| Sin in Indiana | Scott Miller & The Commonwealth | 2:12 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| The Old You | Western Centuries | 3:09 | |
| I Hope I Die (feat. Michael Rose) | Parker Millsap, Michael Rose | 2:59 | |
| Pickin' Time | Kinky Friedman | 1:41 | |
| Nobody Gives a Damn About Songs Anymore | John Moreland | 3:15 | |
| Pilgrim's Progress | Kris Kristofferson | 2:14 | |
| Run Johnny Run | William Elliott Whitmore | 2:28 | |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| Prairie Funeral | Brennen Leigh | 3:04 | |
| In My Cups | Western Centuries | 3:02 | |
| Shadow of the Moon | The Flatlanders | 2:52 | |
| Road Less Traveled | Yarn | 2:58 | |
| Big Cheeseburgers and Good French Fries | Gurf Morlix | 2:51 | |
| By the Waters of the James | The Local Honeys | 5:10 | |
| Parking Lots | John R. Miller | 3:35 | |
| Paid My Dues (feat. Jack Ingram) | Bruce Robison, Jack Ingram | 3:22 | |
| Wilder Than Her - Live at Corner Hotel, Melbourne, Australia | Audrey Auld, Fred Eaglesmith | 5:04 | |
| Make a New Start | Jason Dea West | 4:35 | |
| Home Is Where The Hurt Is | JP Harris | 3:10 | |
| Bull Riders & Songwriters | Willy Tea Taylor | 5:15 | |
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| Son of the Working Class | Josh Okeefe | 2:56 | |
| I Love You, Charlene | The Local Honeys | 2:54 | |
| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| Jenny Smith | Fred Eaglesmith | 4:11 | |
| Five Feet High and Rising | William Elliott Whitmore | 2:19 | |
| Strung Out | John R. Miller | 4:34 | |
| Barbara's Song | Ian Noe | 3:25 | |
| Never Go Home | Jason Dea West | 4:35 | |
| The Darker Side of Me | Otis Gibbs | 4:22 | |
| Keep It Clean | Willie Watson | 3:35 | |
| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | |
| Truckstop Amphetamines | JP Harris | 2:38 | |
| Twelve Men Dead In Sago | Otis Gibbs | 2:38 | |
| The Buck Starts Here | Robbie Fulks | 3:44 | |
| The Old General Store Is Burning Down | The Tillers | 4:21 | |
| Tin Pot Nelly | Fred Eaglesmith | 2:11 | |
| Jackson | Josh Okeefe, Cora Carpenter | 2:35 | |
| Story of You | The Flatlanders | 2:00 | |
| When The Wheels Touch Down | Wrinkle Neck Mules | 4:11 | |
| I Only Drink Alone | JP Harris | 2:30 | |
| Freedom to Stay | Kinky Friedman | 2:57 | |
| Silver Lining | Carl Anderson | 2:30 | |
| Half-Broke Horse | Eilen Jewell | 3:26 | |
| Free Little Bird | Willi Carlisle | 1:48 | |
| Down in the Woods | Malcolm Holcombe | 3:24 | |
| The John Deere H | Brennen Leigh | 3:15 | |
| Spookin' The Horses | Fred Eaglesmith | 4:07 | |
| Who Carried You | Malcolm Holcombe | 3:31 | |
