman | 4:19 | |
| Better to My Baby | Whitney Rose | 3:11 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| Going Back to Georgia | Nanci Griffith | 4:16 | |
| Bohemian Wedding Song | Shannon McNally | 5:49 | |
| Instant Coffee Blues | Jamie Lin Wilson, Jack Ingram | 3:25 | |
| Oh Soul | Mary Gauthier | 5:26 | |
| Lisa's Birthday | Drive-By Truckers | 3:19 | |
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Settle Down | Holly Williams, Southern Family | 2:27 | |
| Never Cry Again | John Fullbright | 4:14 | |
| Our Love Is Done | Hannah Juanita | 4:12 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Dopamine Dream | Wrinkle Neck Mules | 3:50 | |
| Time Stands Still | Chris Smither | 3:45 | |
| Everybody's Moving Slow | Jamie Lin Wilson | 3:27 | |
| Eden | Amanda Anne Platt & the Honeycutters | 5:32 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Adios Maria | The Cactus Blossoms | 4:09 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| Far from Me | John Prine | 5:09 | |
| Lonesome Blues | Shooter Jennings | 3:59 | |
| Alcohol And Pills | Fred Eaglesmith | 3:58 | |
| The Hardest Part | Allison Moorer | 3:13 | |
| Fourth Of July | Dave Alvin | 4:35 | |
| Love At The Five & Dime | Nanci Griffith | 4:39 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |