| Wasting My Time | Zoe Muth | 3:55 | |
| Knights Ferry | Willy Tea Taylor, The Fellership, The Bait and Tackle Choir Oregon Chapter | 4:01 | |
| Voices | Jam in the Van, Joshua Ray Walker | 4:13 | |
| Knock-Kneed Ballerina | The Kernal | 3:12 | |
| How I Got To Memphis | The V-Roys | 4:38 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| Rodeo | Jeremy Pinnell | 3:10 | |
| Blood Is Thicker Than Water | Shaver | 3:27 | |
| What's She Crying For | Justin Townes Earle | 3:53 | |
| When The Wheels Touch Down | Wrinkle Neck Mules | 4:11 | |
| Nancy Barnett | Otis Gibbs | 3:27 | |
| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | |
| Song for Ian Tyson | Old Man Luedecke | 3:28 | |
| The Wheel | John R. Miller | 3:05 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Against the Skyline (feat. Kevin Welch) | Craig Moreau, Kevin Welch | 5:18 | |
| Dopamine Dream | Wrinkle Neck Mules | 3:50 | |
| Down to Seeds and Stems Again | Bill Kirchen | 4:02 | |
| Wilder Than Her | Fred Eaglesmith | 4:54 | |
| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| Sleep Song | Jeremy Pinnell | 3:14 | |
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| Back to Jackson | Jason Eady & The Wayward Apostles | 4:12 | |
| Wrong Time to Be Right | Sam Doores, Riley Downing, The Tumbleweeds | 4:35 | |
| Borderless Love | The Flatlanders | 3:16 | |
| Two for the Road | JP Harris | 2:54 | |
| Willin' | Richard Shindell | 3:15 | |
| Detroit Steel | Otis Gibbs | 2:50 | |
| If Today Doesn't Do Me In | Ian Noe | 3:57 | |
| Girl from the North Country | Kinky Friedman | 2:49 | |
| Pay No Attention to Alice | Patterson Hood | 3:11 | |
| Hard to Trust | Friedrich Buhler | 2:03 | |
| Bernadine (feat. Chris Carroll) | Adam Carroll, Chris Carroll | 4:31 | |
| Nobody Gives a Damn About Songs Anymore | John Moreland | 3:15 | |
| The Way We Are | The Flatlanders | 3:12 | |
| When the Waters Were One | Joseph Huber | 4:19 | |
| You Found Me | Willy Tea Taylor | 3:20 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Hallelujah Shine | The Gourds | 3:36 | |
| It's Been A Long Time | Fred Eaglesmith | 2:52 | |
| Blow Me a Kiss | Blackie & The Rodeo Kings | 3:12 | |
| Warm Guns | Western Centuries | 4:55 | |
| Outlaw Life | Jeremy Pinnell | 3:43 | |
| Indianapolis | The Bottle Rockets | 3:32 | |
| Jesus Christ With Signs Following | The Gourds | 4:06 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Twelve Men Dead In Sago | Otis Gibbs | 2:38 | |
| A Young Felon Dates an Old Woman | Ian Noe | 3:14 | |
| Hired Hand | Gail Steiger | 2:59 | |
| The Handbook | The Honeycutters | 3:04 | |