| The Storms are on the Ocean | Larry Perkins, Alison Krauss, Bobby Osborne, Terry Eldredge | 3:30 | |
| Eulalie | Jesse Winchester | 3:43 | |
| I Should Have Said | Bap Kennedy | 3:17 | |
| When You're My Age (feat. Hillary Lindsey & Liz Rose) | Lori McKenna, Liz Rose, Hillary Lindsey | 5:11 | |
| Comin' Down in the Rain | Nanci Griffith | 3:44 | |
| Rogers Park | Justin Townes Earle | 4:27 | |
| Is It Like Today | Eliza Gilkyson | 5:49 | |
| Bless Your Foolish Heart | Jesse Winchester | 3:09 | |
| Grave Angels | Joe Henry | 5:31 | |
| Your Mother And I | Loudon Wainwright III | 2:33 | |
| The Oil Rigs at Night | The Delines | 4:23 | |
| Country Road - 2019 Remaster | James Taylor | 3:22 | |
| The Thirty-third of August | Mickey Newbury | 5:42 | |
| Boulder to Birmingham - 2003 Remaster | Emmylou Harris | 3:33 | |
| Emerald Street | Eliza Gilkyson | 3:45 | |
| Blue River | Eric Andersen | 4:45 | |
| Helpless | Crosby, Stills, Nash & Young | 3:37 | |
| Urge for Going | Joni Mitchell | 5:08 | |
| Sweet Baby James - 2019 Remaster | James Taylor | 2:53 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| Cave Man | Chris Smither | 5:23 | |
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| The Water is Wide | John Gorka | 4:28 | |
| A Case of You | k.d. lang | 5:11 | |
| Morning Song for Sally | Nanci Griffith | 4:55 | |
| Encore | Graham Nash | 3:51 | |
| Ghost Repeater | Jeffrey Foucault | 5:10 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
| Mississippi You're On My Mind | Jesse Winchester | 3:26 | |
| Man of God | Eliza Gilkyson | 4:27 | |
| Strange Boat - 2006 Remaster | The Waterboys | 3:06 | |
| The Way It Goes | Gillian Welch | 4:01 | |
| Sunday Mornin' Comin' Down | Kris Kristofferson | 4:30 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Simple Love | Alison Krauss | 4:45 | |
| It Don’t Bother Me | Robert Plant, Alison Krauss | 5:06 | |
| Julie's House | Leo Kottke | 3:23 | |
| Oh, Atlanta | Alison Krauss | 4:43 | |
| Banks Of The Pontchartrain | Nanci Griffith | 3:46 | |
| Angel Dance | Robert Plant | 3:49 | |
| Once Were Brothers | Robbie Robertson | 4:24 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Through the Morning, Through the Night | Robert Plant, Alison Krauss | 4:00 | |
| Wide River To Cross | Levon Helm | 4:51 | |
| Please Read The Letter | Robert Plant, Alison Krauss | 5:53 | |
| What Led Me To This Town | The Jayhawks | 4:09 | |
| Change Of Heart | Teddy Thompson | 3:05 | |
| Empty Hearts | Alison Krauss | 3:24 | |
| Can't Find My Way Home | Blind Faith | 3:16 | |
| Gulf Coast Highway | Nanci Griffith, Mac McAnally | 3:08 | |