| Changed the Locks | Lucinda Williams | 3:43 | |
| Old Friend | Lyle Lovett | 3:13 | |
| Find the Cost of Freedom | Crosby, Stills, Nash & Young | 1:58 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| The Last Waltz Suite: The Weight (feat. The Staples) | The Band, The Staple Singers | 4:35 | |
| Fare Thee Well (Dink's Song) | Oscar Isaac, Marcus Mumford | 3:00 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| El Amor De Mi Vida | Warren Zevon | 3:33 | |
| Miles Away | Josh Ritter | 3:53 | |
| Harlem River Blues | Justin Townes Earle | 2:48 | |
| Sweet Baby James - 2019 Remaster | James Taylor | 2:53 | |
| Beautiful World | Colin Hay | 4:04 | |
| Hurdy Gurdy Man | Donovan | 3:13 | |
| Astral Weeks - 1999 Remaster | Van Morrison | 7:06 | |
| Ol' 55 | Tom Waits | 3:56 | |
| Catch the Wind | Donovan | 2:53 | |
| Some Day Soon | Alexi Murdoch | 4:47 | |
| Everybody Knows | The Jayhawks | 4:10 | |
| Mutineer - 2008 Remaster | Warren Zevon | 3:16 | |
| Sweet Thing - 1999 Remaster | Van Morrison | 4:25 | |
| Atlantis | Donovan | 5:02 | |
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| The Boxer feat. Mumford & Sons and Paul Simon | Jerry Douglas, Paul Simon, Mumford & Sons | 4:05 | |
| Me & Magdalena | The Monkees | 3:33 | |
| Romeo's Tune | Steve Forbert | 3:32 | |
| Teach Your Children | Crosby, Stills, Nash & Young | 2:53 | |
| Private Conversation | Lyle Lovett | 4:32 | |
| Into My Arms | Nick Cave & The Bad Seeds | 4:16 | |
| Midnight Rider | Gregg Allman | 4:27 | |
| Alison | Elvis Costello | 3:24 | |
| Refugee | Tom Petty and the Heartbreakers | 3:21 | |
| Till It Shines | Bob Seger | 3:54 | |
| Against The Wind | Bob Seger | 5:33 | |
| Walt Whitman's Niece | Billy Bragg, Wilco | 3:53 | |
| Please Read The Letter | Robert Plant, Alison Krauss | 5:53 | |
| Vincent | Don McLean | 4:03 | |
| Learning To Fly | Tom Petty and the Heartbreakers | 4:02 | |
| Free Fallin' | Tom Petty | 4:16 | |
| La Cienega Just Smiled | Ryan Adams | 5:01 | |
| Melissa | Allman Brothers Band | 3:55 | |
| Mercy Now | Mary Gauthier | 5:50 | |
| Wild Horses - 2009 Mix | The Rolling Stones | 5:41 | |
| 2 Kool 2 Be 4-Gotten | Lucinda Williams | 4:42 | |
| The Rescue Blues | Ryan Adams | 3:38 | |
| Stewart's Coat | Rickie Lee Jones | 4:31 | |
| I Won't Back Down | Tom Petty | 2:58 | |
| Jessica | Allman Brothers Band | 7:31 | |
| Let My Love Open The Door | Pete Townshend | 2:44 | |
| Gone Gone Gone (Done Moved On) | Robert Plant, Alison Krauss | 3:32 | |
| Birds And Ships | Billy Bragg, Wilco, Natalie Merchant | 2:15 | |