| I've Endured | Ola Belle Reed, Bud Reed, David Reed | 2:52 | |
| What of Alicia | Terry Allen | 5:03 | |
| Feeling of Beauty | Tift Merritt | 4:01 | |
| Willy the Wandering Gypsy and Me | Billy Joe Shaver | 2:29 | |
| Hundred Dollar Valentine | Chris Smither | 3:05 | |
| Brother's Keeper | Malcolm Holcombe, Iris DeMent | 2:43 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| I Don't Want Your Greenback Dollar | The Blue Sky Boys | 2:50 | |
| Let's Invite Them Over (feat. Iris DeMent) | John Prine, Iris DeMent | 2:11 | |
| I'd Jump the Mississippi | Caleb Klauder, Reeb Willms | 2:51 | |
| Too Many Memories - (feat. Emmylou Harris) | Tom Rush | 3:42 | |
| Yankee Lady | Jesse Winchester | 4:02 | |
| Espiritu Santo Bay | Kimmie Rhodes | 5:03 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Your Sweet and Shiny Eyes - 2008 Remaster | Bonnie Raitt | 2:47 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Deportees | Arlo Guthrie | 3:50 | |
| Hard Times In Babylon | Eliza Gilkyson | 4:05 | |
| The Train Carrying Jimmy Rodgers Home | Greg Brown | 3:24 | |
| The Night I Learned How Not to Pray | Iris DeMent | 4:24 | |
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| Taos to Tennessee | Tish Hinojosa | 2:57 | |
| Simple Gearle | Stacey Earle | 2:30 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| Your Long Journey | The Doc Watson Family | 2:36 | |
| Played the Game Too Long | Billy Joe Shaver | 3:23 | |
| Won't You Come and Sing for Me? - 2021 Remaster | Hazel Dickens, Alice Gerrard | 2:45 | |
| More Pretty Girls Than One | Doc & Merle Watson | 2:52 | |
| Dear Mary | Linda Thompson, Teddy Thompson, Kamila Thompson, Richard Thompson | 3:29 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| Man of Constant Sorrow | Ralph Stanley | 2:49 | |
| Waitin' for the Hard Times to Go | Jim Ringer | 3:25 | |
| That's What Makes You Strong | Jesse Winchester | 3:10 | |
| I Dream Of Highways | Hoyt Axton | 2:35 | |
| I Can't Get You Off Of My Mind | Bob Dylan | 2:55 | |
| Don't Put Her Down You Helped Put Her There | Hazel Dickens, Alice Gerrard | 3:48 | |
| Blue Moon Of Kentucky | Sarah Harmer, Jason Euringer | 2:07 | |
| One Good Year | Slaid Cleaves | 4:26 | |
| The Christian Life | The Louvin Brothers | 2:18 | |
| Holding Up the Sky | Buddy & Julie Miller | 3:09 | |
| Boy From Oklahoma | Willis Alan Ramsey | 3:54 | |
| The Bramble And The Rose | Mary McCaslin, Jim Ringer | 3:18 | |
| The Piney Wood Hills | Buffy Sainte-Marie | 3:08 | |
| Gentle River | Alison Krauss | 4:27 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| I Don't Believe You've Met My Baby | Jerry Douglas | 3:13 | |
| Why Don't You Love Me | The Secret Sisters | 2:19 | |
| Closer Still | Tish Hinojosa | 4:01 | |
| Don't Make Me Explain It | Ted Hawkins | 2:37 | |