| Across the Borderline | Ry Cooder | 3:05 | |
| 4&20 Blues | Jeffrey Foucault | 2:58 | |
| Red Dog Tracks | Chip Taylor, Carrie Rodriguez | 4:47 | |
| After You're Gone | Iris DeMent | 4:04 | |
| Carmelita | Warren Zevon | 3:34 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Troublesome Waters | Iris DeMent | 5:15 | |
| I Was in the House When the House Burned Down | Warren Zevon | 3:04 | |
| It Is What It Is | Malcolm Holcombe, Iris DeMent | 5:00 | |
| Sunday Morning Coming Down | Kris Kristofferson | 5:19 | |
| Day In The Sun | Neal Casal | 5:02 | |
| Hey Baby Hey | Greg Brown | 3:28 | |
| Tennessee Whiskey | Harry Dean Stanton | 2:19 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Circle Back | John Hiatt & The Goners | 4:30 | |
| No Regrets - 2008 Remaster | Tom Rush | 3:51 | |
| It Must Be Someone Else’s Fault | Courtney Marie Andrews | 3:18 | |
| Quality Time | Iris DeMent | 4:05 | |
| Just Like That (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:30 | |
| City of New Orleans | Steve Goodman | 3:50 | |
| Espiritu Santo Bay | Kimmie Rhodes | 5:03 | |
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| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| Will the Circle be Unbroken | Michelle Wright, Iris DeMent, Mairéad Ní Mhaonaigh | 4:37 | |
| Broken Radio '22 | Jesse Malin, Bruce Springsteen | 3:41 | |
| Come Tomorrow | Patti Scialfa | 3:53 | |
| Who's Gonna Take the Garbage Out (feat. Iris DeMent) | John Prine, Iris DeMent | 2:41 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| Lucinda's Room | Aaron Lee Tasjan | 4:38 | |
| Hickory Wind | The Byrds | 3:31 | |
| Childhood Memories | Iris DeMent | 4:38 | |
| Here in California | Kate Wolf | 5:30 | |
| Across the Great Divide | Nanci Griffith | 3:57 | |
| West Texas Heaven | Kimmie Rhodes | 3:07 | |
| Fifty Miles of Elbow Room | Iris DeMent | 3:12 | |
| It's Just You (with Iris Dement) | Keith Sykes, Iris DeMent | 3:21 | |
| Growin' Pain | Peter Wolf | 3:12 | |
| The Night You Wrote That Song | Gretchen Peters | 4:55 | |
| Wreck You | Lori McKenna | 3:18 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| When the Night Falls (with Ry Cooder) - 2006 Remaster | T Bone Burnett, Ry Cooder | 3:57 | |
| Arguing With Ghosts | Gretchen Peters | 3:57 | |
| Juanita | The Flying Burrito Brothers | 2:30 | |
| Pallbearer | Josh Turner, Iris DeMent, Marty Stuart | 4:32 | |
| I'm Still Loving You | Blackie & The Rodeo Kings | 4:27 | |
| Gentleman Of Leisure | Jesse Winchester | 3:52 | |
| Trouble Over Me | Tift Merritt | 5:08 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Six O'Clock News | Kathleen Edwards | 4:36 | |
