| Workin’s Too Hard | Rayna Gellert | 3:36 | |
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | |
| Let's Invite Them Over (feat. Iris DeMent) | John Prine, Iris DeMent | 2:11 | |
| Stoplight Kisses | The Cactus Blossoms | 2:17 | |
| Trouble (with Delbert McClinton) | Iris DeMent, Delbert McClinton | 7:33 | |
| 'Til It's Over | The Secret Sisters | 2:56 | |
| West Texas Heaven | Kimmie Rhodes | 3:07 | |
| Midnight Train | David Rawlings | 3:18 | |
| Somebody Else's Troubles | Steve Goodman | 3:43 | |
| No Regrets - 2008 Remaster | Tom Rush | 3:51 | |
| Always | John Gorka | 3:55 | |
| Hobo's Lullaby | Billy Bragg, Joe Henry | 3:57 | |
| The Way I Should | Iris DeMent | 4:26 | |
| Do It | Jesse Winchester | 1:27 | |
| Moonshiner | Uncle Tupelo | 4:23 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| Lavender Blue (with Iris Dement) | Keith Sykes, Iris DeMent | 3:05 | |
| Down in My Hometown | The Flatlanders | 2:45 | |
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| No Depression | Uncle Tupelo | 2:20 | |
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| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Canola Fields | James McMurtry | 4:49 | |
| Live Forever | Billy Joe Shaver | 2:49 | |
| What Do We Do Now | John Hiatt | 2:58 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| I Threw It All Away | Bob Dylan | 2:23 | |
| Please Help Me, I'm Falling | Kieran Kane, Rayna Gellert | 3:34 | |
| What They Say | Chris Smither | 2:46 | |
| Hey Little Darlin' | Zoe Muth | 3:30 | |
| Something Less Than Something More | Caitlin Cary, Thad Cockrell | 5:08 | |
| Bye Bye Montreal | Amelia Curran | 2:46 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| Those Memories of You - 2015 Remaster | Dolly Parton, Linda Ronstadt, Emmylou Harris | 4:00 | |
| Enjoy Yourself | Todd Snider | 3:27 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| Boulder to Birmingham - 2003 Remaster | Emmylou Harris | 3:33 | |
| I've Got That Old Time Religion in My Heart | Iris DeMent | 3:04 | |
| All I Ever Wanted | Dori Freeman | 3:41 | |
| A Crooked Road | Darrell Scott | 4:11 | |
| Helpless | Molly Tuttle, Old Crow Medicine Show | 4:25 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| I Don't Want to Get Adjusted to This World | Iris DeMent | 3:38 | |
| Light Enough to Travel | The Be Good Tanyas | 4:58 | |
| Beeswing | Richard Thompson | 5:33 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| In The Real West | Tish Hinojosa | 2:48 | |
| The Weary Kind | Ryan Bingham | 4:18 | |
| Poncho & Lefty | Townes Van Zandt | 3:40 | |