| Sinner's Prayer | Slaid Cleaves | 4:50 | ||
| Oh Sarah | Sturgill Simpson | 4:15 | ||
| Time Honored Tradition | Natalie Hemby | 3:16 | ||
| Ellis County | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:51 | ||
| Long Haired Tattooed Hippie Freak | Eleven Hundred Springs | 3:03 | ||
| Whim of Iron | Slaid Cleaves | 2:29 | ||
| Stars | Fred Eaglesmith | 3:16 | ||
| Rice Birds | Adam Carroll | 4:42 | ||
| Traveling Poor Boy | Brent Cobb | 3:34 | ||
| Dog - Audiotree Live Version | The Bottle Rockets, Audiotree | 2:21 | ||
| I'm Drinking Through It | Jack Ingram | 4:59 | ||
| Stars In California | Drew Kennedy | 5:00 | ||
| Primer Gray | Slaid Cleaves | 3:58 | ||
| Is Anybody Goin' to San Antone | Eleven Hundred Springs | 2:52 | ||
| What It Takes | Fred Eaglesmith | 3:57 | ||
| Let the Lead Fly | Wrinkle Neck Mules | 4:06 | ||
| Pine Grove (Madhouse) | Ian Noe | 4:05 | ||
| Ghosts of Our Fathers | Otis Gibbs | 3:46 | ||
| Home Is Where The Hurt Is | JP Harris | 3:10 | ||
| Weight of the World | Western Centuries | 3:22 | ||
| Cry | Slaid Cleaves | 3:52 | ||
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| Ten Miles Down the Nine Mile Road | Scott Miller | 4:13 | ||
| There Ain't No Easy Way | Tim O'Brien, Darrell Scott | 4:28 | ||
| Pirate | Callahan Divide | 4:52 | ||
| Roses by the Dozen | Jamie Lin Wilson | 3:46 | ||
| Bernadine (feat. Chris Carroll) | Adam Carroll, Chris Carroll | 4:31 | ||
| Bull Riders & Songwriters | Willy Tea Taylor | 5:15 | ||
| Spirit Rider | Jamey Johnson | 4:18 | ||
| Someday/Sometime | Scott Miller | 3:54 | ||
| Country Bound | Brent Cobb | 3:45 | ||
| The Only Thing She Left Me Was the Blues | Eleven Hundred Springs | 3:40 | ||
| Welding Burns | Slaid Cleaves | 3:23 | ||
| Aunt Peg's New Old Man | Robbie Fulks | 3:01 | ||
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | ||
| Minor Enough | Wrinkle Neck Mules | 3:20 | ||
| Delete and Fast Forward | Willie Nelson | 3:23 | ||
| Road to Nowhere | BJ Barham | 4:16 | ||
| Your Sister | Gurf Morlix | 2:37 | ||
| Piedmont Sky | Caleb Caudle | 3:00 | ||
| Black Maria | Three Tall Pines | 4:42 | ||
| Good Times | Charlie Robison | 3:56 | ||
| Big Whiskers | Otis Gibbs | 5:50 | ||
| Automatic | The Honeycutters | 4:17 | ||
| Ain't Gone Yet | William Elliott Whitmore | 5:19 | ||
| Letter To Laredo | Joe Ely | 4:39 | ||
| Bottom Of The World | Alejandro Escovedo | 3:04 | ||
| Midnight And Lonesome | Buddy Miller | 3:55 | ||
| Gallo Del Cielo - Live At Antone's, Austin, TX / January 22 & 23, 1999 | Joe Ely | 7:04 | ||
| Wishbones | Slaid Cleaves | 3:27 | ||
