| Kansas | Fred Eaglesmith | 3:44 | |
| One Red Rose | Iris DeMent | 3:07 | |
| Fathers and Mothers | Lukas Nelson and Promise of the Real | 5:21 | |
| The Truck Song | Lyle Lovett | 2:56 | |
| Needless To Say | Dana Cooper, Lyle Lovett | 3:10 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| A Horse In The Country | Cowboy Junkies | 3:50 | |
| East of Eden | Tom Rush | 3:29 | |
| The Most Unoriginal Sin | John Hiatt & The Goners | 4:15 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Where I Come From | Patty Griffin | 4:44 | |
| Moon On My Shoulder | Lyle Lovett | 2:20 | |
| Spring Wind | Greg Brown | 4:34 | |
| Sweet Old World | Lucinda Williams | 4:03 | |
| Missing Pieces | John Hiatt & The Goners | 4:06 | |
| Trouble (with Delbert McClinton) | Iris DeMent, Delbert McClinton | 7:33 | |
| The Whole Night Sky | Bruce Cockburn | 3:54 | |
| Nothing But A Good Ride | Lyle Lovett | 4:28 | |
| I Take My Chances | Mary Chapin Carpenter | 3:45 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Love Has No Pride - 2008 Remaster | Bonnie Raitt | 3:48 | |
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| Borderline | Eliza Gilkyson | 2:42 | |
| Circle Back | John Hiatt & The Goners | 4:30 | |
| The Ghost Of Tucumcari | Dana Cooper, Lyle Lovett | 3:11 | |
| Numbered Doors | Lori McKenna | 3:44 | |
| The Bug | Mary Chapin Carpenter | 3:47 | |
| Angel from Montgomery - Edit; Live at the Arie Crown Theater, Chicago, January, 1985 | Bonnie Raitt | 4:01 | |
| Last Train | Arlo Guthrie | 3:06 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Music You Mighta Made | Gurf Morlix | 4:37 | |
| Always | John Gorka | 3:55 | |
| The Girl I Left Behind Me (feat. The Avett Brothers) | Asleep At The Wheel, The Avett Brothers | 2:31 | |
| Boomtown | Greg Brown | 3:19 | |
| Carved In Stone | The Subdudes | 3:14 | |
| Walk Through The Bottomland | Lyle Lovett | 4:13 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| The Way I Should | Iris DeMent | 4:26 | |
| Tell Me One More Time | Kris Kristofferson | 2:39 | |
| Amtrak Crescent | Scott Miller | 4:41 | |
| The Beauty Way | Ray Wylie Hubbard | 3:29 | |
| The Girl I Left Behind | Levon Helm | 3:36 | |
| The American In Me | Steve Forbert | 4:09 | |
| Too Drunk To Dream | Whiskeytown | 2:53 | |
| Sweet Somewhere Bound | Jackie Greene | 4:59 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| Remember Me This Way | Steve Martin, Edie Brickell | 3:30 | |
| Drop In A Bucket | Mary Gauthier | 4:10 | |