| Wildwood | Chatham County Line | 3:06 | |
| Whim of Iron | Slaid Cleaves | 2:29 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Go on Home | Chris Knight | 3:20 | |
| You Got to Me | James McMurtry | 5:23 | |
| Border Radio | Kelly Willis, Bruce Robison | 2:50 | |
| Worth Dyin' For | Gurf Morlix | 4:42 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Green Mountains and Me | Slaid Cleaves | 4:23 | |
| Spittin’ On Fire | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:05 | |
| Morning Blues | Parker Millsap | 3:40 | |
| Leaving Louisiana in the Broad Daylight | Shovels & Rope | 3:33 | |
| Canola Fields | James McMurtry | 4:49 | |
| Omaha | The Gourds | 3:15 | |
| Clean Getaway | Kieran Kane, Kevin Welch, Fats Kaplin | 2:50 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Too Much Trouble | The Mallett Brothers Band | 5:24 | |
| Love Will Only Break Your Heart | The David Mayfield Parade | 2:53 | |
| If I Had a Rose | Bruce Robison, Kelly Willis | 3:20 | |
| She's a River | Gurf Morlix | 4:28 | |
| The Sweet | Hackensaw Boys | 3:34 | |
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| Hard to Believe | Slaid Cleaves | 3:41 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| I'll Be Loving You | The Honeycutters | 5:50 | |
| Lights of Cheyenne | James McMurtry | 6:40 | |
| Half-Broke Horse | Eilen Jewell | 3:26 | |
| Hush, Sorrow | Buddy & Julie Miller, Buddy Miller, Julie Miller | 4:02 | |
| Don't Look Back | Kasey Anderson | 6:04 | |
| Wishbones | Slaid Cleaves | 5:50 | |
| First Time in Years | Erik Koskinen | 3:52 | |
| Wrong Way to Run | Willy Tea Taylor | 2:34 | |
| Train to Birmingham | Kevin Welch | 4:13 | |
| Rock Salt and Nails | Willie Watson | 3:47 | |
| Great American Roadside | Otis Gibbs | 2:49 | |
| Weary Traveler | Three Tall Pines | 4:42 | |
| Just Us Kids | James McMurtry | 5:08 | |
| Hang Me in the Tulsa County Stars | John Moreland | 3:41 | |
| If I Had Known | Greg Brown | 3:25 | |
| Man I'm Supposed to Be | American Aquarium | 4:11 | |
| Porcelain Doll | Chatham County Line | 3:06 | |
| Winsome Smile | Chris Smither | 3:34 | |
| Alcohol And Pills | Fred Eaglesmith | 3:58 | |
| Time To Get A Gun | Fred Eaglesmith | 3:43 | |
| The Rock Of My Soul | Rodney Crowell | 4:50 | |
| Jacksonville Skyline | Whiskeytown | 3:00 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Seven Shells | Fred Eaglesmith | 2:23 | |
| Runnin’ Shine | Lukas Nelson and Promise of the Real | 3:22 | |
| The Rose of the San Joaquin | Tom Russell | 2:51 | |