| It's a Big Old Goofy World | John Prine | 5:10 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| The Love That We Need | Hayes Carll | 4:08 | |
| Desperado | The Cactus Blossoms | 2:46 | |
| Feelin' Good Again | Robert Earl Keen | 3:16 | |
| Clay Pigeons | John Prine | 4:27 | |
| 18 Wheels | Fred Eaglesmith | 5:01 | |
| Shame on the Moon | Rodney Crowell | 4:40 | |
| Tell the Devil I'm Gettin' there as Fast as I Can | Ray Wylie Hubbard | 5:47 | |
| Life Worth Livin' | Uncle Tupelo | 3:32 | |
| California Stars - Live | Wilco | 3:45 | |
| Desperados Waiting For A Train | Guy Clark | 4:29 | |
| Sixteen Angels Dancing 'Cross the Moon | Chip Taylor, John Prine | 3:18 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| Seven Bridges Road | Iain Matthews | 4:05 | |
| Terms of My Surrender | John Hiatt | 3:29 | |
| Still Fighting the War | Slaid Cleaves | 2:56 | |
| South Wind of Summer | The Flatlanders | 4:46 | |
| The War After the War | Mary Gauthier | 3:44 | |
| Amarillo Highway (for Dave Hickey) | Terry Allen | 4:00 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
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| Angel from Montgomery - Live | Susan Tedeschi | 6:33 | |
| Time Stands Still | Chris Smither | 3:45 | |
| Dusty Old Man | Tift Merritt | 3:47 | |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Lovin' in My Baby's Eyes | Taj Mahal | 2:40 | |
| Visions Of Johanna | Chris Smither | 5:22 | |
| Oh My Sweet Carolina | Ryan Adams | 4:56 | |
| Fat Man in the Bathtub | Little Feat | 4:31 | |
| Crossing Muddy Waters | I'm With Her, Sara Watkins, Sarah Jarosz, Aoife O'Donovan | 3:48 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Tomorrow’s Gonna Be a Brighter Day | Jim Croce | 2:53 | |
| It Probably Always Will | The Ozark Mountain Daredevils | 3:13 | |
| Boy From Oklahoma | Willis Alan Ramsey | 3:54 | |
| Come What May | Colvin & Earle | 3:11 | |
| The Weight - Remastered 2000 | The Band | 4:34 | |
| Ladder Of Success | Ted Hawkins | 3:26 | |
| Whenever Kindness Fails | Joe Ely | 4:05 | |
| Mercy Now | Mary Gauthier | 5:50 | |
| The Night They Drove Old Dixie Down | The Band | 3:31 | |
| Will The Circle Be Unbroken (Glory, Glory) | Nitty Gritty Dirt Band, Alison Krauss, Doc Watson, Taj Mahal | 4:39 | |
| Don't Make Me Explain It | Ted Hawkins | 2:37 | |
| Farewell Angelina | Tim O'Brien | 4:23 | |
| Wild Horses | Leon Russell | 3:37 | |
| Cold & Bitter Tears | Ted Hawkins | 2:14 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Drop In A Bucket | Mary Gauthier | 4:10 | |
| Too Drunk To Dream | Whiskeytown | 2:53 | |