| Thinkin' On You | Courtney Marie Andrews | 3:09 | |
| Time Stands Still | Chris Smither | 3:45 | |
| Birthday Song | Amanda Anne Platt & the Honeycutters | 4:15 | |
| Fear of Trains | William Elliott Whitmore | 4:00 | |
| Joke’s On Me | Rachel Baiman | 2:46 | |
| Calling for You | Iris DeMent | 3:18 | |
| Canyoneers | Jake Xerxes Fussell | 4:33 | |
| I Won't Let It | Daniel Romano | 4:08 | |
| Speed of the Sound of Loneliness | Nanci Griffith | 4:20 | |
| Barbed Wire (Belly Crawl) | Margo Cilker | 2:44 | |
| I'll Be Yours | The Americans | 5:47 | |
| These Are The Good Old Days | Courtney Marie Andrews | 2:35 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| Thinkin' on You | Rachel Baiman | 4:19 | |
| Plastic Bouquet | Kacy & Clayton, Marlon Williams | 2:57 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Traveling | Dawn Landes | 3:15 | |
| Tehachapi | Margo Cilker | 3:07 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| A Petal Here, a Petal There | Dead Horses | 3:26 | |
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| Just Like Tom Thumb's Blues | The Handsome Family | 5:39 | |
| Please, Please, Please | Andrew Combs | 4:27 | |
| Freedom | Rose Cousins | 4:28 | |
| Fall City | Courtney Marie Andrews | 4:33 | |
| My Love for You Will Not Fade | Caitlin Canty | 3:52 | |
| Maria | I Draw Slow | 3:07 | |
| Devil's Got My Woman | Andrew Combs | 2:35 | |
| Wreck You | Lori McKenna | 3:18 | |
| If It Rains | Basia Bulat | 2:33 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| Coming Down For You | Joan Shelley | 3:12 | |
| Too Stoned to Cry - 2019 Recut | Andrew Combs | 3:24 | |
| Santa Fe | Samantha Crain | 4:21 | |
| Ships in the Night | Courtney Marie Andrews | 4:02 | |
| A Hold On Me | Diana Jones | 4:20 | |
| Pale Moon | Shannon McNally, Neal Casal | 4:39 | |
| Forever and Then Some | Lillie Mae | 4:49 | |
| Only Lies | Robert Ellis | 3:50 | |
| Go And Leave Me | Kacy & Clayton | 3:34 | |
| The Woman You Are | Gill Landry | 5:12 | |
| Better to My Baby | Whitney Rose | 3:11 | |
| 2 Dollar Shoes | Rosie Thomas | 3:10 | |
| Tennessee River Runs Low | The Secret Sisters | 3:41 | |
| No One Has the Answers | Holly Macve | 3:28 | |
| 18th Of December | The Deep Dark Woods | 3:49 | |
| The Ballad Of Minnie Dean | Delaney Davidson, Marlon Williams | 2:48 | |
| Hold Steady / Rock Slow | Birds of Chicago | 5:15 | |
| Headlight | Della Mae | 3:54 | |