| I'm Not Drunk I'm Just Drinking | Mack Allen Smith | 2:05 | |
| Silver and Gold | Trampled by Turtles | 2:47 | |
| Wayside / Back in Time | Gillian Welch | 3:28 | |
| All Blue | Luke Bell | 3:21 | |
| Goddamn Lonely Love - Remastered | Drive-By Truckers | 5:01 | |
| Big Cheeseburgers and Good French Fries | Blaze Foley | 3:23 | |
| The Way It Goes | Gillian Welch | 4:01 | |
| How Can I Miss You When You Won't Go Away | Dan Hicks & His Hot Licks | 2:39 | |
| Carmelita | Warren Zevon | 3:34 | |
| Katie | Fred Eaglesmith | 3:42 | |
| Luxury Liner | The International Submarine Band | 2:48 | |
| Saskatchewan in 1881 | Colter Wall | 2:51 | |
| Ain't Got a Place | James McMurtry | 2:41 | |
| Captain's Song (Sorley Boy) | The Orphan Brigade, John Prine | 3:11 | |
| Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone) | John Prine | 4:05 | |
| Waltz About Whiskey | Watchhouse | 3:46 | |
| Spanish Moon | Little Feat | 3:06 | |
| New Ways to Fail | Sarah Shook & the Disarmers | 4:07 | |
| Time Forgot (To Change My Heart) | Daniel Romano | 4:00 | |
| Please Let Me Go Round Again | Swamp Dogg, John Prine | 4:40 | |
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | |
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| Oklahoma Hills - Remastered | Arlo Guthrie | 3:27 | |
| Link Of Chain | Chris Smither | 4:50 | |
| Black Crow | Brent Cobb | 4:30 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Shanty | Jonathan Edwards | 2:35 | |
| Up on the Hill Where They Do the Boogie | John Hartford | 2:43 | |
| Far from Me | John Prine | 5:09 | |
| Squeezebox | Bruce Robison | 2:38 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Moonshiner | Uncle Tupelo | 4:23 | |
| You'll Get Yours Aplenty | Blaze Foley | 2:09 | |
| That's the Way That the World Goes 'Round | John Prine | 3:20 | |
| Accidentally Like a Martyr - 2007 Remaster | Warren Zevon | 3:42 | |
| I'm Just an Old Chunk of Coal (But I'm Gonna Be a Diamond Someday) | Billy Joe Shaver | 2:01 | |
| Keep It Clean | Willie Watson | 3:35 | |
| Roll Um Easy | Little Feat | 2:31 | |
| The "Ella B" - Remastered | Amazing Rhythm Aces | 4:33 | |
| Way Out West | Marty Stuart And His Fabulous Superlatives | 5:41 | |
| There She Goes | John Prine | 3:24 | |
| Anytime | Arlo Guthrie | 1:50 | |
| Barbeque | Robert Earl Keen | 4:41 | |
| Standing On The Rock | The Ozark Mountain Daredevils | 3:54 | |
| Mohawk River | Ramsay Midwood | 4:09 | |
| Always A Friend | Alejandro Escovedo | 3:35 | |
| If I Needed You | Townes Van Zandt | 3:44 | |
| The Road Goes On Forever | The Highwaymen | 4:41 | |
| Purple Rain | Dwight Yoakam | 4:42 | |
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | |