| You Don't Scare Me | Whitney Rose | 4:10 | |
| Giving up on Your Hometown | Lori McKenna | 3:15 | |
| Too Bad | Lilly Hiatt | 3:11 | |
| Oyster and Pearl | Amy Ray, Phil Cook, Brad Cook, Justin Vernon | 4:00 | |
| Debtors' Prison | Dustbowl Revival | 4:53 | |
| Child of the Wind | Michaela Anne | 3:20 | |
| Before the Night Is Gone | Zoe Muth and the Lost High Rollers | 5:47 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Golden Child | The Honeycutters | 3:34 | |
| Sure Feels Good Anyway | Amy Ray | 4:30 | |
| My Name Can't Be Mama | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires | 2:30 | |
| Hawk For The Dove | Amanda Shires | 3:47 | |
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | |
| River Alone | Caitlin Canty | 4:54 | |
| Time to Give | Sera Cahoone | 2:34 | |
| Please, Please, Please | Andrew Combs | 4:27 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Man I'm Supposed to Be | American Aquarium | 4:11 | |
| Grave Angels | Joe Henry | 5:31 | |
| I'll Be Loving You | The Honeycutters | 5:50 | |
| Trouble Me Anytime | Mary Bragg | 3:43 | |
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| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Eve's Daughter | Amanda Shires | 3:10 | |
| Highwomen | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires, Yola | 3:32 | |
| Only Always | Nicki Bluhm and the Gramblers | 3:19 | |
| Unmistakable Love | Spencer Burton | 3:55 | |
| Goddamn Lonely Love - Remastered | Drive-By Truckers | 5:01 | |
| Take It from Me | Andrew Combs | 4:17 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Another Day | Ordinary Elephant | 4:55 | |
| Hey Stranger | Watchhouse | 3:27 | |
| Call Me Sometime | Becky Warren | 3:24 | |
| People Get Old | Lori McKenna | 3:42 | |
| Devil's Got My Woman | Andrew Combs | 2:35 | |
| Still a Child | Dori Freeman | 3:41 | |
| Different Kind Of Gone | Mary Gauthier | 3:41 | |
| No Glory in Regret | John Moreland | 4:56 | |
| Love Will Only Break Your Heart | The David Mayfield Parade | 2:53 | |
| Kentucky, 1988 | Kelsey Waldon | 4:04 | |
| White Gardenias | Justin Townes Earle | 2:38 | |
| Mineral Wells | Amanda Shires | 4:11 | |
| You Won't Find Me | Amelia Curran | 3:23 | |
| Carry Me | The Secret Sisters | 4:05 | |
| Half-Broke Horse | Eilen Jewell | 3:26 | |
| All Kinds Of People | Lilly Hiatt | 2:39 | |
| White Girl | The Milk Carton Kids | 3:44 | |
| Nashville 1972 | Rodney Crowell | 3:53 | |
| Hush, Sorrow | Buddy & Julie Miller, Buddy Miller, Julie Miller | 4:02 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |