| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| Pack up Your Sorrows | Loudon Wainwright III, Iris DeMent | 2:44 | |
| A Summer Wind, A Cotton Dress | Richard Shindell | 3:55 | |
| Hurricane Party | James McMurtry | 5:56 | |
| Letting People Down | Lori McKenna | 2:56 | |
| Heartache Is an Uphill Climb | Tift Merritt | 3:14 | |
| I Was Drunk | Alejandro Escovedo | 4:53 | |
| Too Many Memories - (feat. Emmylou Harris) | Tom Rush | 3:42 | |
| Ten Year Night | Lucy Kaplansky | 5:12 | |
| You Give it All Away | Dar Williams | 2:47 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Feel of the World | Tift Merritt, Simone Dinnerstein | 4:33 | |
| Infamous Angel | Iris DeMent | 3:46 | |
| Shotgun Hearts | Amy Speace, The Orphan Brigade | 4:46 | |
| Might As Well Dance | Patty Larkin | 3:20 | |
| Sweet Tequila Blues | Chip Taylor, Carrie Rodriguez | 3:15 | |
| To Myself | Tift Merritt | 3:34 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Promises to Keep | Eliza Gilkyson | 4:23 | |
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | |
| Stitch of the World | Tift Merritt | 3:54 | |
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| I Saw A Stranger With Your Hair | John Gorka | 4:03 | |
| Farewell to Fiddler's Rim | Dave Carter, Tracy Grammer | 2:12 | |
| When You Need a Train It Never Comes | Amanda Shires | 4:14 | |
| Bowling Green | Neko Case, Her Boyfriends | 2:17 | |
| Not Lonely | Eliza Gilkyson | 4:13 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Levelland | James McMurtry | 5:23 | |
| How Quickly Your Heart Mends | Courtney Marie Andrews | 3:45 | |
| Killing the Blues | Chris Smither | 5:49 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| Station To Station | Jay Farrar | 2:39 | |
| After the Rain | Chuck Prophet | 3:35 | |
| It Makes No Difference | Shannon McNally | 5:27 | |
| Can't Hardly Wait | Justin Townes Earle | 2:48 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| All My Money On You | Diana Jones | 3:09 | |
| If I Could Make You My Own | Dori Freeman | 3:22 | |
| Counting the Hours | Two Dollar Pistols, Tift Merritt | 3:42 | |
| It's Enough (feat. Tift Merritt) | Michael Wexler, Tift Merritt | 3:35 | |
| P-Town | Lilly Hiatt | 2:46 | |
| Afraid | Ted Hawkins | 4:36 | |
| Where I Am Now | Shelby Lynne | 3:40 | |
| Lovin' In My Baby's Eyes | Shannon McNally | 3:56 | |
| Neighborhood | Tift Merritt | 3:19 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Inside | Bill Morrissey | 2:59 | |
| Black Sheep | Blackie & The Rodeo Kings, Serena Ryder | 5:28 | |