| People Get Old | Lori McKenna | 3:42 | |
| Missin' You | Little Feat | 2:21 | |
| Beautiful Scars | Blackie & The Rodeo Kings, City and Colour | 4:55 | |
| Bulbs | Van Morrison | 4:18 | |
| Stripping Cane | Jeffrey Foucault | 4:25 | |
| River Song | Tom Rush | 3:56 | |
| Coconut Tree (with Willie Nelson) | Kenny Chesney, Willie Nelson | 3:24 | |
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | |
| Take It to the Limit | Waylon Jennings, Willie Nelson | 3:46 | |
| Both Sides Now | Willie Nelson | 3:01 | |
| (Looking For) The Heart Of Saturday Night | Tom Waits | 3:53 | |
| Running Up The Stairs | Leo Kottke | 3:15 | |
| Songbird | Eric Clapton, Willie Nelson | 2:55 | |
| Got Your Six | Mary Gauthier | 2:38 | |
| Heaven Help The Child | Bill Callahan | 5:07 | |
| Not A Dry Eye In The House | Jeannie Seely, Willie Nelson | 3:47 | |
| Free To Go | Neal Casal | 6:03 | |
| That's What Makes The World Go Around | Charley Crockett, Willie Nelson | 3:17 | |
| Time To Move On | Tom Petty | 3:15 | |
| Grave Angels | Joe Henry | 5:31 | |
| Mandolin Wind | Amy Helm | 5:52 | |
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| Me and Bobby McGee | Kris Kristofferson | 4:20 | |
| Sunday Mornin' Comin' Down | Willie Nelson | 7:02 | |
| The War After the War | Mary Gauthier | 3:44 | |
| Old Shoes | Tom Waits | 4:25 | |
| Please Tell My Brother | Golden Smog | 2:10 | |
| Rex's Blues | Son Volt - Jay Farrar & Kelly Willis | 4:40 | |
| Adios to California | John Hiatt | 3:47 | |
| It's My Lazy Day | Merle Haggard, Willie Nelson | 2:49 | |
| The Year 2003 Minus 25 - Remastered | Waylon Jennings, Willie Nelson | 3:04 | |
| For Everyman | Jackson Browne | 6:12 | |
| Our Song | Willie Nelson | 3:51 | |
| Long Black Veil - Remastered 2000 | The Band | 3:01 | |
| King's Highway | Joe Henry | 3:47 | |
| Everywhere I Go | Willie Nelson | 3:50 | |
| East of Woodstock, West of Viet Nam | Tom Russell | 4:24 | |
| I Know Love Is All I Need | Rodney Crowell | 5:20 | |
| Come What May | Colvin & Earle | 3:11 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
| These Lonely Nights | Willie Nelson | 3:29 | |
| When I Cross Over | Tift Merritt | 6:32 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| El Camino Reprise | Amos Lee, Willie Nelson | 4:14 | |
| Willin' | Linda Ronstadt | 3:02 | |
| Turn Off The News (Build A Garden) | Lukas Nelson and Promise of the Real | 3:43 | |
| The Maker | Willie Nelson | 5:08 | |
| Laid A Highway | Tift Merritt | 3:53 | |
| Anna Lee | Levon Helm | 3:42 | |
| Four In The Morning | Jesse Colin Young | 3:25 | |
