| Dream Café | Greg Brown | 5:57 | |
| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | |
| Look at Us (feat. Morgane Stapleton) | John Prine, Morgane Stapleton | 2:46 | |
| Jesus Take the Wheel (and Drive Me to a Bar) | Sam Outlaw | 3:19 | |
| Round and Round - Original Mono Single Version | Walker Jerry Jeffrey | 3:14 | |
| Winsome Smile | Chris Smither | 3:34 | |
| In a Razor Town | Jason Isbell | 3:19 | |
| Fishin' with You | Carsie Blanton | 2:16 | |
| Wouldn't It Be Great? | Loretta Lynn | 3:24 | |
| Never Had It So Good | Mary Chapin Carpenter | 4:04 | |
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | |
| Spring Wind | Greg Brown | 4:34 | |
| The Long Black Veil | Lefty Frizzell | 3:08 | |
| Jenny Reprise | Chip Taylor, Carrie Rodriguez | 3:33 | |
| These Cowboys Born out of Their Time | Gretchen Peters | 4:12 | |
| Cowboy Singer | Dave Carter, Tracy Grammer | 3:44 | |
| Blue Mountains of Mexico | Gretchen Peters | 3:37 | |
| Hearts on Fire - 2002 Remaster | Gram Parsons | 3:52 | |
| You'll Never Leave Harlan Alive | Patty Loveless | 6:05 | |
| High Country Snows | Dan Fogelberg | 4:45 | |
| Ain't Glad I'm Leaving | Justin Townes Earle | 2:32 | |
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| Andy Devine | Dave Stamey | 4:08 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Cry To Me | John Hiatt | 3:55 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Perfect Timing | Drive-By Truckers | 2:57 | |
| Infamous Angel | Iris DeMent | 3:46 | |
| Country Morning Music | Keith Sykes | 2:27 | |
| Tell the Devil I'm Gettin' there as Fast as I Can | Ray Wylie Hubbard | 5:47 | |
| Goodbye Old Paint | Don Edwards, Peter Rowan | 4:14 | |
| None'ya | Hayes Carll | 3:28 | |
| If I Had Known | Greg Brown | 3:25 | |
| Amazing Grace (Used to Be Her Favorite Song) - Remastered | Amazing Rhythm Aces | 3:17 | |
| Let's Take a Vacation | Joshua Hedley | 3:51 | |
| If I Needed You | Jason Isbell & Amanda Shires | 2:46 | |
| Long Black Veil | Lefty Frizzell | 3:02 | |
| Let Me Die in My Footsteps | Steep Canyon Rangers | 3:23 | |
| Big Moon Shinin' | Chip Taylor, Carrie Rodriguez | 6:15 | |
| How Much I've Lied - 2002 Remaster | Gram Parsons | 2:29 | |
| The Last Cowboy Song | Ed Bruce | 4:57 | |
| Walk On Boy | Doc Watson | 3:23 | |
| For Lovin' Me | Gordon Lightfoot | 2:27 | |
| Stars Fell On Alabama | Tara Nevins | 2:56 | |
| All Just To Get To You | Joe Ely | 4:15 | |
| Tennessee Stud - Vanguard Version | Doc Watson | 3:37 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| She Came From Fort Worth | Kathy Mattea | 3:33 | |
| Who Carried You | Malcolm Holcombe | 3:31 | |
| Just Say She's A Rhymer | Mary Gauthier | 4:17 | |