| Destroyer | Crooked Fingers | 5:18 | ||
| In a Future Age | Wilco | 2:57 | ||
| Full Moon in My Soul | Robyn Hitchcock | 3:02 | ||
| Okkervil River Song | Okkervil River | 5:54 | ||
| I Looked All over Town | The Magnetic Fields | 2:39 | ||
| Lucinda Williams | Vic Chesnutt | 2:47 | ||
| Baby Learns to Crawl | Paul Westerberg | 2:46 | ||
| Weary Arms | Crooked Fingers | 2:29 | ||
| Never Anyone But You | The Clientele | 5:30 | ||
| Grave Angels | Joe Henry | 5:31 | ||
| A Girl In Port | Okkervil River | 6:36 | ||
| Anna Leigh | The Sadies | 3:21 | ||
| Black Rain, Black Rain | A.A. Bondy | 3:14 | ||
| Love At First Feel | Mark Kozelek | 2:12 | ||
| Gun | Uncle Tupelo | 3:40 | ||
| When We Become | Clem Snide | 5:17 | ||
| Ease Your Feet in the Sea | Belle and Sebastian | 3:35 | ||
| Twenty Cycles To The Ground | Jason Molina, Will Johnson | 3:07 | ||
| What Are You? | Bonnie Prince Billy, Matt Sweeney | 2:38 | ||
| Lost Love | Jeff Tweedy | 2:28 | ||
| Atlanta | Centro-matic | 3:52 | ||
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| Another Velvet Nightmare | Frank Black | 4:25 | ||
| Empty Hearted Town | Warren Zevon | 3:06 | ||
| Belles | Vetiver | 5:06 | ||
| Come Indiana Through The Smoke | Okkervil River | 4:45 | ||
| Mrs. Juliette Low | Phosphorescent | 3:03 | ||
| Nothing to No One | Paul Westerberg | 2:11 | ||
| New Moon | Tweedy, Jeff Tweedy | 3:39 | ||
| It Wasn't Me | Jenny Lewis, The Watson Twins | 4:12 | ||
| Friends Like Those | Robert Ellis | 4:07 | ||
| Honey Don't Think | Grant Lee Buffalo | 2:43 | ||
| Dodge | Vic Chesnutt | 4:09 | ||
| Warm (When The Sun Has Died) | Jeff Tweedy | 2:18 | ||
| Road to Ronderlin | Vetiver | 2:25 | ||
| Slate | Uncle Tupelo | 3:24 | ||
| All of Your Might | Jay Farrar | 3:48 | ||
| Acid Tongue | Jenny Lewis | 3:50 | ||
| Hey Joe - Session at The loft, Chicago, IL - 10/19/17 | Daniel Johnston, Wilco | 2:35 | ||
| Theologians | Wilco | 3:32 | ||
| Where Were You | Vic Chesnutt | 4:44 | ||
| Casper The Friendly Ghost - Live at The Vic, Chicago, IL - 10/20/17 | Daniel Johnston, Wilco | 2:47 | ||
| Wonderful Life | The Felice Brothers | 4:02 | ||
| Avenues | Whiskeytown | 2:31 | ||
| The Hardest Part | Ryan Adams & The Cardinals | 2:51 | ||
| Don't Get Down | Hayden | 3:19 | ||
| Jailcell Blues | Billy Bragg, Wilco | 2:23 | ||
| Rider On The Wheel | Nick Drake | 2:37 | ||
| Jacksonville Skyline | Whiskeytown | 3:00 | ||
| Ain'ta Gonna Grieve | Billy Bragg, Wilco | 4:47 | ||
