| I Can Help | Charley Crockett | 3:38 | |
| Workin’s Too Hard | Rayna Gellert | 3:36 | |
| Sweet Baby James - 2019 Remaster | James Taylor | 2:53 | |
| Blue Ridge Mountain | Hurray For The Riff Raff | 2:33 | |
| Over the Red Cedar | Charlie Parr | 4:19 | |
| Other Side of Town - Live | John Prine | 4:53 | |
| Oh What a Beautiful World | Rodney Crowell | 5:07 | |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| Goin' to Acapulco | Jim James, Calexico | 4:58 | |
| Speed Of The Sound Of Loneliness | John Prine | 3:28 | |
| Live Forever | Billy Joe Shaver | 2:49 | |
| Irene (Ravin' Bomb) | Ian Noe | 3:58 | |
| Send The Sun | Nikki Lane | 2:57 | |
| My Favorite Picture of You | Guy Clark | 3:32 | |
| Lovin' in My Baby's Eyes | Taj Mahal | 2:40 | |
| Dead Skunk | Loudon Wainwright III | 3:05 | |
| The Needle and the Damage Done | Neil Young | 2:02 | |
| Easy Rider | Eddie Berman | 3:49 | |
| Golden Embers | Watchhouse | 4:45 | |
| Million Dollar Bill | Middle Brother, John McCauley, Matthew Vasquez, Taylor Goldsmith | 4:03 | |
| Life Is Beautiful | Keb' Mo' | 4:16 | |
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| Ooh La La | Faces | 3:34 | |
| I Hate It When That Happens to Me | John Prine | 2:49 | |
| The Last Thing on My Mind | Tom Paxton | 3:06 | |
| Old Ties and Companions | Watchhouse | 3:08 | |
| Angel from Montgomery - 2008 Remaster | Bonnie Raitt | 3:59 | |
| Travelers Paradise | The Cactus Blossoms | 2:58 | |
| First Air of Autumn | Drive-By Truckers | 3:30 | |
| You Got to Me | James McMurtry | 5:23 | |
| My Winding Wheel | Ryan Adams | 3:12 | |
| Rocky Mountain High | John Denver | 4:43 | |
| Knockin' on Your Screen Door | John Prine | 2:19 | |
| Please Read The Letter | Robert Plant, Alison Krauss | 5:53 | |
| You Ain't Going Nowhere | Nitty Gritty Dirt Band | 3:52 | |
| Time Stands | Nathaniel Rateliff | 3:52 | |
| Postcards From Hell | The Wood Brothers | 4:44 | |
| Farewell Angelina | Tim O'Brien | 4:23 | |
| Mercy Now | Mary Gauthier | 5:50 | |
| (I’m Gonna Get Over This) Some Day | Logan Ledger | 2:52 | |
| California Stars | Billy Bragg, Wilco | 4:58 | |
| This Must Be The Place | Iron & Wine, Ben Bridwell | 3:32 | |
| Poncho & Lefty | Townes Van Zandt | 3:40 | |
| The Night They Drove Old Dixie Down | The Band | 3:31 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Dancing With The Women At The Bar | Whiskeytown | 4:38 | |
| Sam Stone | Nathaniel Rateliff, John Prine | 4:17 | |
| Over The Hill | John Martyn | 2:52 | |
| Jeremiah | Sierra Ferrell | 3:03 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |