| The Road To Ensenada | Lyle Lovett | 4:15 | |
| Let's Leave This Town | Chip Taylor, Carrie Rodriguez | 3:23 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| Tell Me A Story | Po' Girl | 3:13 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| Our Town | Iris DeMent | 5:00 | |
| Song to Woody | Bob Dylan | 2:40 | |
| Me and Bobby McGee | Gordon Lightfoot | 3:46 | |
| East of Eden | Tom Rush | 3:29 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Workin' On A World | Iris DeMent | 3:49 | |
| Shelter from the Storm | Bob Dylan | 5:01 | |
| This Land is Your Land | Woody Guthrie | 2:19 | |
| Ern & Zorry's Sneakin' Bitin' Dog | Dori Freeman | 2:10 | |
| Eastern Light (feat. Sam Beam) | Tift Merritt, Sam Beam | 4:34 | |
| I'll Take My Sorrow Straight | Iris DeMent | 3:27 | |
| Do You Ever Think of Me | Laura Cantrell | 2:44 | |
| Somebody Else's Troubles | Steve Goodman | 3:43 | |
| Old Friend | Lyle Lovett | 3:13 | |
| Carmelita | Warren Zevon | 3:34 | |
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| If I Cant Win | The Cactus Blossoms | 3:17 | |
| It's Not Happening | The Be Good Tanyas | 2:41 | |
| Romeo's Tune | Steve Forbert | 3:32 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| If I Were a Bluebird | Linda Thompson | 6:50 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| A Smell Of Coffee | Greg Brown | 3:53 | |
| It Is What It Is | Malcolm Holcombe, Iris DeMent | 5:00 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Pack up Your Sorrows | Loudon Wainwright III, Iris DeMent | 2:44 | |
| Mama Needs a Margarita | Zoe Muth | 4:06 | |
| Let's Invite Them Over (feat. Iris DeMent) | John Prine, Iris DeMent | 2:11 | |
| Unknown Legend | Neil Young | 4:32 | |
| Heart Like a Wheel | Kate & Anna McGarrigle | 3:12 | |
| The Littlest Birds | The Be Good Tanyas | 4:09 | |
| A Thousand Miles | Erika Lewis | 2:53 | |
| Urge for Going - 2008 Remaster | Tom Rush | 5:51 | |
| The Roseville Fair | Bill Staines | 3:32 | |
| Something In The Rain | Tish Hinojosa | 5:03 | |
| Mercy Now | Mary Gauthier | 5:50 | |
| Every Time You Say Goodbye | Alison Krauss & Union Station | 3:18 | |
| Who Carried You | Malcolm Holcombe | 3:31 | |
| I Don't Believe You've Met My Baby | Jerry Douglas | 3:13 | |
| Afraid | Ted Hawkins | 4:36 | |
| I Dream Of Highways | Hoyt Axton | 2:35 | |
| The Bramble And The Rose | Mary McCaslin, Jim Ringer | 3:18 | |
| Broken | Tift Merritt | 3:44 | |