| People Talkin' | Hurray For The Riff Raff | 3:52 | |
| You Must Build a Fire | Crooked Fingers | 5:38 | |
| Greatest Show on Earth | The Felice Brothers | 5:30 | |
| Up Against the Wall | The Be Good Tanyas | 3:19 | |
| Ash Wednesday | Elvis Perkins | 6:30 | |
| Northstar Blues | Magnolia Electric Co., Jason Molina | 5:08 | |
| Katie Dear | The Felice Brothers | 3:58 | |
| Out of the Picture - 2015 Remaster | Son Volt | 3:48 | |
| Muchacho's Tune | Phosphorescent | 4:19 | |
| Guilty As a Saint | Chuck Prophet | 3:52 | |
| Whiskey Bottle | Uncle Tupelo | 4:46 | |
| Far, Far Away - 2017 Remaster | Wilco | 3:20 | |
| Good Time Blues (An Outlaw's Lament) | Hurray For The Riff Raff | 5:17 | |
| Hard Bargain | Ron Sexsmith | 3:12 | |
| Looking For A Place To Land | Justin Townes Earle | 3:28 | |
| The Lucky One | Freedy Johnston | 3:09 | |
| Muzzle of Bees | Wilco | 4:52 | |
| Sunday Morning (feat. Billy Bragg & Courtney Barnett) | RocKwiz, Billy Bragg, Courtney Barnett | 2:53 | |
| Song About a Man | Deer Tick | 3:26 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Behind That Locked Door | Yim Yames | 4:17 | |
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| Down on the Lower East Side | Justin Townes Earle | 3:06 | |
| Portland - 2008 Remaster | The Replacements | 4:28 | |
| I Am Trying to Break Your Heart | Jeff Tweedy | 3:40 | |
| Lonesome Valley | Magnolia Electric Co., Jason Molina | 3:36 | |
| Corina, Corina | Conor Oberst and the Mystic Valley Band | 3:45 | |
| A Girl In Port | Okkervil River | 6:36 | |
| Through the Door | Israel Nash | 4:22 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| True Love Will Find You In The End / Spirit World Rising / Funeral Home - Live at The Vic, Chicago, IL - 10/20/17 | Daniel Johnston, Wilco | 1:24 | |
| The Big Guns | Jenny Lewis, The Watson Twins | 2:34 | |
| Lakes of Pontchartrain | The Be Good Tanyas | 4:39 | |
| Reasons To Quit | Phosphorescent | 3:13 | |
| Rogers Park | Justin Townes Earle | 4:27 | |
| Rubin and Cherise | Bonnie Prince Billy | 5:46 | |
| Throwing Your Voice | Damien Jurado | 3:01 | |
| Fatal Wound | Uncle Tupelo | 4:09 | |
| Can You Please Crawl Out Your Window? | The Hold Steady | 3:50 | |
| That's How I Got to Memphis | Karl Blau | 4:03 | |
| Speeding Motorcycle - Live at The Vic, Chicago, IL - 10/20/17 | Daniel Johnston, Wilco | 3:53 | |
| Salome | Old 97's | 4:07 | |
| What Light | Wilco | 3:35 | |
| My Flying Saucer | Billy Bragg, Wilco | 1:44 | |
| Be Kind To The Boy On The Road | Billy Bragg, Wilco | 3:42 | |
| My Hometown | Whiskeytown | 2:45 | |
| Hoping Machine | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 4:52 | |
| Ain'ta Gonna Grieve | Billy Bragg, Wilco | 4:47 | |
| She Came Along To Me | Billy Bragg, Wilco | 3:28 | |
| Hollywood Ending | Hayden | 2:54 | |
