| Little Things | William Prince | 4:19 | |
| Long Monday | John Prine | 3:22 | |
| Queen of Them All | The Cactus Blossoms | 3:40 | |
| Great American Roadside | Otis Gibbs | 2:49 | |
| Goddamn Lonely Love - Remastered | Drive-By Truckers | 5:01 | |
| Beautiful Thing | Slaid Cleaves | 3:16 | |
| Too Long (I've Been Gone) | Dom Flemons | 2:53 | |
| Souvenirs | John Prine | 3:37 | |
| Tell the Devil I'm Gettin' there as Fast as I Can | Ray Wylie Hubbard | 5:47 | |
| The Night That John Prine Died | John McCutcheon | 4:17 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Hobo's Lullaby | Arlo Guthrie | 3:57 | |
| Off This Mountaintop | Ian Noe | 3:32 | |
| If I Just Knew What to Say - Remastered | Amazing Rhythm Aces | 2:05 | |
| All That's Left Is Fare-Thee-Well (feat. Charlie Sexton) | Terry Allen, The Panhandle Mystery Band, Charlie Sexton | 3:06 | |
| House of the White Rose Boquet | Ray Wylie Hubbard | 3:23 | |
| Brokedown Palace | Shinyribs | 6:24 | |
| Call It What You Will | Joe Pug | 2:56 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| Time Waits for No Little Girls | Chip Taylor | 3:23 | |
| Nashville Is A Catfish | Joe Ely | 3:17 | |
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| Traveling Alone | Tift Merritt | 4:44 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Ruby | Dave Rawlings Machine | 4:54 | |
| Al Kaline | Jeff Daniels | 4:59 | |
| What Would You Do | Kieran Kane, Rayna Gellert | 3:25 | |
| Into the Sunlight | Malcolm Holcombe | 2:28 | |
| Down in My Hometown | The Flatlanders | 2:45 | |
| No Rust on My Spade | Otis Gibbs | 4:17 | |
| How Lucky | Kurt Vile, John Prine | 3:23 | |
| I'll Carry for You (Version) | Chip Taylor, Shaye Zadravec | 3:38 | |
| Boulevard Of Broken Dreams | Bill Bourne | 3:25 | |
| Way Over Yonder | The Small Glories | 4:41 | |
| Fishin With You (Acoustic) | Carsie Blanton | 2:17 | |
| The Old Guard | Slaid Cleaves | 3:44 | |
| Rock Salt and Nails | Willie Watson | 3:47 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Let Me Die in My Footsteps | Steep Canyon Rangers | 3:23 | |
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | |
| That's How I Feel | Dori Freeman | 2:43 | |
| She Never Spoke Spanish To Me - 2022 Remaster | Joe Ely | 3:33 | |
| You Can't Always Get What You Want | Bill Morrissey, Greg Brown | 4:46 | |
| Sweet Lucinda | Gibson Brothers | 2:45 | |
| Broke Down | Slaid Cleaves | 3:10 | |
| Gypsy Moth | Hoyt Axton | 3:15 | |
| Cold & Bitter Tears | Ted Hawkins | 2:14 | |
| Willin' | Linda Ronstadt | 3:02 | |
| Letter From Heaven | Bill Morrissey | 1:54 | |
| We'll Be Alright | Lukas Nelson and Promise of the Real | 5:01 | |