| Pack up Your Sorrows | Loudon Wainwright III, Iris DeMent | 2:44 | |
| Diamond Joe | Martin Simpson | 3:08 | |
| Youngstown | The Stairwell Sisters | 4:37 | |
| El Chaparral | Diana Jones | 3:18 | |
| Mercy | Po' Girl | 4:56 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Don't You Fall | The Be Good Tanyas | 3:38 | |
| High Atmosphere | Diana Jones | 2:44 | |
| Boneyard | The Honeycutters | 6:46 | |
| Northbound 35 | Richard Shindell | 5:18 | |
| Heart Like a Wheel | Zoe Muth and the Lost High Rollers | 3:37 | |
| Hymn for the Crossing | Amy Speace | 3:36 | |
| Come See About Me | Tom Rush | 2:50 | |
| Nobody in this World | The Honey Dewdrops | 4:15 | |
| Solitary Man | Tracy Grammer | 3:26 | |
| Working Man | Maya De Vitry | 3:22 | |
| The Coo Coo Bird | The Be Good Tanyas | 4:50 | |
| Tell Me A Story | Po' Girl | 3:13 | |
| Mama Don't Cry | I Draw Slow | 4:09 | |
| Lovin' Eyes | Applewood Road, Amber Rubarth, Amy Speace, Emily Barker | 2:15 | |
| Day After Tomorrow | Linda Thompson | 5:03 | |
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| Evangelina | Diana Jones | 3:11 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| Arroyo Seco | John Gorka | 4:24 | |
| It Makes No Difference | Shannon McNally | 5:27 | |
| The Late John Garfield Blues | Sara Watkins | 4:06 | |
| Hush, Sorrow | Buddy & Julie Miller, Buddy Miller, Julie Miller | 4:02 | |
| Catch the Wind | Kimmie Rhodes | 3:14 | |
| Not That Simple | The Honeycutters | 3:24 | |
| One Red Rose | Iris DeMent | 3:07 | |
| Hazel's House | Richard Shindell | 3:20 | |
| Morningside | John Gorka | 3:46 | |
| Houdini Didn't Like the Spiritualists (feat. Shannon McNally) | Terry Allen, The Panhandle Mystery Band, Shannon McNally | 4:04 | |
| Tell The Girls | I Draw Slow | 4:58 | |
| Ah, Me | Amelia Curran | 4:10 | |
| Willin' | Richard Shindell | 3:15 | |
| Disappearing Man | Dave Carter, Tracy Grammer | 3:49 | |
| Three Chords and Truth | Lynn Miles | 3:30 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Dark Eyed Gal (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:58 | |
| If You Want | Oliver Henley | 2:54 | |
| A Perfect World | Kate Campbell | 3:17 | |
| I Never | Caitlin Canty | 3:19 | |
| Two Gunslinger | Mirabelle Defoe | 3:27 | |
| Shades Of Gray | Cry Cry Cry | 5:05 | |
| Ain't No Ash Will Burn | Della Mae | 4:17 | |
| Song for a Worker | Diana Jones | 3:11 | |
| The West Was Burning | Martha Scanlan | 4:59 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
