| Helpless | k.d. lang | 4:17 | |
| My Winding Wheel | Ryan Adams | 3:12 | |
| Morning Song for Sally | Nanci Griffith | 4:55 | |
| Gauzy Dress in the Sun | Richard Buckner | 3:11 | |
| Prayer in Open D | Shannon McNally | 3:55 | |
| Long Way | Antje Duvekot | 6:07 | |
| Hickory Wind | Buddy Miller, Lucinda Williams | 4:42 | |
| You Might As Well | Sera Cahoone | 3:12 | |
| Off And Running | James McMurtry | 3:54 | |
| Workin’s Too Hard | Rayna Gellert | 3:36 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Our Song | Joe Henry | 6:19 | |
| Simple Twist of Fate | Jeff Tweedy | 3:43 | |
| Betting On Trains | Hem | 2:44 | |
| Christchurch Woman | Justin Townes Earle | 4:11 | |
| Hell Or High Water (feat. Lucinda Williams) | Mike Campbell & The Dirty Knobs, Lucinda Williams | 4:38 | |
| My Favorite Picture of You | Guy Clark | 3:32 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Six Blocks Away | Lucinda Williams | 2:52 | |
| Looking For A Place To Land | Justin Townes Earle | 3:28 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
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| The Asp and the Albatross | Freakwater | 3:10 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Wide River to Cross | Buddy Miller | 3:03 | |
| Let the Mystery Be | Iris DeMent | 2:50 | |
| Pale Moon | Shannon McNally, Neal Casal | 4:39 | |
| Closer To The Light | Bruce Cockburn | 4:10 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Poor Girl - Klein | Po' Girl | 3:10 | |
| California | Jay Farrar | 4:21 | |
| Quiet Corners & Empty Spaces | The Jayhawks | 3:06 | |
| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| Steal Your Love | Lucinda Williams | 3:15 | |
| Handsome Molly | Bill Morrissey | 3:33 | |
| Metal Firecracker | Lucinda Williams | 3:30 | |
| I'm Still Loving You | Blackie & The Rodeo Kings | 4:27 | |
| Over My Shoulder | The Jayhawks | 3:40 | |
| Adieu False Heart | Linda Ronstadt, Ann Savoy | 3:34 | |
| Sweet Illusions | Ryan Adams & The Cardinals | 5:01 | |
| Lonely Girls | Lucinda Williams | 4:02 | |
| Angelyne | The Jayhawks | 3:43 | |
| Always A Friend | Alejandro Escovedo | 3:35 | |
| Buttercup | Lucinda Williams | 3:50 | |
| Stumbling Through The Dark | The Jayhawks | 2:24 | |
| I Cry Everyday | Shelby Lynne | 4:18 | |
| Essence | Lucinda Williams | 5:51 | |
| Whispering Pines | Boz Scaggs, Lucinda Williams | 4:20 | |
| River Of Love | T Bone Burnett | 3:31 | |