| Sadder Day | Western Centuries | 4:30 | ||
| Nobody Gives a Damn About Songs Anymore | John Moreland | 3:15 | ||
| Paid My Dues (feat. Jack Ingram) | Bruce Robison, Jack Ingram | 3:22 | ||
| Midnight Special | Willie Watson | 4:38 | ||
| Down in My Hometown | The Flatlanders | 2:45 | ||
| Childish Things | James McMurtry | 4:35 | ||
| I Ain't Lookin' for No Trouble | Ray Benson | 4:02 | ||
| Whistlers & Sparklers | Wrinkle Neck Mules | 3:48 | ||
| I Backslide on Friday | Paul Thorn | 3:34 | ||
| Cosmic Cowboy | Michael Martin Murphey, Willie Nelson, Jerry Jeff Walker, Lyle Lovett, Bruce Robison, Django Walker, Gary P. Nunn, Bob Livingston | 4:16 | ||
| Irene | Ian Noe | 3:53 | ||
| Train Home | Chris Smither | 4:25 | ||
| 25 Years | Yarn | 4:02 | ||
| Bubble Gum | Adam Carroll | 3:34 | ||
| Magnolia | The Gourds | 2:50 | ||
| James Alley Blues | Willie Watson | 4:06 | ||
| I Have A Good Day | Paul Thorn | 3:14 | ||
| Ionlanthe | James McMurtry | 4:30 | ||
| Don't Look for Me | Jeffrey Foucault | 3:05 | ||
| Home Is Where The Hurt Is | JP Harris | 3:10 | ||
| Hard to Be an Outlaw (feat. Willie Nelson) | Billy Joe Shaver, Willie Nelson | 3:06 | ||
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| These Things I've Come to Know | James McMurtry | 3:18 | ||
| Rock Salt and Nails | Willie Watson | 3:47 | ||
| Sometimes Dogs Bark at Nothing | JP Harris | 2:27 | ||
| Johnny Cash | Fred Eaglesmith | 3:20 | ||
| Pill Bug Blues | The Gourds | 3:59 | ||
| Highway Shine | Vincent Neil Emerson | 3:33 | ||
| 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 | ||
| Dear Mama, I'm So Sorry | Yarn | 2:50 | ||
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | ||
| Tuscaloosa 1962 | Donnie Fritts | 3:22 | ||
| Just Us Kids | James McMurtry | 5:08 | ||
| Only the Song Survives | John Hiatt | 4:00 | ||
| Blue Canoe | Blue Mountain | 4:39 | ||
| Dog | The Bottle Rockets | 2:20 | ||
| Errol's Song | Adam Carroll | 4:36 | ||
| Mayfly | Jeffrey Foucault | 3:34 | ||
| Katie | Fred Eaglesmith | 3:42 | ||
| Wild Birds | Western Centuries | 4:25 | ||
| Watch Me Fall | Uncle Tupelo | 2:12 | ||
| Satin Sheets | Willis Alan Ramsey | 2:39 | ||
| Ramblin', Scramblin' | Jerry Jeff Walker | 4:23 | ||
| Wide River To Cross | Levon Helm | 4:51 | ||
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | ||
| The Blind Child | Levon Helm | 3:26 | ||
| The Road Goes On Forever | Joe Ely | 4:33 | ||
| Gallo Del Cielo | Joe Ely | 7:03 | ||
| Down the Rio Grande | Tom Russell | 5:37 | ||
| Old Dance Floor | John R. Miller | 4:23 | ||
