| Airplane | David Rawlings | 4:44 | |
| Lost (For As Long As I Live) | Daniel Romano | 3:06 | |
| Kathleen | Josh Ritter | 4:08 | |
| Our Town | Iris DeMent | 5:00 | |
| She - 2002 Remaster | Gram Parsons | 5:01 | |
| Love Me Tenderly | The Felice Brothers | 3:40 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Just Like Heaven | The Infamous Stringdusters | 4:08 | |
| Everybody's Missing the Sun | The Gourds | 2:59 | |
| The Trip | Dave Rawlings Machine | 10:55 | |
| Stadium Inn | Jonny Fritz | 2:44 | |
| Hey Stranger | Watchhouse | 3:27 | |
| Willin' | Little Feat | 2:54 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Hymn #101 | Joe Pug | 4:40 | |
| James Alley Blues | Willie Watson | 4:06 | |
| Pinnacle Mountain Silver Mine | Jake Xerxes Fussell | 4:18 | |
| Clay Pigeons | Blaze Foley | 3:00 | |
| Strange Faces | Daniel Romano | 3:00 | |
| I Don't Fall Much, Anymore | Barna Howard | 3:44 | |
| She Loves Me | James McMurtry | 3:01 | |
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| Mama | Lula Wiles | 3:18 | |
| Raggy Levy | Jake Xerxes Fussell | 3:59 | |
| Old Fires | Daniel Romano | 3:38 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| When A Cowboy Trades His Spurs For Wings | Gillian Welch, David Rawlings | 3:03 | |
| Quite a Feelin' | Barna Howard | 4:09 | |
| Private Property | Langhorne Slim | 2:02 | |
| Long Time Gone | Darrell Scott, Tim O'Brien | 3:36 | |
| I've Got a Name for the Newborn Child | Hiss Golden Messenger | 3:12 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Method Acting / Cortez The Killer | Dave Rawlings Machine | 10:20 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| Two Daughters and a Beautiful Wife | Drive-By Truckers | 3:05 | |
| Pork and Beans | Jake Xerxes Fussell | 4:02 | |
| Mostly Water | Bap Kennedy | 3:23 | |
| Lonesome LA Cowboy | Mapache | 4:32 | |
| Stoplight Kisses | The Cactus Blossoms | 2:17 | |
| Goodnight Rhonda Lee | Nicole Atkins | 2:33 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Me and My Uncle | The Lone Bellow | 3:04 | |
| First Air of Autumn | Drive-By Truckers | 3:30 | |
| Rachel's Song | James McMurtry | 4:39 | |
| Won't Be Long | The Infamous Stringdusters, Sara Jarosz | 3:16 | |
| It's Too Easy | Dave Rawlings Machine | 3:08 | |
| Cold Canary Gaslight | Marty O'Reilly & the Old Soul Orchestra | 4:42 | |
| King Of California | Dave Alvin | 4:50 | |
| Girl Of The North Country | Sam Bush | 5:17 | |
| Angel Eyes | Willis Alan Ramsey | 3:11 | |