| Never A Forced Smile | Daniel Romano | 4:04 | |
| The Calm and the Crying Wind | Trampled by Turtles | 3:58 | |
| Hard Times | Gillian Welch | 4:52 | |
| Late September | Watchhouse | 4:20 | |
| Murmur of Yearning | Thomas Csorba | 3:50 | |
| The Moorings | Andrew Duhon | 3:26 | |
| Wrong Way to Run | Willy Tea Taylor | 2:34 | |
| Sorrow Be the Bird | Lula Wiles | 3:08 | |
| Thrift Store Dress | Jeffrey Martin | 3:29 | |
| American Poor | Dead Horses | 3:06 | |
| HoBo | Charlie Parr | 3:47 | |
| 120 East | The Brothers Comatose | 4:36 | |
| A Wanderer I'll Stay | Pharis & Jason Romero | 3:37 | |
| No Ordinary Blue | John Prine | 2:56 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Cairo, Il | The Brother Brothers | 3:42 | |
| 13 September | Daniel Steinbock | 3:36 | |
| Letters | Marty O'Reilly & the Old Soul Orchestra | 3:52 | |
| Million Dollar Bill | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:03 | |
| Up on the Mountaintop | The Deep Dark Woods | 3:25 | |
| Modern Man | Dead Horses | 3:01 | |
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| Rice Birds | Adam Carroll | 3:53 | |
| Backslide (OurVinyl Sessions) | Smooth Hound Smith, OurVinyl | 2:54 | |
| Angeline | Jeffrey Martin | 4:45 | |
| Too Stoned to Cry - 2019 Recut | Andrew Combs | 3:24 | |
| Like a Force of Nature | Todd Snider | 3:54 | |
| What Am I Living For | Cat Clyde, Jeremie Albino | 2:42 | |
| The Whole World Through | Jeffrey Martin | 4:29 | |
| Morning Bugle | Robert Ellis, Courtney Hartman | 3:00 | |
| When Will I Be Changed (feat. Bob Weir) | Josh Ritter, Bob Weir | 5:52 | |
| Railroad Man | The Stray Birds | 3:44 | |
| Where in the World Have You Been? | Dead Man Winter | 4:07 | |
| When It Breaks | Possessed by Paul James | 4:31 | |
| Dogs in the Daylight | Jeffrey Martin | 5:17 | |
| Nobody Gives a Damn About Songs Anymore | John Moreland | 3:15 | |
| All I Really Need to Know | Dead Horses | 4:15 | |
| Cold Canary Gaslight | Marty O'Reilly & the Old Soul Orchestra | 4:42 | |
| October Dark | Jeffrey Martin | 3:48 | |
| Cheap Wine | Charlie Parr | 5:11 | |
| Miss Ohio | Craig Cardiff | 4:25 | |
| Medicine for Living | Alexa Rose | 4:24 | |
| Chaos And Clothes | Jason Isbell and the 400 Unit | 3:34 | |
| Hold On | Redbird | 4:38 | |
| Sculptor (OurVinyl Sessions) | Jeffrey Martin, OurVinyl | 3:43 | |
| Sojourn of a Burning Sun | Daniel Rodriguez | 2:10 | |
| James Alley Blues | Willie Watson | 4:06 | |
| Joe | Max Gomez | 3:55 | |
| When We Could | Nathaniel Rateliff | 3:41 | |
| Milk And Honey | Ondara, Madison Cunningham | 2:54 | |
