| You Got Gold | John Prine | 4:38 | |
| Texas Moon | Vincent Neil Emerson | 3:25 | |
| Ain't Glad I'm Leaving | Justin Townes Earle | 2:32 | |
| No Love Today | Chris Smither | 4:44 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| Rock Bottom, Pop. 1 | Robbie Fulks | 2:40 | |
| Nothing Wrong with Texas | Sunny Sweeney | 3:19 | |
| What's She Crying For | Justin Townes Earle | 3:53 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Your Lonely Heart | Carrie Rodriguez | 2:58 | |
| Picture Show | John Prine | 3:22 | |
| My Sweet Annette | Drive-By Truckers | 3:51 | |
| You Cared Enough to Lie | Eilen Jewell | 2:47 | |
| Cold, Cold World | Blaze Foley | 3:23 | |
| Love’s Gonna Live Here | Buddy Miller, Kacey Musgraves | 2:14 | |
| Run-down Neighborhood | Lindi Ortega | 3:06 | |
| Cold, Cold Heart (feat. Miranda Lambert) | John Prine, Miranda Lambert | 3:32 | |
| Barbara's Song | Ian Noe | 3:25 | |
| No More Crying The Blues | The Cactus Blossoms | 2:03 | |
| Dead Skunk | Loudon Wainwright III | 3:05 | |
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| The Darker Side of Me | Otis Gibbs | 4:22 | |
| Kansas | Fred Eaglesmith | 3:44 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| Changed the Locks | Lucinda Williams | 3:43 | |
| The Prettiest Thing | The Modern Don Juans, David Childers | 4:14 | |
| Straightjacket Love | Elizabeth Cook | 2:46 | |
| Angel from Montgomery - 2008 Remaster | Bonnie Raitt | 3:59 | |
| Half-Broke Horse | Eilen Jewell | 3:26 | |
| Give It Away | The Trishas | 3:16 | |
| Oh, Tonight (feat. Kacey Musgraves) | Josh Abbott Band, Kacey Musgraves | 3:25 | |
| Texas Love Song | Slaid Cleaves | 3:03 | |
| Whole Lotta Highway (With A Million Miles to Go) | Marty Stuart And His Fabulous Superlatives | 3:18 | |
| Trucker's Funeral | Whitney Rose | 4:55 | |
| Stone Hotel | Jaime Wyatt | 4:02 | |
| Mental Cruelty (feat. Kacey Musgraves) | John Prine, Kacey Musgraves | 2:23 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Killing the Blues | Chris Smither | 5:49 | |
| Dreamsicle | Jason Isbell and the 400 Unit | 3:44 | |
| If Wishes Were Horses | Claire Lynch | 2:36 | |
| El Paso | Tom Russell | 5:38 | |
| Broke Down | Slaid Cleaves | 3:10 | |
| Can't Let Go | Lucinda Williams | 3:28 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| Valley Road | James McMurtry | 4:45 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Drunken Angel | Lucinda Williams | 3:20 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| I'm Still Here | John Hartford | 3:24 | |