| Train to Birmingham | Kevin Welch | 4:13 | |
| East Virginia Blues | Robert Earl Keen | 3:34 | |
| See the Elephant | James McMurtry | 4:25 | |
| I'm Gone | Pieta Brown | 2:20 | |
| Worried Mind | Eilen Jewell | 3:15 | |
| I Want My Dog To Live Longer (The Greatest Wish) | Curtis Salgado, Alan Hager | 2:47 | |
| Snowin' on Raton | Gretchen Peters | 4:23 | |
| Marion and Sam | John Leventhal | 1:06 | |
| Mean Ol' Wind Died Down | Luther Dickinson | 4:00 | |
| Dusty Boxcar Wall | Eilen Jewell | 2:43 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| The Most Unoriginal Sin | John Hiatt & The Goners | 4:15 | |
| After the Storm | The Flatlanders | 3:52 | |
| Billy 4 | Gretchen Peters | 5:36 | |
| I Am the Big Easy | Ray Bonneville | 4:37 | |
| Looking at the World Through a Windshield | Son Volt | 3:08 | |
| Saving the Good Stuff for You | Richard Thompson | 3:54 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Dangerous Fun | Jesse Winchester | 2:05 | |
| Rocks into Sand | Bill Kirchen | 3:26 | |
| Rosalie | Alejandro Escovedo | 3:49 | |
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| Lost John Dean | Kieran Kane, Kevin Welch, Fats Kaplin | 3:26 | |
| The Piano Has Been Drinkin' (Not Me) | Dan Hicks & His Hot Licks | 3:30 | |
| Sitting on Top of the World | Tim Easton | 2:54 | |
| Crawl | Eilen Jewell | 3:38 | |
| Dark Eyed Gal (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:58 | |
| My Best Girl | Tom Rush | 2:53 | |
| Do You Know? | Pieta Brown, Amos Lee | 3:01 | |
| The Wonder of You | Chip Taylor, Carrie Rodriguez | 4:02 | |
| Dreamer | Amy LaVere, Will Sexton | 2:52 | |
| Let the Mystery Be | Greg Brown | 4:05 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| Every Day | Will Kimbrough | 2:52 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| Just Like That (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:30 | |
| White Freight Liner Blues | Tommy Emmanuel, Molly Tuttle | 4:16 | |
| Ain't Glad I'm Leaving | Justin Townes Earle | 2:32 | |
| Rock Island Line | Billy Bragg, Joe Henry | 2:55 | |
| Do It | Jesse Winchester | 1:27 | |
| Big Moon Shinin' | Chip Taylor, Carrie Rodriguez | 6:15 | |
| Fishing With Bill | Bill Morrissey, Greg Brown | 4:32 | |
| Bourbon Hound | Della Mae, Molly Tuttle, Avril Smith | 3:11 | |
| Gentleman Of Leisure | Jesse Winchester | 3:52 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Rock Salt And Nails | Buddy & Julie Miller | 4:17 | |
| End-Titles | John Leventhal | 3:47 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
| I Dream Of Highways | Hoyt Axton | 2:35 | |
| Motherless Children | Rosanne Cash | 3:06 | |