| Ghosts of Our Fathers | Otis Gibbs | 3:46 | |
| Barbara's Song | Ian Noe | 3:25 | |
| California Blues | Alejandro Escovedo | 3:20 | |
| Song of the Bird | The Cactus Blossoms | 2:29 | |
| Rich Man's World | Eilen Jewell | 2:55 | |
| Railroad Bill | Billy Bragg, Joe Henry | 2:49 | |
| It Was a Train | Otis Gibbs | 3:10 | |
| Monkey And The Engineer | Dave Rawlings Machine | 3:38 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Lonesome Whistle | Billy Bragg, Joe Henry | 2:53 | |
| Hillbilly Blue (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:11 | |
| Ain't Waitin' | Justin Townes Earle | 2:16 | |
| Needle & Thread | Eilen Jewell | 3:40 | |
| All the Way to Amsterdam | Greg Trooper | 2:59 | |
| Isn't That So | Jesse Winchester | 2:25 | |
| Angeline | James McMurtry | 4:04 | |
| Five Hearts Breaking | Alejandro Escovedo | 4:10 | |
| Do Unto Others | Billy Bragg | 4:08 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Canola Fields | James McMurtry | 4:49 | |
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| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| St. Swithin's Day - Tom Robinson Now Playing 'Billy Bragg Takeover', 14th July 2019 | Billy Bragg | 2:53 | |
| Dead Skunk | Loudon Wainwright III | 3:05 | |
| Can't Hardly Wait | Justin Townes Earle | 2:48 | |
| Ford Econoline | Chuck Prophet | 3:41 | |
| Dwight Yoakam | Sarah Shook & the Disarmers | 3:40 | |
| The L&N Don't Stop Here Anymore | Billy Bragg, Joe Henry | 4:29 | |
| The Prettiest Thing | The Modern Don Juans, David Childers | 4:14 | |
| If I Could Only Catch My | Paul Burch, Billy Bragg, Jon Langford | 3:36 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Scare Me to Death | Joe Henry | 4:54 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Jesus Was a Social Drinker | Chuck Prophet | 4:54 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| Land of the Bottom Line | John Gorka | 3:33 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| Clean Getaway | Kieran Kane, Kevin Welch, Fats Kaplin | 2:50 | |
| In My Hour of Darkness - 2002 Remaster | Gram Parsons | 3:49 | |
| The Coo Coo Bird | Steve Martin, Edie Brickell | 3:19 | |
| Short Haired Woman Blues | Dave Rawlings Machine | 6:43 | |
| Tomorrow's Going to Be a Better Day | Billy Bragg | 3:10 | |
| Down Drinking at the Bar | Loudon Wainwright III | 3:57 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
| Long Black Veil - Remastered | The Band | 3:01 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |
| Wildflowers | Chris Hillman | 2:51 | |
| Blue | The Jayhawks | 3:09 | |