| Borderline | Eliza Gilkyson | 2:42 | |
| A Hold On Me | Diana Jones | 4:20 | |
| Midnight on the Water | Caroline Herring | 4:04 | |
| Thinkin' on You | Rachel Baiman | 4:19 | |
| Tom's Gone to Hilo | Gavin Friday, Shannon McNally | 4:50 | |
| Every Time You Leave | Shelby Lynne, Allison Moorer | 2:23 | |
| Carolina in the Pines (with Indigo Girls) | Alison Brown, Indigo Girls | 4:57 | |
| Alice | Jamie Lin Wilson | 3:17 | |
| Maiden Voyage | Caroline Herring | 3:41 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| I Know What It's Like | Amanda Shires | 4:38 | |
| A Change Is Gonna Come | Shannon McNally | 3:16 | |
| You Won't Find Me | Amelia Curran | 3:23 | |
| Still a Child | Dori Freeman | 3:41 | |
| All That's Left Is Fare-Thee-Well (feat. Charlie Sexton) | Terry Allen, The Panhandle Mystery Band, Charlie Sexton | 3:06 | |
| Let's Just Be Friends for Tonight | Zoe Muth and the Lost High Rollers | 3:46 | |
| When You're Gone | Amanda Shires | 3:06 | |
| My Beloved | Diana Jones | 3:29 | |
| East Virginia Blues | Robert Earl Keen | 3:34 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| It's Never Too Late to Call | Paul Thorn | 3:01 | |
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| Nothing Good Can Come from This | Amy Speace | 3:11 | |
| Romeo's Tune | Nicki Bluhm | 3:53 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| Sooner or Later | Eliza Gilkyson | 4:21 | |
| Ricochet | Pieta Brown | 2:49 | |
| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| Heart Like a Wheel | Zoe Muth and the Lost High Rollers | 3:37 | |
| The Garage | Caleb Caudle | 2:33 | |
| Miles Away | Roseanne Reid | 2:24 | |
| Willow Tree | Diana Jones | 2:53 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
| Tattered, Torn and Blue (And Crazy) | Michaela Anne | 3:20 | |
| Train to Birmingham | Kevin Welch | 4:13 | |
| Wild Roses | Kimmie Rhodes | 3:06 | |
| No Rust on My Spade | Otis Gibbs | 4:17 | |
| Somebody I Know | Zoe Muth | 5:09 | |
| Devil's Got My Woman | Andrew Combs | 2:35 | |
| Tonight I'm Paying the Rent | Amy Ray | 4:17 | |
| Death in Arkansas | Eliza Gilkyson | 4:18 | |
| I Don't Think About You at All | Lauren Morrow | 4:22 | |
| The Stuff You Gotta Watch | Shannon McNally | 2:40 | |
| Child of the Wind | Michaela Anne | 3:20 | |
| The Messenger | Ray Wylie Hubbard, Ronnie Dunn, Pam Tillis | 4:33 | |
| The Hard Way | Shannon McNally | 4:27 | |
| Alright Alright | Birds of Chicago | 4:02 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Rabbit Hole | Rosanne Cash, Colin Meloy | 4:07 | |