| Rich Man's World | Eilen Jewell | 2:55 | |
| Hang Me, Oh Hang Me | The Deep Dark Woods | 4:22 | |
| How Many Women | Lydia Loveless | 3:44 | |
| Man of God | Eliza Gilkyson | 4:27 | |
| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| Dusty Old Man | Tift Merritt | 3:47 | |
| Honky Tonks and Taverns | Lillie Mae | 2:19 | |
| I'll Trade You Money for Wine | Robbie Fulks | 4:33 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| I Love The Way | Yarn | 3:08 | |
| River Girl | Kelley Mickwee | 4:47 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Walking Proof | Lilly Hiatt | 3:55 | |
| Tecumseh Valley | Nanci Griffith | 4:29 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Black Haired Boy | Shannon McNally | 3:13 | |
| Somebody I Know | Zoe Muth | 5:09 | |
| Most In The Summertime | Rhett Miller, Black Prairie | 4:47 | |
| I Follow Rivers | Jason Isbell, Amanda Shires | 2:37 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
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| To Love Somebody | Lydia Loveless | 4:38 | |
| Loose Change | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires | 2:22 | |
| High in Heels | Kelsey Waldon | 3:40 | |
| Crocodile Man | Dave Carter, Tracy Grammer | 3:02 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Deer Creek Canyon | Sera Cahoone | 3:18 | |
| Paper Gown | Caroline Herring | 4:31 | |
| Three Chords and Truth | Lynn Miles | 3:30 | |
| Brightest Star | Lilly Hiatt | 3:07 | |
| Lay My Burden Down | Aoife O'Donovan | 3:36 | |
| You Found Me | Willy Tea Taylor | 3:20 | |
| Mirror, Mirror | Amanda Shires | 2:47 | |
| Cocktail And A Song | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires | 3:37 | |
| Here In the Going Going Gone | Greg Brown | 3:49 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| You Say | Dori Freeman | 2:54 | |
| Hands on a Grain of Sand | Amelia Curran | 3:48 | |
| The Last Bus | Zoe Muth | 5:59 | |
| Table For One | Courtney Marie Andrews | 3:59 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| Two Time Loser | The Deep Dark Woods | 4:27 | |
| You Won't Find Me | Amelia Curran | 3:23 | |
| The Guitar Case | Amanda Anne Platt & the Honeycutters | 4:18 | |
| Let There Be Lonely | The Secret Sisters | 3:09 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Everything I Do | Whiskeytown | 4:31 | |
| Hockey Skates | Kathleen Edwards | 4:28 | |