| White Girl | The Milk Carton Kids | 3:44 | |
| Good Hearted Woman | Waylon Jennings | 3:01 | |
| Songbird | Eric Clapton, Willie Nelson | 2:55 | |
| Cool Cool Rain | Ray Bonneville | 3:46 | |
| I'll Be All Right | Jorma Kaukonen | 3:08 | |
| Come A Long Way | Loudon Wainwright III | 2:46 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Desperados Under the Eaves | Warren Zevon | 3:43 | |
| Time of the Preacher | Willie Nelson | 2:25 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| The New Lee Highway Blues | David Bromberg | 5:39 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Refugee Blues | Aaron Lee Tasjan | 3:54 | |
| Wonderful Remark - Philosopher's Stone Version | Van Morrison | 8:01 | |
| Kristine | Joe Purdy | 3:54 | |
| Summertime Thing | Chuck Prophet | 5:11 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Running Up The Stairs | Leo Kottke | 3:15 | |
| First Air of Autumn | Drive-By Truckers | 3:30 | |
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| Feels Like Lightning | Josh Ritter | 3:02 | |
| Clay Pigeons | Blaze Foley | 3:00 | |
| I'm Gone | Pieta Brown | 2:20 | |
| Under Pressure | Karen O, Willie Nelson | 4:55 | |
| Gotta Serve Somebody | Jamey Johnson, Willie Nelson, Chris Stapleton, Lee Ann Womack | 8:07 | |
| The Long Time Now | T Bone Burnett | 2:57 | |
| Crop Comes In | Chatham County Line | 4:23 | |
| Dallas | The Flatlanders | 3:01 | |
| For The Turnstiles | The Be Good Tanyas | 4:26 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| When The Night Was Young | Robbie Robertson | 5:04 | |
| Willin' | Little Feat | 2:54 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| The River Knows Your Name | John Hiatt | 4:25 | |
| Fly High | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:45 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Jacksonville Skyline | Whiskeytown | 3:00 | |
| I Shall Be Released - Remastered 2000 | The Band | 3:12 | |
| Cardboard Boxes | Loudon Wainwright III | 3:15 | |
| Set Me Down On A Cloud | Lukas Nelson and Promise of the Real, Lucius | 7:16 | |
| Just Dropped In (To See What Condition My Condition Was In) | Willie Nelson | 3:42 | |
| River Of Love | T Bone Burnett | 3:31 | |
| My Own Peculiar Way | Willie Nelson | 3:37 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Entella Hotel | Peter Case | 4:58 | |
| Superman | Snoop Dogg, Willie Nelson | 2:05 | |
| I Just Can't Let You Say Good-Bye | Willie Nelson | 4:38 | |
