| Frozen Notes | Warren Zevon | 1:42 | |
| Angeline | James McMurtry | 4:04 | |
| Hello in There | John Prine | 4:32 | |
| World's Greatest Loser | Margo Price | 1:33 | |
| This Old Road | Marley's Ghost, John Prine | 3:57 | |
| Before the Night Is Gone | Zoe Muth and the Lost High Rollers | 5:47 | |
| If You Don't Want My Love | John Prine | 3:05 | |
| Roll Um Easy | Little Feat | 2:31 | |
| Oklahoma Hills - Remastered | Arlo Guthrie | 3:27 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Old Shoes | Tom Waits | 4:25 | |
| Needle & Thread | Eilen Jewell | 3:40 | |
| Kansas | Fred Eaglesmith | 3:44 | |
| If I've Only One Time Askin' | Daniel Romano | 2:54 | |
| After the Storm | The Flatlanders | 3:52 | |
| It's a Big Old Goofy World | John Prine | 5:10 | |
| Dreamsicle | Jason Isbell and the 400 Unit | 3:44 | |
| Captain's Song (Sorley Boy) | The Orphan Brigade, John Prine | 3:11 | |
| A Horse In The Country | Cowboy Junkies | 3:50 | |
| Childish Things | James McMurtry | 4:35 | |
| Goodnight Rhonda Lee | Nicole Atkins | 2:33 | |
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| Mystifies Me - 2015 Remaster | Son Volt | 4:12 | |
| Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone) | John Prine | 4:05 | |
| Hard Times In Babylon | Eliza Gilkyson | 4:05 | |
| Ain't Got a Place | James McMurtry | 2:41 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| She Is My Everything | John Prine | 4:25 | |
| The Whiskey Makes You Sweeter | Laura Cantrell | 5:07 | |
| Hobo's Lullaby | Arlo Guthrie | 3:57 | |
| Codeine | Jason Isbell and the 400 Unit | 5:44 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| If I Just Knew What to Say - Remastered | Amazing Rhythm Aces | 2:05 | |
| James Alley Blues | Willie Watson | 4:06 | |
| 'Cause Cheap Is How I Feel | Cowboy Junkies | 4:14 | |
| Me and Bobby McGee | Gordon Lightfoot | 3:46 | |
| Please Let Me Go Round Again | Swamp Dogg, John Prine | 4:40 | |
| Two Different Things | Caitlin Cary, Thad Cockrell | 4:16 | |
| Souvenirs | John Prine | 3:42 | |
| Missin' You | Little Feat | 2:21 | |
| Spookin' The Horses | Fred Eaglesmith | 4:07 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| Early Mornin' Rain | Gordon Lightfoot | 3:08 | |
| Drinking Too Much | Fred Eaglesmith | 3:55 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| White Line Fever | The Flying Burrito Brothers | 3:16 | |
| The Ballad Of Carol Lynn | Whiskeytown | 3:04 | |
| Between The Daylight And The Dark | Mary Gauthier | 4:15 | |