| Buddies | Lauren Barth | 3:25 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| Middle Child | Daniel Romano | 3:48 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | |
| Drag Queens In Limousines | Mary Gauthier | 5:39 | |
| Time Forgot (To Change My Heart) | Daniel Romano | 4:00 | |
| From Outer Space | Jaime Wyatt | 4:13 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| This Highway | Zephaniah OHora | 3:59 | |
| Old Mexico | Marty Stuart And His Fabulous Superlatives | 2:45 | |
| Please, Please, Please | Andrew Combs | 4:27 | |
| Fuck Up | Sarah Shook & the Disarmers | 3:21 | |
| It's All Over Now, Baby Blue | The Seldom Scene | 3:20 | |
| From What I Recall | Melissa Carper | 4:13 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| Sad Songs | Kassi Valazza | 4:06 | |
| Yum Yum | The Deslondes, Riley Downing, Dan Cutler, Sam Doores, Cameron Snyder | 2:56 | |
| Hold On I | Chris Smither | 4:03 | |
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| Got a Lotta Love | The Cactus Blossoms | 3:02 | |
| This Morning' I Was Born Again | Sam Doores, Riley Downing, The Tumbleweeds | 4:32 | |
| Stop the World and Let Me Off | John Doe, The Sadies | 3:42 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| This Changes Everything | Jim Lauderdale | 3:32 | |
| Travelers Paradise | The Cactus Blossoms | 2:58 | |
| Before the Night Is Gone | Zoe Muth and the Lost High Rollers | 5:47 | |
| Handyman | Esther Rose | 2:46 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Weakness | Margo Price | 2:47 | |
| End Of The End Of The World | Lee Ann Womack | 2:18 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Blue As the Ocean | The Cactus Blossoms | 3:21 | |
| Humidifier | Jonny Fritz | 2:22 | |
| Our Love Is Done | Hannah Juanita | 4:12 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| Lover's Lane | Micah P. Hinson | 3:02 | |
| June or September | Blaze Foley | 2:40 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
| Jealous Man | Hoyt Axton | 1:20 | |
| Hotel Amarillo | Caroline Spence | 4:00 | |
| You're Dreaming | The Cactus Blossoms | 3:23 | |
| Cold & Bitter Tears | Ted Hawkins | 2:14 | |
| Runnin’ Shine | Lukas Nelson and Promise of the Real | 3:22 | |
| Goodbye Old Missoula | Willis Alan Ramsey | 5:03 | |
| Key Chain | Slaid Cleaves | 3:15 | |
| No Place Like The Right Time | Donna The Buffalo | 4:22 | |
| Sweet Lucinda | Gibson Brothers | 2:45 | |
