| The Thirty-third of August | Mickey Newbury | 5:42 | |
| This Old Road | Kris Kristofferson | 3:59 | |
| Coast | Eliza Gilkyson | 3:25 | |
| Annabelle | Gillian Welch | 4:04 | |
| The Oil Rigs at Night | The Delines | 4:23 | |
| Helpless | k.d. lang | 4:17 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| Wildflowers | Tom Petty | 3:10 | |
| Scavenger | Lucy Kaplansky | 4:02 | |
| Ol' 55 | Tom Waits | 3:56 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| Billy 4 | Gretchen Peters | 5:36 | |
| People My Age | John Gorka | 2:16 | |
| All the Way to Amsterdam | Greg Trooper | 2:59 | |
| Truth For A Truth | Jakob Dylan | 3:35 | |
| When The Night Was Young | Robbie Robertson | 5:04 | |
| My Favorite Picture of You | Guy Clark | 3:32 | |
| Country Road - 2019 Remaster | James Taylor | 3:22 | |
| San Diego Serenade | Tom Waits | 3:30 | |
| Snowin' on Raton | Gretchen Peters | 4:23 | |
| Tambourine Man | Gene Clark | 5:37 | |
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| Salford Sunday | Richard Thompson | 4:08 | |
| Owensboro - Remastered Version | Natalie Merchant | 4:25 | |
| You Got Me Singing | Leonard Cohen | 3:31 | |
| The Way It Goes | Gillian Welch | 4:01 | |
| Indian Queens | Nick Lowe | 3:52 | |
| The Matador | Gretchen Peters | 4:18 | |
| These Days | Gregg Allman | 3:57 | |
| A Song For You | Leon Russell | 4:08 | |
| High Lonesome Sound - Bluegrass Version | Vince Gill, The Union Station, Alison Krauss | 3:09 | |
| Trouble Over Me | Tift Merritt | 5:08 | |
| Till The Rivers All Run Dry | Pete Townshend, Ronnie Lane | 3:52 | |
| Too Much Heaven (feat. Alison Krauss) | Barry Gibb, Alison Krauss | 3:39 | |
| Waltzing's For Dreamers | Richard Thompson | 4:06 | |
| That's What Makes You Strong | Jesse Winchester | 3:10 | |
| Thank You | Jimmy Page, Robert Plant | 5:48 | |
| I'll Fly Away | Gillian Welch, Alison Krauss | 3:57 | |
| Rich Woman | Robert Plant, Alison Krauss | 4:03 | |
| Promises | Eric Clapton | 3:01 | |
| You Led Me to The Wrong | Robert Plant, Alison Krauss | 4:17 | |
| California Stars | Billy Bragg, Wilco | 4:58 | |
| Stranger In A Strange Land | Leon Russell | 4:02 | |
| Just When I Needed You Most | Dolly Parton, Alison Krauss, John Sebastian | 4:36 | |
| Till I Gain Control Again - Live | Alison Krauss | 5:30 | |
| Graduation Day | Chris Isaak | 3:10 | |
| Wild Horses | The Flying Burrito Brothers | 6:20 | |
| It Makes No Difference - Remastered 2000 | The Band | 6:34 | |
| Fortune Teller | Robert Plant, Alison Krauss | 4:30 | |
| Lucky Now | Ryan Adams | 2:52 | |