| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| Tell The Engineer | Fred Eaglesmith | 3:59 | |
| Nine Volt Heart | Dave Alvin | 4:57 | |
| Lessons in Gravity | Amanda Anne Platt & the Honeycutters | 5:20 | |
| Worn | Natalie Hemby | 3:35 | |
| I'm Not the Fire | Michaela Anne | 3:04 | |
| The North Dakota Cowboy | Brennen Leigh | 2:42 | |
| Cold Cold Wind | Jeremy Pinnell | 4:12 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| Once More to the Lake | Ken Yates | 3:50 | |
| All the Way Around | Kris Delmhorst | 3:53 | |
| Paper Cowboy | Margo Price | 6:15 | |
| Keep the Home Fires Burnin' | Sarah Shook & the Disarmers | 3:03 | |
| Living With A Long Way To Go | Del Barber | 2:32 | |
| Philosophers and Fools | Western Centuries | 3:12 | |
| Over the Hill and Through the Woods | Lillie Mae | 3:17 | |
| Borrowed Smiles | Caleb Caudle | 3:10 | |
| Big Bright Light | The National Reserve | 3:48 | |
| One Love Song (feat. Sam Outlaw) | Michaela Anne | 2:57 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| All You Ever (Live) | Amanda Anne Platt & the Honeycutters | 5:37 | |
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| Ain't It The Truth | The Honeycutters | 3:45 | |
| Humble & Kind | Lori McKenna | 4:03 | |
| You Can't Be High | The Small Glories | 3:47 | |
| Southern Arms (feat. Adriel Denae) | Cory Chisel, Adriel Denae | 2:58 | |
| Hey Trouble | Will Kimbrough | 4:21 | |
| If Something Breaks | Front Country | 4:56 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| First Time in Years | Erik Koskinen | 3:52 | |
| Modern World | Kelly Willis | 2:27 | |
| Freewheeling | Buford Pope | 4:20 | |
| What's Goin' Wrong | Justin Townes Earle | 3:25 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Mineral Wells | Amanda Shires | 4:11 | |
| Before the Night Is Gone | Zoe Muth and the Lost High Rollers | 5:47 | |
| Solving Problems | Brent Cobb | 2:34 | |
| Berlin | Gill Landry | 4:24 | |
| The Guitar Case | Amanda Anne Platt & the Honeycutters | 4:18 | |
| Weight of the World | Western Centuries | 3:22 | |
| Ain't the Man to Tell You So | Levi Parham | 3:02 | |
| Whiskey and Dandelions | Karen Jonas | 3:15 | |
| Can't Stop a Train | Ward Hayden & the Outliers | 3:16 | |
| Piedmont Sky | Caleb Caudle | 3:00 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| Sure Feels Good Anyway | Amy Ray | 4:30 | |
| Learning How to Live Alone | Travis Meadows | 4:06 | |
| There May Come a Day | Amanda Anne Platt & the Honeycutters | 3:18 | |
| Take Me for a Ride | Caitlin Canty | 4:09 | |
| Lookin' Back on Luckenbach | Whitney Rose | 4:17 | |