| Union Pacific | The Wooks | 2:53 | ||
| Sometimes Wine | Sturgill Simpson | 3:55 | ||
| 50 Dollars a Week | South Texas Tweek | 3:24 | ||
| Daddy's Cup | Drive-By Truckers | 5:53 | ||
| Mama's Don't Let Your Cowboys Grow Up to be Babies | Dale Watson | 3:25 | ||
| Let's All Help the Cowboys (Sing the Blues) | Colter Wall | 3:04 | ||
| All American Singer | Zephaniah OHora | 3:57 | ||
| Don't Wanna Cry | Emily Nenni | 2:26 | ||
| Sometimes Dogs Bark at Nothing | JP Harris | 2:27 | ||
| Prairie Funeral | Brennen Leigh | 3:04 | ||
| Mexican Cowboy | Willie Watson | 3:53 | ||
| I Don't Believe | Jeremy Pinnell | 3:04 | ||
| Someday, Not Today | The Broken Spokes | 2:28 | ||
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | ||
| Highway Shine | Vincent Neil Emerson | 3:33 | ||
| Own Private Honky Tonk | Western Centuries | 3:39 | ||
| All Blue | Luke Bell | 3:21 | ||
| Songs My Mama Sang | Zephaniah OHora | 3:07 | ||
| Ol' Dood (Part I) | Sturgill Simpson | 2:57 | ||
| The Highway 16 Shuffle | Garrett T. Capps | 3:41 | ||
| Still Someone | The Deslondes, Riley Downing | 3:07 | ||
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| If This Is Just a Game | Emily Nenni | 3:44 | ||
| Vanlife | Willi Carlisle | 4:46 | ||
| On The Road Again (feat. The Fairfield Four) | Willie Watson, The Fairfield Four | 2:27 | ||
| Holy Dirt | John R. Miller | 2:57 | ||
| All the Pretty Colors | Sturgill Simpson | 2:18 | ||
| Errol's Song | Adam Carroll | 4:36 | ||
| Must Be the Whiskey | Josh Morningstar | 3:30 | ||
| Katie | Fred Eaglesmith | 3:42 | ||
| Let's Have A Good Thing Together | Jim Lauderdale | 2:09 | ||
| I'm Alright With This | Jeremy Pinnell | 3:59 | ||
| Country Morning Music | Keith Sykes | 2:27 | ||
| The Highway Less Taken | Justin Wells | 3:22 | ||
| Night Time Eagle | Jeremy Pinnell | 3:04 | ||
| I Ain't Drunk | Whitey Morgan and the 78's | 3:00 | ||
| Miss'ippi | Nick Shoulders | 3:23 | ||
| Bloodshot Heart | Pat Reedy | 3:30 | ||
| Sitting Here Without You | Sturgill Simpson | 2:10 | ||
| You're the Reason Our Kids Are Ugly (feat. Nikki Lane) | JP Harris, Nikki Lane | 2:34 | ||
| I Do Believe I've Had Enough | Zephaniah OHora | 3:44 | ||
| Silver and Gold | Trampled by Turtles | 2:47 | ||
| Down in My Hometown | The Flatlanders | 2:45 | ||
| Just A Heart | James Hand | 3:27 | ||
| River Of Fools | Logan Ledger | 3:11 | ||
| The Truth Will Set You Free | James Hand | 2:15 | ||
| Borrowed Time | John R. Miller | 5:02 | ||
| Alcohol And Pills | Fred Eaglesmith | 3:58 | ||
| Mississippi Flush | Ray Wylie Hubbard | 3:33 | ||
| The Lights Of San Francisco | Logan Ledger | 5:01 | ||
