| More and More, Less and Less | Delbert McClinton & Glen Clark | 2:53 | |
| True Love Travels on a Gravel Road | Nick Lowe | 3:36 | |
| Shake Sugaree | Rhiannon Giddens | 4:24 | |
| Deep Water | Amy Helm | 4:08 | |
| Lookin' Back on Luckenbach | Whitney Rose | 4:17 | |
| Oh Ireland | Chip Taylor, Carrie Rodriguez | 3:40 | |
| Funny 'Bout Love | Ray Bonneville | 3:44 | |
| Let Me Die in My Footsteps | Steep Canyon Rangers | 3:23 | |
| Trouble Me Anytime | Mary Bragg | 3:43 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Curves & Things | Chip Taylor, Carrie Rodriguez | 3:45 | |
| We Pave the Way | Orkesta Mendoza, Carrie Rodriguez | 3:37 | |
| Better to My Baby | Whitney Rose | 3:11 | |
| Wondering How | Pieta Brown | 3:06 | |
| Hearts Beat and Take a Beating | Forest Sun | 3:16 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Lonesome Whistle | Billy Bragg, Joe Henry | 2:53 | |
| Broken Man (Live) | Greg Trooper | 4:19 | |
| River Song | Tom Rush | 3:56 | |
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| Kiss Her Once for Me | Delbert McClinton | 4:01 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| People Get Old | Lori McKenna | 3:42 | |
| Weaker Moments | Chip Taylor, The New Ukrainians | 3:39 | |
| Sweet Dream | John Hiatt, Jerry Douglas | 4:28 | |
| Willow Tree | Diana Jones | 2:53 | |
| Willin' | Richard Shindell | 3:15 | |
| Where Have All the Flowers Gone | Eliza Gilkyson | 4:41 | |
| I've Just Seen a Face | Tami Neilson | 2:31 | |
| That's How I Feel | Dori Freeman | 2:43 | |
| I Can't Help It (if I'm Still in Love With You) | Chip Taylor, Carrie Rodriguez | 3:25 | |
| Oh It's You | Ray Bonneville | 4:48 | |
| Goin' Home | Malcolm Holcombe | 4:49 | |
| Down to Seeds and Stems Again | Bill Kirchen | 4:02 | |
| Espiritu Santo Bay | Kimmie Rhodes | 5:03 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| Memphis In My Mind | Whitney Rose | 2:53 | |
| Basil Gone to Blossom | Caitlin Canty | 3:07 | |
| It's Hard to Sing This Song | Chip Taylor | 4:09 | |
| The Sea & the Shore (feat. John Fullbright) | Amy Speace, John Fullbright | 4:14 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Long As I Can See The Light | Ted Hawkins | 3:13 | |
| Morning Is My Destination | Tift Merritt | 3:17 | |
| Alright Alright | Birds of Chicago | 4:02 | |
| I Can't Get You Off Of My Mind | Bob Dylan | 2:55 | |
| The Bramble And The Rose | Mary McCaslin, Jim Ringer | 3:18 | |
| Lay Down Your Weary Tune | Tim O'Brien | 3:28 | |