| Scavenger | Lucy Kaplansky | 4:02 | |
| Americans in Corduroys | Jeffrey Foucault | 4:49 | |
| Country Road - 2019 Remaster | James Taylor | 3:22 | |
| Old Shoes | Tom Waits | 4:25 | |
| Hard Times In Babylon | Eliza Gilkyson | 4:05 | |
| I'm a Mess | Nick Lowe | 3:10 | |
| Everything Is Free | Gillian Welch | 4:47 | |
| Manhattan Moon | Lucy Kaplansky | 3:54 | |
| Helpless | k.d. lang | 4:17 | |
| Hearts and Bones | Paul Simon | 5:39 | |
| The Most Unoriginal Sin | John Hiatt & The Goners | 4:15 | |
| Snowin' on Raton | Gretchen Peters | 4:23 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| Light a Candle | Neil Young | 3:00 | |
| Song For A Deck Hands Daughter | James McMurtry | 3:30 | |
| Willin' | Little Feat | 2:54 | |
| Dangerous Fun | Jesse Winchester | 2:05 | |
| Return of the Grievous Angel - 2006 Remaster | Gram Parsons | 4:26 | |
| Rogers Park | Justin Townes Earle | 4:27 | |
| Who Holds Your Hand | Patty Larkin | 3:07 | |
| Please Stay | Warren Zevon | 3:34 | |
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| We Don't Live Here Anymore | Jakob Dylan | 4:23 | |
| Growin' Pain | Peter Wolf | 3:12 | |
| Better at Lying | Teddy Thompson, Kelly Jones | 2:54 | |
| I Ain't Got No Home | Bruce Springsteen | 3:40 | |
| One Hell Of A Life | Katell Keineg | 3:35 | |
| Old Man | The Wailin' Jennys | 3:11 | |
| Whiskey Lullaby (feat. Alison Krauss) | Brad Paisley, Alison Krauss | 4:19 | |
| When You're My Age (feat. Hillary Lindsey & Liz Rose) | Lori McKenna, Liz Rose, Hillary Lindsey | 5:11 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| The Last Bus | Zoe Muth | 5:59 | |
| Still Not Home | Tift Merritt | 3:48 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| The Long Black Veil (with Mick Jagger) | The Chieftains, Mick Jagger | 3:37 | |
| The Ransom | Madison Violet | 3:37 | |
| Polly Come Home | Robert Plant, Alison Krauss | 5:36 | |
| I Will | Alison Krauss, Tony Furtado | 4:04 | |
| Wild Horses | The Flying Burrito Brothers | 6:20 | |
| Black Sheep | Blackie & The Rodeo Kings, Serena Ryder | 5:28 | |
| Lord Protect My Child | Susan Tedeschi | 4:44 | |
| The Weary Kind | Ryan Bingham | 4:18 | |
| Lucky Now | Ryan Adams | 2:52 | |
| My Heart Would Know | Robert Plant, Alison Krauss | 2:58 | |
| Trouble Over Me | Tift Merritt | 5:08 | |
| Stranger In A Strange Land | Leon Russell | 4:02 | |
| Roll On | The Little Willies | 3:06 | |
| Lay Down Your Weary Tune | Tim O'Brien | 3:28 | |