| The Charging Sky | Jenny Lewis, The Watson Twins | 2:58 | |
| Magpie to the Morning | Neko Case | 2:56 | |
| Dixie Flyer | Randy Newman | 3:20 | |
| Let the Mystery Be | Iris DeMent | 2:50 | |
| Look at What the Light Did Now | Little Wings | 3:14 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| City of Immigrants (with Forro in the Dark) | Steve Earle | 4:18 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| Still | Great Lake Swimmers | 2:51 | |
| The Eagle And The Hawk | Bonnie Prince Billy | 1:46 | |
| Lakes Of Canada | Karen Peris, Don Peris, The Innocence Mission | 4:33 | |
| Katie Dear | The Felice Brothers | 3:58 | |
| The Big Guns | Jenny Lewis, The Watson Twins | 2:34 | |
| Until You Came Along | Golden Smog | 4:59 | |
| Our Song | Joe Henry | 6:19 | |
| Greatest Show on Earth | The Felice Brothers | 5:30 | |
| Mystifies Me - 2015 Remaster | Son Volt | 4:12 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| All The Morning Birds | Jolie Holland | 4:23 | |
| Far, Far Away - 2017 Remaster | Wilco | 3:20 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
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| Detroit or Buffalo | Barbara Keith | 4:31 | |
| Sweet Louise | Pete Molinari | 4:04 | |
| Blue Ridge Mountain | Hurray For The Riff Raff | 2:33 | |
| Rubin and Cherise | Bonnie Prince Billy | 5:46 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Damn Sam (I Love a Woman That Rains) | Ryan Adams | 2:08 | |
| Don't Wake the Scarecrow | The Felice Brothers | 4:56 | |
| I Ain't Got No Home | Billy Bragg | 3:33 | |
| Only Someone Running | Bonnie Prince Billy, Matt Sweeney | 3:13 | |
| The Well | Smog | 7:00 | |
| Grave Angels | Joe Henry | 5:31 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| Carey | Joni Mitchell | 3:02 | |
| Both Sides Now | Dave Van Ronk | 5:14 | |
| To Sing for You | Donovan | 2:42 | |
| Summer Teeth | Wilco | 3:20 | |
| Little Ann | The Felice Brothers | 3:23 | |
| I Fell into Painting Houses in Phoenix, Arizona | Richmond Fontaine | 3:27 | |
| January Song | Billy Bragg | 2:19 | |
| When I Ran off and Left Her | Vic Chesnutt | 2:54 | |
| Deep Red Bells | Neko Case | 4:03 | |
| Another Time And Place | Dave Van Ronk | 4:38 | |
| Airline To Heaven | Billy Bragg, Wilco | 4:50 | |
| Don't You Marry | Billy Bragg, Wilco | 3:14 | |
| Time Of No Reply - Orchestrated Version | Nick Drake | 2:46 | |
| Jacksonville Skyline | Whiskeytown | 3:00 | |
| Hesitating Beauty | Billy Bragg, Wilco | 3:05 | |
| Fly High | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:45 | |