| Postcard Blues | Cowboy Junkies | 3:22 | |
| Tupelo Pine | Tuba Skinny | 4:42 | |
| Harmony Two (feat. Shannon McNally) | Terry Allen, The Panhandle Mystery Band, Shannon McNally | 5:45 | |
| Old Wore out Cowboys (feat. Jamey Johnson & Willie Nelson) | Ward Davis, Jamey Johnson, Willie Nelson | 3:34 | |
| Moon River | Bill Orcutt | 1:30 | |
| A Clearing in the Field | William Tyler | 1:44 | |
| Mountain Banjo | Rhiannon Giddens | 2:41 | |
| Way Before the Time of Towns | Hoyt Axton | 3:06 | |
| Fryslan | Phil Cook | 3:23 | |
| California Sober (feat. Willie Nelson) | Billy Strings, Willie Nelson | 3:50 | |
| Steady Rain | Warren Zevon | 4:19 | |
| I Ain't Blue - 2008 Remaster | Bonnie Raitt | 3:36 | |
| The Open Road | Howe Gelb, Arizona Amp and Alternator | 1:14 | |
| Hong Kong Hillbilly AKA Nashville West | Clarence White | 1:56 | |
| Little Lady Blues | Daniel Bachman | 5:12 | |
| Write a Song a Song / Angeline | Mickey Newbury | 7:12 | |
| She's Not for You | Willie Nelson | 3:13 | |
| Betty | Fred Eaglesmith | 2:17 | |
| I Got It Bad (And That Ain't Good) | Nina Simone | 4:04 | |
| All My Love Is Gone | Lyle Lovett | 4:23 | |
| The Pilgrim, Chapter 33 | Kris Kristofferson | 3:09 | |
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| One More Cowboy (feat. Willie Nelson) | Dan Hicks & His Hot Licks, Willie Nelson | 4:03 | |
| Down in My Hometown | The Flatlanders | 2:45 | |
| In the Valley of the Sun | Marisa Anderson | 4:12 | |
| Songbird | Eric Clapton, Willie Nelson | 2:55 | |
| Lubbock Woman | Terry Allen | 3:36 | |
| Dallas | The Flatlanders | 3:01 | |
| Beginning | Dana Westover | 1:16 | |
| Snorkel | Leo Kottke | 3:24 | |
| Down to the Well | Kevin Gordon | 4:10 | |
| Big Joe And Phantom 309 | Tom Waits | 6:27 | |
| Peggy Day | Bob Dylan | 1:59 | |
| Bob the Bob | The Lounge Lizards | 2:07 | |
| Juliette | Jackson C. Frank | 4:42 | |
| The Truth Ain't In You | Larry Jon Wilson | 3:13 | |
| What I Want Is You | Cowboy | 3:28 | |
| World In Motion | Pops Staples | 3:57 | |
| Blue Smoke - Instrumental | Merle Travis | 2:28 | |
| Ou Es-Tu, Mon Amour? | Willie Nelson | 2:43 | |
| Cod'ine | Buffy Sainte-Marie | 5:07 | |
| My Old Timey Baby | Dan Hicks & His Hot Licks | 2:29 | |
| One-Dime Blues | Etta Baker | 2:35 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| Desperate Man Blues - Original Recording | John Fahey | 4:06 | |
| Pay Day | Mississippi John Hurt | 4:21 | |
| This Ain't The Blues | Speedy West | 2:09 | |
| Jesus Is A Dying Bedmaker | John Fahey | 4:19 | |
| The Maker | Willie Nelson | 5:08 | |
| Please Be With Me | Cowboy | 3:42 | |
