| Missin' You | Little Feat | 2:21 | |
| After the Storm | The Flatlanders | 3:52 | |
| New York City's Killing Me (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:13 | |
| Sunday Morning Coming Down | Kris Kristofferson | 5:19 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Darkest Hour | Bob Weir | 3:24 | |
| Pale Blue Eyes | Alejandro Escovedo | 6:15 | |
| Pick Up the Tempo | Waylon Jennings, Willie Nelson | 2:34 | |
| Rock Island Line | Billy Bragg, Joe Henry | 2:55 | |
| Green, Green Rocky Road | Dave Van Ronk | 3:42 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| Cool Cool Rain | Ray Bonneville | 3:46 | |
| Running Up The Stairs | Leo Kottke | 3:15 | |
| The Hula Hula Boys - 2007 Remaster | Warren Zevon | 3:02 | |
| On the Banks of the Old Kishwaukee | Ryley Walker | 5:00 | |
| Ghost Repeater | Jeffrey Foucault | 5:10 | |
| Die When I'm High (Halfway to Heaven) | Particle Kid, Micah Nelson, Willie Nelson | 3:32 | |
| The Pilgrim, Chapter 33 | Kris Kristofferson | 3:09 | |
| Lay Me Down (with Willie Nelson) | Loretta Lynn, Willie Nelson | 2:50 | |
| Oh Soul | Mary Gauthier | 5:26 | |
| Heaven and Hell | Waylon Jennings, Willie Nelson | 1:38 | |
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| Rexanimarum | Israel Nash | 4:59 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Crawling Back To You | Tom Petty | 5:05 | |
| The Night Shift Lullaby | Magnolia Electric Co., Jason Molina | 4:33 | |
| Homeland Refugee | The Flatlanders | 3:58 | |
| Blue Skies | Willie Nelson | 3:33 | |
| Stab At Matter | Bruce Cockburn | 3:44 | |
| Love Will Win the War | Darden Smith | 3:54 | |
| Over You | T Bone Burnett | 2:20 | |
| Not A Dry Eye In The House | Jeannie Seely, Willie Nelson | 3:47 | |
| Red Dress | Israel Nash | 4:07 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Take It Easy | Jackson Browne | 3:51 | |
| Heaven Help The Child | Bill Callahan | 5:07 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| On The Road Again | Alanis Morissette, Willie Nelson | 2:19 | |
| I Am the Light of This World | Jorma Kaukonen | 3:48 | |
| I Make The Dough, You Get The Glory | Kathleen Edwards | 4:37 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Out In The Rain | Julie Miller | 4:20 | |
| Straight Street | Ry Cooder | 4:00 | |
| I Misunderstood | Richard Thompson | 4:05 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Don't Take Your Guns To Town - Live | Johnny Cash, Willie Nelson | 4:42 | |
| Goin' Down To Memphis - Demo Version | John Martyn | 3:01 | |
| Asking For Flowers | Kathleen Edwards | 5:02 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| Trouble Over Me | Tift Merritt | 5:08 | |