| Expecting to Fly | Buffalo Springfield | 3:44 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| Strangers (2020 Stereo Remaster) | The Kinks | 3:21 | |
| Wolves | Phosphorescent | 6:14 | |
| Pulaski at Night | Andrew Bird | 4:49 | |
| The Ocean | Richard Hawley | 5:36 | |
| A Well Respected Man | The Kinks | 2:40 | |
| At Seventeen - Remastered | Janis Ian | 4:43 | |
| Bird on the Wire | Leonard Cohen | 3:23 | |
| Say It Ain't So - Remastered 2017 | Murray Head | 4:40 | |
| Velvet Gloves & Spit | Timber Timbre | 4:34 | |
| Which Side are You On? | The Almanac Singers | 2:11 | |
| Everybody's Talkin' - From "Midnight Cowboy" | Harry Nilsson | 2:43 | |
| Beneath The Rose | Micah P. Hinson | 2:56 | |
| Oh! Sweet Nuthin' - 2015 Remaster | The Velvet Underground | 7:25 | |
| Big White Cloud | John Cale | 3:29 | |
| Freedom | Richie Havens | 5:47 | |
| Better Days | Graham Nash | 3:50 | |
| Little Boxes | Pete Seeger | 1:54 | |
| Rising | Lhasa De Sela | 3:48 | |
| Helplessly Hoping - 2005 Remaster | Crosby, Stills & Nash | 2:37 | |
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| Pleasant Street | Tim Buckley | 5:17 | |
| I Want to Be Alone (Dialogue) | Jackson C. Frank | 3:18 | |
| Seabird | Alessi Brothers | 3:53 | |
| Dream Baby Dream (Long Version) | Suicide | 6:24 | |
| So Long, Marianne | Leonard Cohen | 5:36 | |
| Shake Sugaree | Elizabeth Cotten and Brenda Evans | 5:02 | |
| Bookends Theme - Reprise | Simon & Garfunkel | 1:20 | |
| Catch the Wind | Donovan | 2:53 | |
| Land: Horses / Land of a Thousand Dances / La Mer(de) | Patti Smith | 9:25 | |
| Night Comes On | Leonard Cohen | 4:40 | |
| Werewolf | Cat Power | 4:05 | |
| Some Things Last a Long Time | Daniel Johnston, Kramer | 4:54 | |
| Eid Ma Clack Shaw | Bill Callahan | 4:19 | |
| On the Road Again | Canned Heat | 3:22 | |
| Homeward Bound | Simon & Garfunkel | 2:29 | |
| From The Morning | Nick Drake | 2:30 | |
| Autopsy | Fairport Convention | 4:24 | |
| Fisherman's Blues (by Mike Scott/Steve Wickham) [Waking Ned] | Shaun Davey, The Waterboys | 4:14 | |
| Diamonds And Rust | Joan Baez | 4:46 | |
| 900 Miles | Terry Callier | 5:07 | |
| Who Knows Where The Time Goes? | Fairport Convention | 5:09 | |
| Sister Rosetta Goes Before Us | Robert Plant, Alison Krauss | 3:25 | |
| Intentional Injury - From The HBO Series True Detective | Bonnie Prince Billy | 2:24 | |
| I'll Be Your Mirror | The Velvet Underground, Nico | 2:14 | |
| One Of These Things First | Nick Drake | 4:49 | |
| If I Needed You | Townes Van Zandt | 3:44 | |
| I Think Of You | Rodríguez | 3:25 | |
| Trouble | Yusuf / Cat Stevens | 2:52 | |