| Wichita | Gretchen Peters | 3:52 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Baby Doll | Malcolm Holcombe | 2:31 | |
| A Hard Rain's A-Gonna Fall | Eliza Gilkyson | 6:28 | |
| Road To Oblivion | Bow Thayer, Levon Helm | 4:17 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Let Me Die in My Footsteps | Steep Canyon Rangers | 3:23 | |
| Baby Can I Crawl Back To You | Gurf Morlix | 2:25 | |
| Trouble Is | Justin Townes Earle | 3:22 | |
| The Darker Side of Me | Otis Gibbs | 4:22 | |
| I'm The One Who Needs You Tonight | Cordovas | 2:48 | |
| A Hard Rain's Gonna Fall (feat. John Craigie & Ben Morrison) | Rainbow Girls, Ben Morrison, John Craigie | 6:21 | |
| Private Thoughts | Chip Taylor, Carrie Rodriguez | 4:01 | |
| No Not Me | Pieta Brown | 4:19 | |
| Pale Fire | Amanda Shires | 3:16 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Series of Closin' Doors | Gurf Morlix | 4:33 | |
| Standin' On The Porch | Cordovas | 2:42 | |
| Funny 'Bout Love | Ray Bonneville | 3:44 | |
| Brokedown Palace (Acoustic Version) | Shinyribs | 3:49 | |
| Everywhere Now | The Good Luck Thrift Store Outfit | 3:54 | |
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| Fear of Trains | William Elliott Whitmore | 4:00 | |
| Crashin' & Burnin' | Fred Eaglesmith | 3:44 | |
| Ain't Got a Place | James McMurtry | 2:41 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| The Sweet | Hackensaw Boys | 3:34 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| The Wind Doesn't Know You | Malcolm Holcombe | 2:42 | |
| Cool Cool Rain | Ray Bonneville | 3:46 | |
| Our Town | Iris DeMent | 5:00 | |
| Tell Me A Story | Po' Girl | 3:13 | |
| To A Scrapyard Bus Stop | Charlie Parr | 4:15 | |
| Love Will Win the War | Darden Smith | 3:54 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Torn and Wrinkled | Malcolm Holcombe, Iris DeMent | 3:15 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Rock and Roll Joe | Chip Taylor, Kendel Carson, John Platania | 4:04 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Who Carried You | Malcolm Holcombe | 3:27 | |
| Pallbearer | Josh Turner, Iris DeMent, Marty Stuart | 4:32 | |
| Deeper Well | David Olney | 3:07 | |
| It's Not Mine | Walter Gracie | 3:57 | |
| If I Can't Have You | Blackie & The Rodeo Kings, Lucinda Williams | 2:59 | |
| I Love It When She Lies | Greg Trooper | 3:32 | |
| Set Me Down On A Cloud | Lukas Nelson and Promise of the Real, Lucius | 7:16 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
| Fisherman's Friend | Ramsay Midwood | 4:58 | |