| Lonely Are the Free | Steve Earle | 3:23 | ||
| Time Stands Still | Chris Smither | 3:45 | ||
| Tinker Creek | Barna Howard | 4:06 | ||
| The Woman You Are | Gill Landry | 5:12 | ||
| Heart Like a Wheel | Zoe Muth and the Lost High Rollers | 3:37 | ||
| Dawned On Me | Jeff Tweedy | 2:52 | ||
| Clip Your Wings | The Dead Tongues | 3:13 | ||
| Cool Criminal | The Cave Singers | 4:19 | ||
| When We Fall | Phosphorescent | 3:29 | ||
| I Hear Them All | Dave Rawlings Machine | 2:27 | ||
| Irene | Courtney Marie Andrews | 3:46 | ||
| Nation of Heat | Joe Pug | 4:19 | ||
| Delta Momma Blues | Hurray For The Riff Raff | 3:48 | ||
| Wicked Spell | Rachel Baiman | 6:31 | ||
| Dogwood | Terry Allen | 4:31 | ||
| White Girl | The Milk Carton Kids | 3:44 | ||
| Tupelo Child | Phil Cook | 3:34 | ||
| Old Shoes | Tom Waits | 4:25 | ||
| Madman | Sean Rowe | 3:59 | ||
| Roll Julia | The Deep Dark Woods | 3:03 | ||
| What Are They Doing In Heaven Today? | The Deslondes, Sam Doores, Twain | 3:00 | ||
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| Wrong Time to Be Right | Sam Doores, Riley Downing, The Tumbleweeds | 4:35 | ||
| Say Grace | Sam Baker | 4:19 | ||
| Brunswick Stew | Kacy & Clayton | 3:10 | ||
| Stadium Inn | Jonny Fritz | 2:44 | ||
| Not Over By Half | Joan Shelley | 4:33 | ||
| Tour Song | Robert Ellis | 7:15 | ||
| Aerosol Ball | The Felice Brothers | 3:50 | ||
| The Trip | Dave Rawlings Machine | 10:55 | ||
| Horizons Fade | Barna Howard | 4:07 | ||
| Dear Mexico (Thank You for Joyce) | Twain | 4:05 | ||
| What Good | Tré Burt | 3:22 | ||
| The Longest Day | Megafaun | 3:51 | ||
| Winner's Casino | Richmond Fontaine | 4:06 | ||
| TV Song | Robert Ellis | 4:46 | ||
| Strange Country | Kacy & Clayton | 3:32 | ||
| Blue and Wonder | Richard Buckner | 3:47 | ||
| Lindsey Button | David Rawlings | 5:03 | ||
| Spanish Moss | Jackson C. Frank | 4:30 | ||
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | ||
| Million Dollar Bill | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:03 | ||
| Broken Cowboy | Jesse Woods | 2:20 | ||
| I Don't Fall Much, Anymore | Barna Howard | 3:44 | ||
| Flowers of Love | Pieta Brown, Justin Vernon | 3:27 | ||
| Buckets of Rain | Redbird | 3:41 | ||
| Who Carried You | Malcolm Holcombe | 3:31 | ||
| My Old Record | Delaney Davidson, Marlon Williams | 5:08 | ||
| The Maker | Willie Nelson | 5:08 | ||
| Hoping Machine | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 4:52 | ||
