| Grandpa Was a Carpenter | John Prine | 2:52 | |
| Champaign, Illinois | Old 97's | 3:25 | |
| Shanty | Jonathan Edwards | 2:35 | |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| This Land is Your Land | Woody Guthrie | 2:19 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Tupelo | Jason Isbell and the 400 Unit | 4:01 | |
| Mountain Dew - Original Gusto Recordings | The Stanley Brothers | 2:43 | |
| You Never Even Call Me By My Name | Steve Goodman | 4:19 | |
| Speed Of The Sound Of Loneliness | John Prine | 3:28 | |
| Mexican Cowboy | Willie Watson | 3:53 | |
| Tulsa County - Single Version | Son Volt | 2:53 | |
| Let Me Die in My Footsteps | Steep Canyon Rangers | 3:23 | |
| Fishin' Blues | Taj Mahal | 3:04 | |
| In Bloom | Sturgill Simpson | 4:00 | |
| Ab's Song | The Marshall Tucker Band | 1:15 | |
| Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone) | John Prine | 4:05 | |
| Hickory Wind | The Byrds | 3:31 | |
| Victory | Trampled by Turtles | 3:57 | |
| 1952 Vincent Black Lightning | The Del McCoury Band | 4:02 | |
| Donald And Lydia | Steve Goodman | 4:51 | |
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| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Wishing All These Things Were New | Merle Haggard | 3:20 | |
| The Midnight Special | Billy Bragg, Joe Henry | 3:34 | |
| Still Fighting the War | Slaid Cleaves | 2:56 | |
| Oklahoma Hills - Remastered | Arlo Guthrie | 3:27 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| I'm on Fire | Whitey Morgan and the 78's | 3:16 | |
| Paradise | John Prine | 3:15 | |
| Wildflowers | Trampled by Turtles | 2:48 | |
| Bob | Drive-By Truckers | 2:15 | |
| Unknown Legend | Shovels & Rope, Shakey Graves | 4:28 | |
| Sweet Evangelina | Hoyt Axton | 3:11 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| White Trash | Fred Eaglesmith | 2:22 | |
| Midnight Special | Willie Watson | 4:38 | |
| You're Dreaming | The Cactus Blossoms | 3:25 | |
| Memories | Swamp Dogg, John Prine | 4:47 | |
| Willin' | Linda Ronstadt | 3:02 | |
| Can't Let Go | Lucinda Williams | 3:28 | |
| Just Outside Of Austin | Lukas Nelson and Promise of the Real | 4:44 | |
| Ophelia - Remastered 2000 | The Band | 3:32 | |
| Taking Water | Billy Strings | 4:08 | |
| Amtrak Crescent | Scott Miller | 4:41 | |
| The Bottle Let Me Down | Merle Haggard & The Strangers | 2:48 | |
| Another Like You | Hayes Carll | 3:19 | |
| Gone Gone Gone (Done Moved On) | Robert Plant, Alison Krauss | 3:32 | |
| Please Be With Me | Cowboy | 3:42 | |
| Broke Down | Slaid Cleaves | 3:10 | |