| Left Alone | Malcolm Holcombe, Iris DeMent | 4:11 | |
| Trouble Will Soon Be Over | Sinéad O'Connor | 3:18 | |
| I'll Take My Sorrow Straight | Iris DeMent | 3:27 | |
| Little Boxes | Pete Seeger | 1:54 | |
| Swimming Song | Kate & Anna McGarrigle | 2:29 | |
| Brighter Than the Blues | Joan Shelley | 3:17 | |
| One Red Rose | Iris DeMent | 3:07 | |
| Dangerous Fun | Jesse Winchester | 2:05 | |
| The Road To Ensenada | Lyle Lovett | 4:15 | |
| Simple Gearle | Stacey Earle | 2:30 | |
| That's Where I'm From | Robbie Fulks | 6:08 | |
| Ruby | Dave Rawlings Machine | 4:54 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Turns Around the Bottle | Barna Howard | 2:52 | |
| Genesis | Jorma Kaukonen | 4:18 | |
| Ridin' That Midnight Train | Ralph Stanley, Friends, Iris DeMent | 2:37 | |
| Go On Ahead and Go Home | Iris DeMent | 3:44 | |
| Hello in There | John Prine | 4:32 | |
| Streets of Baltimore - 2007 Remaster | Gram Parsons | 2:55 | |
| Tower of Song | Leonard Cohen | 5:39 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
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| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | |
| In Spite of Ourselves (feat. Iris DeMent) | John Prine, Iris DeMent | 3:33 | |
| The Devil's Paintbrush Road | The Wailin' Jennys | 3:47 | |
| My Good Gal | Old Crow Medicine Show | 4:18 | |
| Torn and Wrinkled | Malcolm Holcombe, Iris DeMent | 3:15 | |
| Our Song | Joe Henry | 6:19 | |
| Early Morning Rain | Gordon Lightfoot | 3:18 | |
| Me & Jiggs | Josh Ritter | 3:04 | |
| Bury Me Under the Weeping Willow | Natalie Merchant | 3:20 | |
| Eliza Jane | Eliza Gilkyson | 4:02 | |
| Duncan | Paul Simon | 4:43 | |
| No Regrets - 2008 Remaster | Tom Rush | 3:51 | |
| Dirty Dishes | Deer Tick | 3:17 | |
| Short Haired Woman Blues | Dave Rawlings Machine | 6:43 | |
| Man Over | Robinella and the CCstringband | 3:57 | |
| It's Just You (with Iris Dement) | Keith Sykes, Iris DeMent | 3:21 | |
| For The Turnstiles | The Be Good Tanyas | 4:26 | |
| Fill My Way With Love | Iris DeMent | 3:02 | |
| Stand By Your Man | Lyle Lovett | 2:43 | |
| Lily, Rosemary and the Jack of Hearts | Tom Russell | 9:44 | |
| Ingrid Bergman | Billy Bragg, Wilco | 1:50 | |
| Keep On The Sunny Side | The Whites | 3:34 | |
| Ghost Riders In The Sky | Mary McCaslin | 4:04 | |
| You Were On My Mind | Ian & Sylvia | 2:47 | |
| Love Has Come For You | Steve Martin, Edie Brickell | 3:08 | |
| Trouble | Yusuf / Cat Stevens | 2:52 | |
| You Are My Sunshine | Norman Blake | 4:27 | |
| Mercy Now | Mary Gauthier | 5:50 | |
