| Officer Down | Carolyn Mark, NQ Arbuckle | 3:57 | |
| Lonesome Valley | Magnolia Electric Co. | 3:36 | |
| Strange Goodbye | Frank Black | 2:09 | |
| Fair Annie | Bonny Light Horseman, Anaïs Mitchell, Eric D. Johnson, Josh Kaufman | 3:00 | |
| Kid Codeine | The Delines | 3:19 | |
| Corncob | Martin Courtney | 4:07 | |
| Country Song Upside-down | Wilco | 2:46 | |
| Before You Go | Jesse Malin | 3:25 | |
| El Paso | Calexico | 2:33 | |
| Out Of Range, Pt. 2 | My Morning Jacket | 4:26 | |
| Can't See Stars (feat. Kevin Morby) | Erin Rae, Kevin Morby | 3:36 | |
| South For The Winter (feat. Matt Berninger) | Adia Victoria, Matt Berninger | 3:15 | |
| The Moon Tonight | Dan Reeder, Todd Snider | 2:24 | |
| I Am Trying to Break Your Heart | Jeff Tweedy | 3:40 | |
| Ramblin' With The Day | Rose City Band | 3:38 | |
| Birthdays | Craig Finn | 3:04 | |
| All the Good | The Sadies | 3:39 | |
| Valley | Kevin Morby | 4:04 | |
| Land of Yesterdays | The Felice Brothers | 5:19 | |
| War | Waxahatchee | 3:10 | |
| Rolling Mills Are Burning Down | Jake Xerxes Fussell | 5:18 | |
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| Ten Dead | Wilco | 3:55 | |
| A Secret Still to Be Betrayed | Daniel Romano, The Outfit | 4:24 | |
| Message to Belial | The Sadies | 3:15 | |
| You Don't See Me Crying | Beachwood Sparks, GospelbeacH | 4:00 | |
| Maestranza - Solstice Version | Fleet Foxes | 2:55 | |
| Hearts Hard to Find | Wilco | 3:27 | |
| The Man Who Loves The Rain | Robyn Hitchcock | 4:09 | |
| Clean Air | Hand Habits | 3:08 | |
| Slate | Uncle Tupelo | 3:24 | |
| Breast of Glass | Jake Xerxes Fussell | 4:01 | |
| Occasional Rain | The War On Drugs | 4:54 | |
| Fleur de Lis | Bonny Light Horseman, Anaïs Mitchell, Eric D. Johnson, Josh Kaufman | 4:23 | |
| Funeral Home - Live at The Vic, Chicago, IL - 10/20/17 | Daniel Johnston, Wilco | 3:10 | |
| You Gave Me The Key | Julie Doiron | 2:47 | |
| Infinite Surprise | Wilco | 5:43 | |
| Stay Down, Man | Dan Reeder | 1:54 | |
| Place Called Love | Ron Sexsmith | 2:39 | |
| Streets of Philadelphia | Waxahatchee | 4:09 | |
| Gullwing Doors | Fruit Bats | 4:35 | |
| Curtis & Shepard | Craig Finn | 4:31 | |
| After the Rain | Chuck Prophet | 3:35 | |
| Bottle Episodes | The New Pornographers | 4:12 | |
| Somebody Else | Sarah Shook & the Disarmers | 3:01 | |
| Give Me Fifteen | Aimee Mann | 2:42 | |
| In Spite Of Me | Matt Berninger | 2:20 | |
| At My Window Sad And Lonely | Billy Bragg, Wilco | 3:27 | |
| Teeth Marks | S.G. Goodman | 3:37 | |
| All My Love Is Coming Back To Me | S.G. Goodman | 3:29 | |