| Feel This Right | Jeremy Pinnell | 3:20 | |
| Misery and Gin | Jaime Wyatt | 4:24 | |
| Bernadine (feat. Chris Carroll) | Adam Carroll, Chris Carroll | 4:31 | |
| Bear Creek Blues | John Prine | 4:45 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Paper Cowboy | Margo Price | 6:15 | |
| True Blue | Pat Reedy | 2:28 | |
| I'm Broke | Croy and the Boys | 2:52 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Earthly Justice | Western Centuries | 4:03 | |
| Off This Mountaintop | Ian Noe | 3:32 | |
| Highway 46 | Tom Russell | 4:05 | |
| On the Ropes | The Honeycutters | 3:15 | |
| All Blue | Luke Bell | 3:21 | |
| Call Yourself My Man | Hannah Juanita | 3:56 | |
| January in Louisiana | Fifth On The Floor | 3:20 | |
| No Later than Soon | Jim Lauderdale | 2:56 | |
| Herding Song | Riddy Arman | 2:07 | |
| She Took A Lot Of Pills (And Died) | Robbie Fulks | 2:43 | |
| I Left My One Spot (Back at the 5 Spot) | Elijah Ocean | 3:00 | |
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| If I Were a Carpenter (feat. Kelsey Waldon) | JP Harris, Kelsey Waldon | 3:10 | |
| Outlaw Life | Jeremy Pinnell | 3:43 | |
| Tennessee Song | Margo Price | 4:40 | |
| My Failing Life | Dylan Earl | 3:17 | |
| Knee Deep in the Wakarusa River | Chuck Mead | 3:29 | |
| Die Midwestern | Arlo McKinley | 4:09 | |
| Loretta | Luke Bell | 3:58 | |
| When The Wheels Touch Down | Wrinkle Neck Mules | 4:11 | |
| This Changes Everything | Jim Lauderdale | 3:32 | |
| I'm Alright With This | Jeremy Pinnell | 3:59 | |
| Anyhow | Kelsey Waldon | 2:58 | |
| Pill Bug Blues | The Gourds | 3:59 | |
| Methadone Blues | Elizabeth Cook | 3:43 | |
| Wherever You Go | Dee White | 3:20 | |
| As Young as You'll Ever Be | Paul Cauthen | 3:40 | |
| Strip Job Blues 1984 | Ian Noe | 3:25 | |
| Lorene | Brent Cobb | 2:23 | |
| Panicked and Paralyzed | Chris Acker | 4:42 | |
| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| Are They Gonna Make Us Outlaws Again | Gus Clark & the Least of His Problems | 4:12 | |
| I Sang The Song | Mac Wiseman, John Prine, Peter Cooper, Thomm Jutz | 3:35 | |
| Paid My Dues (feat. Jack Ingram) | Bruce Robison, Jack Ingram | 3:22 | |
| Good As Gold | Sarah Shook & the Disarmers | 3:13 | |
| Perfect Timing | Drive-By Truckers | 2:57 | |
| James Alley Blues | Willie Watson | 4:06 | |
| Hobo Cartoon | Sturgill Simpson | 2:32 | |
| The Highway Less Taken | Justin Wells | 3:22 | |
| Mexican Home (feat. John Prine) | Chris Knight, John Prine | 5:05 | |