| Jenny of the Roses | Hiss Golden Messenger | 3:38 | |
| American Tune | Willie Nelson | 4:20 | |
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | |
| Fountain of Sorrow - 2014 Remaster | Jackson Browne | 6:52 | |
| Pick Up the Tempo | Waylon Jennings | 2:34 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| Beauty Way | Eliza Gilkyson | 3:02 | |
| When a Woman Goes Cold | Mary Gauthier | 3:51 | |
| Thoughts and Prayers | Drive-By Truckers | 5:21 | |
| The Watchman's Gone | Gordon Lightfoot | 4:18 | |
| Roll Um Easy | Little Feat | 2:31 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| When Will I Be Changed (feat. Bob Weir) | Josh Ritter, Bob Weir | 5:52 | |
| The Whole Night Sky | Bruce Cockburn | 3:54 | |
| Energy Follows Thought | Willie Nelson | 3:17 | |
| Colfax Avenue | The Delines | 3:30 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Once They Banned Imagine | Drive-By Truckers | 4:11 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| My Favorite Picture of You | Willie Nelson | 3:55 | |
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| Darkest Hour | Bob Weir | 3:24 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| Ghost Repeater | Jeffrey Foucault | 5:10 | |
| Thunderbird | John Hiatt | 4:04 | |
| Irish Girl | Mike Campbell & The Dirty Knobs | 4:25 | |
| I'm The One Who Needs You Tonight | Cordovas | 2:48 | |
| Lonesome Whistle | Billy Bragg, Joe Henry | 2:53 | |
| Guns of Umpqua | Drive-By Truckers | 3:51 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| Ballad of Easy Rider | The Byrds | 2:04 | |
| Long May You Run - 2017 Remaster | The Stills-Young Band | 3:48 | |
| Broken Arrow | Robbie Robertson | 5:23 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| Songbird | Willie Nelson | 2:39 | |
| Fun For Awhile | Peter Wolf | 3:35 | |
| The Night They Drove Old Dixie Down | The Band | 3:31 | |
| A Feather's Not A Bird | Rosanne Cash | 3:18 | |
| To Be Without You | Ryan Adams | 3:21 | |
| Let Your Loss Be Your Lesson | Robert Plant, Alison Krauss | 4:01 | |
| I Just Can't Let You Say Good-Bye | Willie Nelson | 4:38 | |
| Gone Gone Gone (Done Moved On) | Robert Plant, Alison Krauss | 3:32 | |
| Tell Moses | Colvin & Earle | 3:41 | |
| Hockey Skates | Kathleen Edwards | 4:28 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| The Banks of the Leopold Canal | The Deep Dark Woods | 6:08 | |
| Somebody Pick Up My Pieces | Willie Nelson | 4:39 | |
| A Kiss Before I Go | Ryan Adams & The Cardinals | 2:04 | |
| Night Life | B.B. King, Willie Nelson | 4:32 | |